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【结 构 式】 
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【分子编号】17922 【品名】2-methyl-3-butyn-2-ol; 3-Methyl butynol 【CA登记号】115-19-5 |
【 分 子 式 】C5H8O 【 分 子 量 】84.11792 【元素组成】C 71.39% H 9.59% O 19.02% |
合成路线1
该中间体在本合成路线中的序号：(III)The ozonolysis of the terminal double bond of (I) gives the aldehyde (II), which is condensed with the acetylenic alcohol (II) by means of Zn(OTf)2 in the presence of (+)-N-methylephedrine to yield the chiral acetylenic diol (IV). The reaction of (IV) with benzoyl chloride and TEA affords the monobenzoate (V), which is treated with K2CO3 and LiAlH4 to provide the chiral allyl alcohol derivative (VI). The cyclization of (VI) with the phosphonate (VII) by means of Et-MgBr in isopropanol/dichloromethane gives the isooxazoline (VIII), which is treated with Tbdms-OTf to yield the corresponding silyl ether (IX). The condensation of (IX) with 2-methylthiazole-4-carbaldehyde (X) by means of DBU and LiCl affords the isooxazoline derivative (XI), which is treated with SmI2, Et3B and NaBH4 to cleave the isoxazoline ring and yield the diol (XII). The reaction of (XII) with SOCl2, TEA and TBAF affords the chiral epoxide (XIII), which is silylated with Tes-Cl and TEA to provide the silyl ether (XIV). The selective hydrolysis of the primary silyl ether of (XIV) with HOAc in THF/water gives the primary alcohol (XV), which is oxidized with TPAP and NMO in dichloromethane to yield the corresponding aldehyde (XVI).
| 【1】 Bode, J.W.; Carreira, E.M.; Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition. J Am Chem Soc 2001, 123, 18, 3611. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 49304 | triisopropyl[[(2S)-2-methyl-6-heptenyl]oxy]silane; (2S)-2-methyl-6-heptenyl triisopropylsilyl ether | C17H36OSi | 详情 | 详情 | |
| (II) | 49305 | (5S)-5-methyl-6-[(triisopropylsilyl)oxy]hexanal | C16H34O2Si | 详情 | 详情 | |
| (III) | 17922 | 2-methyl-3-butyn-2-ol; 3-Methyl butynol | 115-19-5 | C5H8O | 详情 | 详情 |
| (IV) | 49306 | (5R,9S)-2,9-dimethyl-10-[(triisopropylsilyl)oxy]-3-decyne-2,5-diol | C21H42O3Si | 详情 | 详情 | |
| (V) | 49307 | (1R)-4-hydroxy-4-methyl-1-[(4S)-4-methyl-5-[(triisopropylsilyl)oxy]pentyl]-2-pentynyl benzoate | C28H46O4Si | 详情 | 详情 | |
| (VI) | 49308 | (3R,7S)-7-methyl-8-[(triisopropylsilyl)oxy]-1-octen-3-ol | C18H38O2Si | 详情 | 详情 | |
| (VII) | 49286 | diethyl 2-(hydroxyimino)-1-methylethylphosphonate | C7H16NO4P | 详情 | 详情 | |
| (VIII) | 49309 | diethyl 1-((5R)-5-[(1R,5S)-1-hydroxy-5-methyl-6-[(triisopropylsilyl)oxy]hexyl]-4,5-dihydro-3-isoxazolyl)ethylphosphonate | C25H52NO6PSi | 详情 | 详情 | |
| (IX) | 44455 | 2-methyl-1,3-thiazole-4-carbaldehyde | C5H5NOS | 详情 | 详情 | |
| (X) | 49310 | diethyl 1-((5R)-5-[(1R,5S)-1-[[tert-butyl(dimethyl)silyl]oxy]-5-methyl-6-[(triisopropylsilyl)oxy]hexyl]-4,5-dihydro-3-isoxazolyl)ethylphosphonate | C31H66NO6PSi2 | 详情 | 详情 | |
| (XI) | 49311 | (5R)-5-[(1R,5S)-1-[[tert-butyl(dimethyl)silyl]oxy]-5-methyl-6-[(triisopropylsilyl)oxy]hexyl]-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,5-dihydroisoxazole; tert-butyl(dimethyl)silyl (1R,5S)-5-methyl-1-[(5R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,5-dihydro-5-isoxazolyl]-6-[(triisopropylsilyl)oxy]hexyl ether | C32H60N2O3SSi2 | 详情 | 详情 | |
