4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester -Drug Synthesis Database

【结构式】

【分子编号】53342

【品名】4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester

【CA登记号】73183-34-3

【分子式】C₁₂H₂₄B₂O₄

【分子量】253.94216

【元素组成】C 56.76% H 9.53% B 8.51% O 25.2%

与该中间体有关的原料药合成路线共 8 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6 合成路线7 合成路线8

合成路线1

该中间体在本合成路线中的序号：(VI)

The borinated tyrosine intermediate (VII) has been obtained as follows: The esterification of L-tyrosine (I) with SOCl2 and methanol gives the methyl ester (II), which is N-protected with Cbz-Cl and K2CO3 to yield the carbamate (III). The O-protection of (III) with benzyl bromide and Cs2CO3 affords the benzyl ether (IV), which is iodinated with I2 and Ag2SO4 to provide the 3-iodotyrosine derivative (V). Finally, the borylation of (V) by means of pinacolatodiborane (VI) catalyzed by PdCl2[bis(diphenylphosphanyl)ferrocene] (PdCl2(dppf)) gives rise to the target tyrosine intermediate (VII).

参考文献中间体

合成目标

【1】 Lin, S.N.; Danishefsky, S.J.; The total synthesis of proteasome inhibitors TMC-95A and TMC-95B: Discovery of a new method to generate cis-propenyl amides. Angew Chem. Int Ed 2002, 41, 3, 512.

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)	48794	(S)-(-)-Tyrosine; (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)-L-alanine; L-(-)-Tyrosine; L-3-(4-Hydroxyphenyl)alanine; L-4-Hydroxy-17O-phenylalanine; L-beta-(p-Hydroxyphenyl)alanine; L-Hydroxy Phenyl Alanine; L-tyrosine	60-18-4	C₉H₁₁NO₃	详情	详情
(II)	21431	methyl (2S)-2-amino-3-(4-hydroxyphenyl)propanoate	1080-06-4	C₁₀H₁₃NO₃	详情	详情
(III)	53339	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate	n/a	C₁₈H₁₉NO₅	详情	详情
(IV)	53340	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(benzyloxy)phenyl]propanoate	n/a	C₂₅H₂₅NO₅	详情	详情
(V)	53341	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(benzyloxy)-3-iodophenyl]propanoate	n/a	C₂₅H₂₄INO₅	详情	详情
(VI)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情
(VII)	53343	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate	n/a	C₃₁H₃₆BNO₇	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

参考文献中间体

合成目标

【1】 Lin, S.N.; Danishefsky, S.J.; The total synthesis of proteasome inhibitors TMC-95A and TMC-95B: Discovery of a new method to generate cis-propenyl amides. Angew Chem. Int Ed 2002, 41, 3, 512.

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)	48794	(S)-(-)-Tyrosine; (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid; 3-(4-Hydroxyphenyl)-L-alanine; L-(-)-Tyrosine; L-3-(4-Hydroxyphenyl)alanine; L-4-Hydroxy-17O-phenylalanine; L-beta-(p-Hydroxyphenyl)alanine; L-Hydroxy Phenyl Alanine; L-tyrosine	60-18-4	C₉H₁₁NO₃	详情	详情
(II)	21431	methyl (2S)-2-amino-3-(4-hydroxyphenyl)propanoate	1080-06-4	C₁₀H₁₃NO₃	详情	详情
(III)	53339	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate	n/a	C₁₈H₁₉NO₅	详情	详情
(IV)	53340	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(benzyloxy)phenyl]propanoate	n/a	C₂₅H₂₅NO₅	详情	详情
(V)	53341	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(benzyloxy)-3-iodophenyl]propanoate	n/a	C₂₅H₂₄INO₅	详情	详情
(VI)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情
(VII)	53343	methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate	n/a	C₃₁H₃₆BNO₇	详情	详情

合成路线3

该中间体在本合成路线中的序号：(IV)

Addition of methylmagnesium bromide to methyl 2-amino-5-bromobenzoate (I) provides the tertiary alcohol (II). Subsequent ring closure of the amino carbinol (II) with acetaldehyde leads to the benzoxazine (III). Treatment of the bromobenzoxazine (III) with bis(pinacolato)diboron (IV) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride furnishes the aryl borate (V). This is finally subjected to Suzuki coupling with 5-bromo-2-thiophenecarbonitrile (VI) to produce the title benzoxazinyl thiophene derivative.