| (XII) | 49312 | (E,3S,5R,6R,10S)-6-[[tert-butyl(dimethyl)silyl]oxy]-2,10-dimethyl-1-(2-methyl-1,3-thiazol-4-yl)-11-[(triisopropylsilyl)oxy]-1-undecene-3,5-diol | C32H63NO4SSi2 | 详情 | 详情 | |
| (XIII) | 49313 | (2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-1-((2S,3R)-3-[(4S)-4-methyl-5-[(triisopropylsilyl)oxy]pentyl]oxiranyl)-3-buten-2-ol | C26H47NO3SSi | 详情 | 详情 | |
| (XIV) | 49314 | (2S)-2-methyl-5-((2R,3S)-3-[(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)pentyl triisopropylsilyl ether; 2-methyl-4-[(E,3S)-2-methyl-4-((2S,3R)-3-[(4S)-4-methyl-5-[(triisopropylsilyl)oxy]pentyl]oxiranyl)-3-[(triethylsilyl)oxy]-1-butenyl]-1,3-thiazole | C32H61NO3SSi2 | 详情 | 详情 | |
| (XV) | 49315 | (2S)-2-methyl-5-((2R,3S)-3-[(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)-1-pentanol | C23H41NO3SSi | 详情 | 详情 | |
| (XVI) | 49316 | (2S)-2-methyl-5-((2R,3S)-3-[(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)pentanal | C23H39NO3SSi | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)The protection of 2(S)-methyl-6-hepten-1-ol (I) with Tes-Cl gives the silyl ether (II), which is oxidized by known methods to yield the aldehyde (III). The condensation of (III) with the acetylenic alcohol (IV) by means of Zn(OTf)2 and TEA to afford the acetylenic diol (V), which is selectively monobenzoylated with benzoyl chloride and TEA, providing the benzoate (VI). Extrusion of acetone from (VI) by means of K2CO3 in refluxing toluene gives the chiral octyne derivative (VII), which is reduced and debenzoylated with LiAlH4 in ethyl ether to yield the unsaturated alcohol (VIII). The condensation of (VIII) with the phosphonate (IX) by means of Et-MgBr affords the isoxazoline (X), which is treated with Tbdms-OTf and DIEA to provide the silyl ether (XI). The condensation of the phosphonate (XI) with 2-methylthiazole-4-carbaldehyde (XII) gives the adduct (XIII), which is treated with SmI2 to open the isoxazoline ring and yield the beta-hydroxy ketone (XIV). The reduction of (XIV) by means of BEt3 and NaBH4 affords the beta-diol (XV), which is treated with SOCl2 and TEA to provide the cyclic sulfite (XVI). The treatment of (XVI) with TBAF in refluxing THF/water gives the chiral epoxide (XVII), which is silylated with Tes-Cl and TEA to yield the bis silyl ether (XVIII). The selective deprotection of the primary silyl ether of (XVIII) by means of Ac-OH in THF/water affords the primary alcohol (XIX).
| 【1】 Bode, J.W.; Carreira, E.M.; Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies. J Org Chem 2001, 66, 19, 6410. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 27184 | (2S)-2-methyl-6-hepten-1-ol | C8H16O | 详情 | 详情 | |
| (II) | 49304 | triisopropyl[[(2S)-2-methyl-6-heptenyl]oxy]silane; (2S)-2-methyl-6-heptenyl triisopropylsilyl ether | C17H36OSi | 详情 | 详情 | |
| (III) | 49305 | (5S)-5-methyl-6-[(triisopropylsilyl)oxy]hexanal | C16H34O2Si | 详情 | 详情 | |
| (IV) | 17922 | 2-methyl-3-butyn-2-ol; 3-Methyl butynol | 115-19-5 | C5H8O | 详情 | 详情 |
| (V) | 49306 | (5R,9S)-2,9-dimethyl-10-[(triisopropylsilyl)oxy]-3-decyne-2,5-diol | C21H42O3Si | 详情 | 详情 | |
| (VI) | 49307 | (1R)-4-hydroxy-4-methyl-1-[(4S)-4-methyl-5-[(triisopropylsilyl)oxy]pentyl]-2-pentynyl benzoate | C28H46O4Si | 详情 | 详情 | |
| (VII) | 60464 | (1R)-1-{(4S)-4-methyl-5-[(triisopropylsilyl)oxy]pentyl}-2-propynyl benzoate | C25H40O3Si | 详情 | 详情 | |