参考文献中间体

合成目标

【1】 Zhang, P.; et al.; Potent nonsteroidal progesterone receptor agonists: Synthesis and SAR study of 6-aryl benzoxazines. Bioorg Med Chem Lett 2002, 12, 5, 787.
【2】 Jones, T.K.; Zhi, L.; Tegley, C.M.; Fensome, A.; Zhang, P.; Terefenko, E.A.; Marschke, K.B. (Ligand Pharmaceuticals, Inc.; Wyeth); Quinazolinone and benzoxazine derivs. as progesterone receptor modulators. EP 1175404; WO 0066560 .
【3】 Jones, T.K.; Zhi, L.; Tegley, C.M.; Marschke, K.B.; Grubb, G.S. (Ligand Pharmaceuticals, Inc.; Wyeth); Contraceptive compsns. containing quinazolinone and benzoxazine derivs.. WO 0066164; WO 0066165 .

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)	58335	methyl 2-amino-5-bromobenzoate		C₈H₈BrNO₂	详情	详情
(II)	58336	2-(2-amino-5-bromophenyl)-2-propanol		C₉H₁₂BrNO	详情	详情
(III)	58337	6-bromo-2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazine		C₁₁H₁₄BrNO	详情	详情
(IV)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情
(V)	58338	2,4,4-trimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dihydro-2H-3,1-benzoxazine		C₁₇H₂₆BNO₃	详情	详情
(VI)	58339	4-bromo-2-thiophenecarbonitrile		C₅H₂BrNS	详情	详情

合成路线4

该中间体在本合成路线中的序号：(XII)

Cyclization of morpholine-4-carboximidamide hydrobromide (I) with diethyl malonate (II) by means of naoEt in refluxing EtoH gives 2-(morpholin-4-yl)pyrimidine-4,6-diol (III), which by chlorination with PoCl3 at 120 °C affords 4,6-dichloro-2-(morpholin-4-yl)pyrimidine (IV). nucleophilic substitution of the dichloropyrimidine (IV) with morpholine (V) in the presence of Et3n in refluxing N-methyl-2-pyrrolidone provides 2,4-di(morpholin-4-yl)-6-chloropyrimidine (VI) . Alternatively, dimorpholinopyrimidine (VI) is prepared by reaction of 2,4,6-trichloropyrimidine (VII) with morpholine (V) in THF, followed by chromatographic separation . Finally, chloropyrimidine derivative (VI) is submitted to a Suzuki cross-coupling reaction with boronate ester (VIII) in the presence of Pd(dppf)2Cl2·CH2Cl2 or Pd(dppf)2Cl2 and na2Co3 in 1,2-dimethoxyethane at 90-95 °C .
Alternatively, iodination of chloride (VI) with HI and naI yields the corresponding iodide (IX) , which is also coupled with boronate (VIII) in the presence of Pd(dppf)Cl2·CH2Cl2 and K2Co3 in 1,4-dioxane/H2o at 100 °C .
Boronate ester (VIII) is obtained by bromination of 4-(trifluoromethyl) pyridin-2-amine (X) with nBS in CHCl3 or CH2Cl2 to afford 5-bromo-4-(trifluoromethyl)pyrimidin-2-amine (XI), which is finally condensed with bis(pinacolato)diboron (XII) in the presence of Pd(dppf)2Cl2·CH2Cl2 and KoAc in refluxing dioxane or DMSO .