| (VIII) | 49308 | (3R,7S)-7-methyl-8-[(triisopropylsilyl)oxy]-1-octen-3-ol | C18H38O2Si | 详情 | 详情 | |
| (IX) | 60465 | C4H8ClNO4PT | 详情 | 详情 | ||
| (X) | 60466 | C22H45NO6PSiT | 详情 | 详情 | ||
| (XI) | 60467 | C28H59NO6PSi2T | 详情 | 详情 | ||
| (XII) | 44455 | 2-methyl-1,3-thiazole-4-carbaldehyde | C5H5NOS | 详情 | 详情 | |
| (XIII) | 49311 | (5R)-5-[(1R,5S)-1-[[tert-butyl(dimethyl)silyl]oxy]-5-methyl-6-[(triisopropylsilyl)oxy]hexyl]-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,5-dihydroisoxazole; tert-butyl(dimethyl)silyl (1R,5S)-5-methyl-1-[(5R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,5-dihydro-5-isoxazolyl]-6-[(triisopropylsilyl)oxy]hexyl ether | C32H60N2O3SSi2 | 详情 | 详情 | |
| (XIV) | 60468 | (E,5R,6R,10S)-6-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-2,10-dimethyl-1-(2-methyl-1,3-thiazol-4-yl)-11-[(triisopropylsilyl)oxy]-1-undecen-3-one | C32H61NO4SSi2 | 详情 | 详情 | |
| (XV) | 49312 | (E,3S,5R,6R,10S)-6-[[tert-butyl(dimethyl)silyl]oxy]-2,10-dimethyl-1-(2-methyl-1,3-thiazol-4-yl)-11-[(triisopropylsilyl)oxy]-1-undecene-3,5-diol | C32H63NO4SSi2 | 详情 | 详情 | |
| (XVI) | 60469 | (4R,6S)-4-{(1R,5S)-1-{[tert-butyl(dimethyl)silyl]oxy}-5-methyl-6-[(triisopropylsilyl)oxy]hexyl}-6-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-1,3,2lambda~4~-dioxathian-2-one | C32H61NO5S2Si2 | 详情 | 详情 | |
| (XVII) | 60470 | (2S,3E)-1-{(2S,3R)-3-[(4S)-5-hydroxy-4-methylpentyl]oxiranyl}-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-buten-2-ol | C17H27NO3S | 详情 | 详情 | |
| (XVIII) | 60471 | (2S)-2-methyl-5-((2R,3S)-3-{(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl}oxiranyl)pentyl triethylsilyl ether; 2-methyl-4-{(E,3S)-2-methyl-4-((2S,3R)-3-{(4S)-4-methyl-5-[(triethylsilyl)oxy]pentyl}oxiranyl)-3-[(triethylsilyl)oxy]-1-butenyl}-1,3-thiazole | C29H55NO3SSi2 | 详情 | 详情 | |
| (XIX) | 49315 | (2S)-2-methyl-5-((2R,3S)-3-[(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)-1-pentanol | C23H41NO3SSi | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(X)Treatment of 5-bromo-3-pyridinecarboxylic acid (I) with thionyl chloride in 1,2-dichloroethane (DCE) gives acid chloride hydrochloride (II), which is converted to ester (III) on treatment with ethanol in DCE. Claisen condensation of ester (III) with N-vinylpyrrolidinone (IV) in the presence of littium bis(trimethylsilyl)amide followed by refluxing in aqueous hydrochloric acid gives the pyrroline (V). The reduction of pyrroline (V) with sodium borohydride in the presence of the chiral auxiliary N-carbobenzyloxy-L-proline yields the enantiomerically enriched (S)-pyrrolidine (VI) with an e.e. of 30%. This compound is reductively methylated in a mixture of aqueous formaldehyde and formic acid, and the resulting N-methylpyrrolidine (VII) is converted to the di-p-toluoyl-D-tartaric acid salt, and recrystallized from ethanol-ethyl acetate to increase the e.e. to 90%. The free amine (VII) is coupled with trimethylsilyl acetylene (VIII), in the presence of bis(triphenylphosphine)palladium dichloride, cuprous iodide, and triethylamine in THF. The resulting compound (IX) is treated with cesium carbonate in refluxing methanol to remove the trimethylsilyl group, and finally converted to the maleate salt on treatment with maleic acid in methanol.