参考文献中间体

合成目标

【1】 Pick, T., Barsanti, P., Iwanowicz, E. et al. (novartis AG). Pyrimidine derivatives used as PI-3 kinase inhibitors. EP 1984350, EP 2261223, JP 200952764, US 2010249126, US 8217035, US 2012225859, Wo 2007084786.
【2】 Burger, M.T., Pecchi, S., Wagman, A. et al. Discovery of BKM120, a pan class I PI3 kinase inhibitor in phase I/II clinical trials. 240th ACS natl Meet (Aug 22-26, Boston) 2010, Abst MEDI 489.
【3】 Vu, A.T., Morris, J. Malhotra, S.V. Efficient and improved synthesis of a PI3K inhibitor anticancer agent. 241st ACS natl Meet (March 27-31, Anaheim) 2011, Abst oRGn 115.

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)	67957	morpholine-4-carboximidamide hydrobromide		C₅H₁₁N₃O.HBr	详情	详情
(II)	16829	Diethyl malonate	105-53-3	C₇H₁₂O₄	详情	详情
(III)	67958	2-morpholinopyrimidine-4,6-diol		C₈H₁₁N₃O₃	详情	详情
(IV)	67959	4,6-dichloro-2-(morpholin-4-yl)pyrimidine	10397-13-4	C₈H₉Cl₂N₃O	详情	详情
(V)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(VI)	67960	4,4'-(6-chloropyrimidine-2,4-diyl)dimorpholine		C₁₂H₁₇ClN₄O₂	详情	详情
(VII)	43734	2,4,6-trichloropyrimidine	3764-01-0	C₄HCl₃N₂	详情	详情
(VIII)	67961	5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyridin-2-amine		C₁₂H₁₆BF₃N₂O₂	详情	详情
(IX)	67962	4,4'-(6-iodopyrimidine-2,4-diyl)dimorpholine		C₁₂H₁₇IN₄O₂	详情	详情
(X)	67963	4-(trifluoromethyl)pyridin-2-amine	106447-97-6	C₆H₅F₃N₂	详情	详情
(XI)	67964	5-bromo-4-(trifluoromethyl)pyridin-2-amine		C₆H₄BrF₃N₂	详情	详情
(XII)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情

合成路线5

该中间体在本合成路线中的序号：(XII)

Bromination of 2-amino-4-(trifluoromethyl)pyridine (X) with nBS in THF affords 2-amino-5-bromo-4-(trifluoromethyl)pyridine (XI), which by N-acetylation with Ac2o and DMAP in EtoAc yields the corresponding acetamide (XIII), which by sequential metalation with BuLi in THF, borylation with (i-Pro)3B and hydrolysis with HCl affords the boronic acid (XIV). Suzuki cross-coupling of boronic acid (XIV) with 4-chloro-2,6-di(morpholin-4-yl)pyrimidine (VI) in the presence of Pd(PPh3)4 and K2Co3 in DME at 70 °C results in N-[4-trifluoro methyl-5-(2,6-dimorpholinopyrimidin-4-yl)pyridin-2-yl]acetamide (XV), which is finally deacetylated by treatment with HCl .
. Alternatively, Miyaura borylation of 4-chloro-2,6-di(morpholin-4-yl)pyrimidine (VI) with bis(pinacolato)diboron (XII) by means of Pd2dba3, KoAc and Cy3P in acetonitrile gives boronate ester (XVI), which is finally submitted to Suzuki cross-coupling with 2-amino-5-bromo-4-(trifluoromethyl)pyridine (XI) in the presence of Pd(dppf)Cl2 and Cs2Co3 in THF .

参考文献中间体

合成目标

【1】 Calienni, J.V., De La Cruz, M., Flubacher, D. et al. (novartis AG). Manufacturing process for pyrimidine derivatives. Wo 2012044727.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	67960	4,4'-(6-chloropyrimidine-2,4-diyl)dimorpholine		C₁₂H₁₇ClN₄O₂	详情	详情
(X)	67963	4-(trifluoromethyl)pyridin-2-amine	106447-97-6	C₆H₅F₃N₂	详情	详情
(XI)	67964	5-bromo-4-(trifluoromethyl)pyridin-2-amine		C₆H₄BrF₃N₂	详情	详情
(XI)	67964	5-bromo-4-(trifluoromethyl)pyridin-2-amine		C₆H₄BrF₃N₂	详情	详情
(XII)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情
(XIII)	67965	N-(5-bromo-4-(trifluoromethyl)pyridin-2-yl)acetamide		C₈H₆BrF₃N₂O	详情	详情
(XIV)	67966	(6-acetamido-4-(trifluoromethyl)pyridin-3-yl)boronic acid		C₈H₈BF₃N₂O₃	详情	详情
(XV)	67967	N-[4-trifluoro methyl-5-(2,6-dimorpholinopyrimidin-4-yl)pyridin-2-yl]acetamide		C₂₀H₂₃F₃N₆O₃	详情	详情
(XVI)	67968	4,4'-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2,4-diyl)dimorpholine		C₁₈H₂₉BN₄O₄	详情	详情