| 【1】 McCallum, J.S.; Cosford, N.D.P.; McDonald, I.A.; Herbaut, A.; Bleicher, L.S.; A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y). J Org Chem 1998, 63, 4, 1109. |
| 【2】 Cosford, N.D.P.; et al.; (S)-(-)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y): A novel anti-parkinsonian agent with selectivity for neuronal nicotinic acetylcholine receptors. J Med Chem 1996, 39, 17, 3225. |
| 【3】 McDonald, I.A.; Whitten, J.P.; Cosford, N.D. (SIBIA Neurosciences, Inc.); Pyridine modulators of acetylcholine receptors. EP 0739342; JP 1997508648; US 5594011; WO 9615123 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 17913 | 5-Bromonicotinic acid | 20826-04-4 | C6H4BrNO2 | 详情 | 详情 |
| (II) | 14130 | 5-Bromonicotinoyl chloride | 39620-02-5 | C6H3BrClNO | 详情 | 详情 |
| (III) | 17915 | Ethyl 5-bromonicotinate | 20986-40-7 | C8H8BrNO2 | 详情 | 详情 |
| (IV) | 17916 | N-Vinyl-2-Pyrrolidinone; 1-vinyl-2-pyrrolidinone | 88-12-0 | C6H9NO | 详情 | 详情 |
| (V) | 17917 | 3-bromo-5-(3,4-dihydro-2H-pyrrol-5-yl)pyridine | C9H9BrN2 | 详情 | 详情 | |
| (VI) | 17918 | 3-bromo-5-[(2R)pyrrolidinyl]pyridine | C9H11BrN2 | 详情 | 详情 | |
| (VII) | 17919 | 3-bromo-5-[(2R)-1-methylpyrrolidinyl]pyridine | C10H13BrN2 | 详情 | 详情 | |
| (VIII) | 23897 | ethynyl(trimethyl)silane；trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
| (IX) | 17921 | 3-[(2R)-1-methylpyrrolidinyl]-5-[2-(trimethylsilyl)ethynyl]pyridine | C15H22N2Si | 详情 | 详情 | |
| (X) | 17922 | 2-methyl-3-butyn-2-ol; 3-Methyl butynol | 115-19-5 | C5H8O | 详情 | 详情 |
| (XI) | 17923 | 2-methyl-4-[5-[(2R)-1-methylpyrrolidinyl]-3-pyridinyl]-3-butyn-2-ol | C15H20N2O | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)Treatment of 2-methyl-3-butyn-2-ol (I) with trifluoroacetic anhydride and DBU gave trifluoroacetate (II), which was condensed with 4-bromophenol (III) in the presence of CuCl2 to afford propargyl ether (IV). Cyclization of (IV) in N,N-diethylaniline at 185 C produced benzopyran (V). The required sulfonyl group was introduced in (V) by lithium-bromine exchange, followed by reaction with sulfur dioxide to give the lithium sulfinate (VI), and then oxidation to the sulfonyl chloride (VII) by means of sulfuryl chloride (1). Subsequent treatment of (VII) with diisobutylamine yielded sulfonamide (VIII). Asymmetric epoxidation of (VIII) using sodium hypochlorite and (S,S)(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino-manganese(III) chloride (Jacobsen's catalyst) gave rise to epoxide (IX), which was opened with ammonium hydroxide to furnish the trans aminoalcohol (X). Finally, coupling of (X) with N-chlorophenyl-N'-cyanothiourea (XI) in the presence of EDC provided the title cyanoguanidine derivative.
| 【1】 Grover, G.J.; Ding, C.Z.; Miller, A.V.; Rovnyak, G.C.; Ahmed, S.Z.; Misra, R.N.; Normandin, D.E.; Atwal, K.S.; Kelly, Y.; Sleph, P.G.; Cardioselective antiischemic ATP-sensitive potassium channel (KATP) openers. 6. Effect of modifications at C6 of benzopyranyl cyanoguanidines. J Med Chem 1999, 42, 18, 3711. |
| 【2】 Ding, C.Z.; Atwal, K.S. (Bristol-Myers Squibb Co.); Sulfonamido substd. benzopyran potassium channel activators. CA 2178353; EP 0747374; JP 1997003035; US 5869478 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 33862 | trifluoroacetic anhydride | 407-25-0 | C4F6O3 | 详情 | 详情 | |
| (I) | 17922 | 2-methyl-3-butyn-2-ol; 3-Methyl butynol | 115-19-5 | C5H8O | 详情 | 详情 |
| (II) | 34888 | 1,1-dimethyl-2-propynyl 2,2,2-trifluoroacetate | C7H7F3O2 | 详情 | 详情 | |
| (III) | 25313 | 4-bromophenol | 106-41-2 | C6H5BrO | 详情 | 详情 |
| (IV) | 34889 | 1-bromo-4-[(1,1-dimethyl-2-propynyl)oxy]benzene; 4-bromophenyl 1,1-dimethyl-2-propynyl ether | C11H11BrO | 详情 | 详情 | |
| (V) | 34890 | 6-bromo-2,2-dimethyl-2H-chromene | C11H11BrO | 详情 | 详情 | |
| (VI) | 34891 | lithium 2,2-dimethyl-2H-chromene-6-sulfinate | C11H11LiO3S | 详情 | 详情 | |
| (VII) | 34892 | 2,2-dimethyl-2H-chromene-6-sulfonyl chloride | C11H11ClO3S | 详情 | 详情 | |
| (VIII) | 34893 | N,N-diisobutyl-2,2-dimethyl-2H-chromene-6-sulfonamide | C19H29NO3S | 详情 | 详情 | |
| (IX) | 34894 | (1aS,7bS)-N,N-diisobutyl-2,2-dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-sulfonamide | C19H29NO4S | 详情 | 详情 | |
| (X) | 34895 | (3S,4R)-4-amino-3-hydroxy-N,N-diisobutyl-2,2-dimethyl-3,4-dihydro-2H-chromene-6-sulfonamide | C19H32N2O4S | 详情 | 详情 | |
| (XI) | 34896 | N-(4-chlorophenyl)-N'-cyanothiourea | C8H6ClN3S | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(II)Palladium-catalyzed coupling of 2-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (I) with 2-methyl-3-butyn-2-ol (II) provided adduct (III). Subsequent cleavage of the propargyl alcohol of (III) with KOH in toluene gave the free acetylene (IV). Lithiation of (IV), followed by quenching with ethyl chloroformate, yielded the aryl propiolic ester (V). Conjugate addition to (V) of the in situ-generated lithium dimethylcuprate gave the Z-crotonate (VI), which was further reduced to the allylic alcohol (VII) using DIBAL. Enantioselective Simmons-Smith cyclopropanation in the presence of (+)-diethyl tartrate produced the cyclopropyl alcohols (VIII) in 80% e.e. favoring the (-)-enantiomer. This mixture was converted to the diastereomeric camphenoate esters, which were separated by preparative chromatography. The desired major isomer (IX) was then hydrolyzed to give the enantiomerically pure alcohol (X), and then oxidized to aldehyde (XI) using N-methylmorpholine-N-oxide and tetrapropylammonium perruthenate.
| 【1】 Vuligonda, V.; et al.; Enantioselective syntheses of potent retinoid X receptor ligands: Differential biological activities of individuals antipodes. J Med Chem 2001, 44, 14, 2298. |
| 【2】 Vuligonda, V.; Chandraratna, R.A. (Allergan, Inc.); 2,4-Pentadienoic acid derivs. having retinoid-like biological activity. EP 0848696; JP 1999507053; US 5675033; WO 9639374 . |
| 【3】 Chandraratna, R.A.; Vuligonda, V. (Vision Pharmaceuticals, Inc.); 2,4-Pentadienoic acid derivs. having retinoid-like biological activity. WO 9908992 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 43776 | 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene | C14H19Br | 详情 | 详情 | |
| (II) | 17922 | 2-methyl-3-butyn-2-ol; 3-Methyl butynol | 115-19-5 | C5H8O | 详情 | 详情 |
| (III) | 50525 | 2-methyl-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-3-butyn-2-ol | C19H26O | 详情 | 详情 | |
| (IV) | 50526 | 6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene | C16H20 | 详情 | 详情 | |
| (V) | 50527 | ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-2-propynoate | C19H24O2 | 详情 | 详情 | |
| (VI) | 50528 | ethyl (Z)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-2-butenoate | C20H28O2 | 详情 | 详情 | |
| (VII) | 50529 | (Z)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-2-buten-1-ol | C18H26O | 详情 | 详情 | |
| (VIII) | 50530 | [2-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)cyclopropyl]methanol | C19H28O | 详情 | 详情 | |
| (IX) | 50531 | [(1R,2S)-2-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)cyclopropyl]methyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate | C29H40O4 | 详情 | 详情 | |
| (X) | 50532 | [(1R,2S)-2-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)cyclopropyl]methanol | C19H28O | 详情 | 详情 | |
| (XI) | 50533 | (1R,2S)-2-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)cyclopropanecarbaldehyde | C19H26O | 详情 | 详情 |