合成路线6

该中间体在本合成路线中的序号：(III)

Reaction of 5-bromo-3-[1(R)-(2,6-dichloro-3-fluorophenyl)ethyl]-pyridin-2-amine (I) with Boc2O by means of DMAP in DMF gives the protected aniline (II), which is condensed with bis(pinacolato)-diboron (III) by means of a Pd catalyst and KOAc in DMSO to yield the N-protected boronic ester (IV). Deprotection of the amino group of compound (IV) by means of HCl in dioxane/dichloromethane affords the boronic ester (V), which is condensed with 1-(1-Boc-piperidin-4-yl)-4-bromo-1H-pyrazole (VI) by means of PdCl2(PPh3)2 and Na2CO3 in hot DME/water to provide the adduct (VII). Finally, this compound is N-deprotected by means of HCl in dioxane/dichloromethane, as before .

参考文献中间体

合成目标

【1】 Cui, J.J., Funk, L.A., Jia, L. et al. (Pfizer, Inc.; Agouron Pharmaceuticals, Inc.). Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors. EP 1786785, JP 2008510790, US 2006046991, WO 2006021884.
【2】 Cui, J.J., Funk, L.A., Jia, L. et al. (Pfizer, Inc.). Pyrazole-substituted aminoheteroaryl compounds as protein kinase inhibitors. EP 1784396, JP 2008510788, WO 2006021881.

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)	68698	5-bromo-3-[1(R)-(2,6-dichloro-3-fluorophenyl)ethyl]-pyridin-2-amine;(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine		C₁₃H₁₀BrCl₂FN₂O	详情	详情
(II)	68697			C₂₃H₂₆BrCl₂FN₂O₅	详情	详情
(III)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情
(IV)	68696			C₂₉H₃₈BCl₂FN₂O₇	详情	详情
(V)	68695	(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine		C₁₉H₂₂BCl₂FN₂O₃	详情	详情
(VI)	68694	1-(1-Boc-piperidin-4-yl)-4-bromo-1H-pyrazole;4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylicacid tert-butyl ester	877399-50-3	C₁₃H₂₀BrN₃O₂	详情	详情
(VII)	68693	(R)-tert-butyl 4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate		C₂₆H₃₀Cl₂FN₅O₃	详情	详情

合成路线7

该中间体在本合成路线中的序号：(XXVII)

In one method, oxidation of 4-chloro-2-nitrotoluene (XXIV) with NaIO4 in the presence of DMFA in DMF at 135 °C yields 4-chloro-2-nitrobenzaldehyde (XXV). Reduction of the nitro group in compound (XXV) with Fe and HCl in EtOH/H2O, followed by Friedländer condensation of the resulting aminoaldehyde with acetophenone (XIV) using KOH at reflux gives 7-chloro-2-phenylquinoline (XXVI). Miyaura borylation of chloroquinoline (XXVI) with bis(pinacolato)diboron (XXVII) in the presence of 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride [IPr·HCl], Pd(OAc)2 and KOAc in refluxing THF furnishes boronate ester (XI).
In another method, arylation of 7-quinolinol (XXVIII) using phenyl lithium in THF, optionally after protection of the hydroxyl group with TBDMSCl in the presence of DMAP and Et3N in CH2Cl2, leads to 2-phenyl-7-quinolinol (XXIX). Quinolinol (XXIX) is then activated by Tf2O in pyr/CH2Cl2 to produce the aryl triflate (XXX), which condenses with bis(pinacolato)diboron (XXVII) in the presence of PdCl2(dppf) CH2Cl2, dppf and KOAc in 1,4-dioxane to afford the dioxaborolane derivative (XI) .

参考文献中间体

合成目标

【1】 Arnold, L.D., Cesario, C., Coate, H. et al. (OSI Pharmaceuticals, Inc.). 6,6-Bicyclic ring substituted heterobicyclic protein kinase inhibitors. EP 1740591, EP 2168968, EP 2305682, EP 2308879, JP 2007531754, JP 2009197013, US 200635031, WO 005097800.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	68928	2-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline		C₂₁H₂₂BNO₂	详情	详情
(XIV)	10317	Acetophenone	98-86-2	C₈H₈O	详情	详情
(XXIV)	41485	4-chloro-1-methyl-2-nitrobenzene；4-chloro-2-nitrotoluene;4-chloro-1-methyl-2-nitro-benzene	89-59-8	C₇H₆ClNO₂	详情	详情
(XXV)	68938	4-chloro-2-nitrobenzaldehyde;2-Nitro-4-chlorobenzaldehyde	5551-11-1	C₇H₄ClNO₃	详情	详情
(XXVI)	68939	7-chloro-2-phenylquinoline		C₁₅H₁₀ClN	详情	详情
(XXVII)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情
(XXVIII)	68940	quinolin-7-ol		C₉H₇NO	详情	详情
(XXIX)	68941	2-phenyl-7-quinolinol;2-phenylquinolin-7-ol		C₁₅H₁₁NO	详情	详情
(XXX)	68942	2-phenylquinolin-7-yl trifluoromethanesulfonate		C₁₆H₁₀F₃NO₃S	详情	详情

合成路线8

该中间体在本合成路线中的序号：(XXII)

Intermediates (X) and (XII) are prepared by Wittig olefination of cyclopentylcarboxaldehyde (VII) with (triphenylphosphoranylidene)-acetaldehyde (XIX) in benzene at 80 °C, followed by preparative HPLC separation to yield (E)-3-cyclopentylacrylaldehyde (X), which upon asymmetric aza-Michael reaction with 4-bromopyrazole (XIIIa) by means of a chiral catalyst and p-NBA in THF/H2O gives the Michael adduct (XX). Then, aldehyde (XX) is treated with NH4OH and I2 in 1,4-dioxane/H2O to give nitrile (XXI), which is finally reacted with bis(pinacolato)diboron (XXII) in the presence of Pd(PPh3)4 and KOAc in 1,4-dioxane at 120 °C .

参考文献中间体

合成目标

【1】 Lin, Q., Meloni, D., Pan, Y. et al. Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-Michael reaction. Org Lett 2009, 11(9): 1999-2002.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIIIa)	69178	4-iodopyrazole;4-Iodo-1H-pyrazole	3469-69-0	C₃H₃IN₂	详情	详情
(B)	69184	2-(bis(3,5-bis(trifluoromethyl)phenyl)((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine		C₂₇H₂₉F₁₂NOSi	详情	详情
(VII)	69171	cyclopentylcarboxaldehyde；Cyclopentanecarbaldehyde;Cyclopentanealdehyde;Cyclopentyl aldehyde;Cyclopentylformaldehyde;Formylcyclopentane	872-53-7	C₆H₁₀O	详情	详情
(X)	69176	(E)-3-cyclopentylacrylaldehyde		C₈H₁₂O	详情	详情
(XII)	69177	(S)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile		C₁₇H₂₆BN₃O₂	详情	详情
(XIX)	69183	Triphenyl phosphine;Triphenyl phosphorous;(triphenylphosphoranylidene)-acetaldehyde	2136-75-6	C₁₈H₁₅PO	详情	详情
(XX)	69185	(R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanal		C₁₁H₁₅BrN₂O	详情	详情
(XXI)	69186	(R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile		C₁₁H₁₄BrN₃	详情	详情
(XXII)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情

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