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【结 构 式】

【分子编号】27395

【品名】2,2-dimethyl-2H-chromene-6-carbonitrile

【CA登记号】

【 分 子 式 】C12H11NO

【 分 子 量 】185.22548

【元素组成】C 77.81% H 5.99% N 7.56% O 8.64%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

1) The cyclization of 4-cyanophenol (I) with 3-chloro-3-methylbutine (II) by means of benzyltrimethylammonium hydroxide in methanol-CH2Cl2 gives 6-cyano-2,2-dimethyl-2H-benzo[b]pyran (III), which is treated with N-bromosuccinimide in DMSO to afford 6-cyano-trans-3-bromo-3,4-dihydro-2,2-dimethyl 2H benzo[b]pyran-4-ol (IV). Epoxidation of (IV) by means of NaOH in dioxane-water yields 6-cyano-3-(4-dihydro-3,4-epoxy-2,2-dimethyl-2H-benzo[b]pyran (V), which is finally treated with 4-aminobutyric acid (VI) and NaHCO3 in refluxing ethanol. 2) By reaction of epoxide (V) with 2-pyrrolidone (X) by means of NaH in DMSO.

1 Evans, J.M.; Buckingham, R.E.; Willcocks, K. (SmithKline Beecham plc); Benzopyrans. EP 0076075; JP 3014573; JP 5202034; US 4446113 .
2 Faruk, E.A. (SmithKline Beecham plc); Antihypertensive chromenes and chromans. EP 0093535; US 4510152 .
3 Castaner, J.; Mannhold, R.; BRL-34915. Drugs Fut 1986, 11, 3, 175.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 27394 Trimethylbenzylammonium Hydroxide; N,N,N-trimethyl(phenyl)methanaminium hydroxide; Triton B; Benzyltrimethylammonium hydroxide 100-85-6 C10H17NO 详情 详情
(I) 25109 4-hydroxybenzonitrile 767-00-0 C7H5NO 详情 详情
(II) 22416 3-chloro-3-methyl-1-butyne 1111-97-3 C5H7Cl 详情 详情
(III) 27395 2,2-dimethyl-2H-chromene-6-carbonitrile C12H11NO 详情 详情
(IV) 27396 3-bromo-4-hydroxy-2,2-dimethyl-6-chromanecarbonitrile C12H12BrNO2 详情 详情
(V) 12861 2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile C12H11NO2 详情 详情
(VI) 13620 4-Amino-n-butyric acid; 4-Aminobutyric acid;Piperidinic acid;Piperidic acid 56-12-2 C4H9NO2 详情 详情
(X) 27397 2-Pyrrolidinone 616-45-5 C4H7NO 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

The reaction of epoxide (V) with ammonia in ethanol gives 4-amino-6-cyano-3,4-dihydro-2,2-dimethyl-trans-2H-benzo[b]pyran-3-ol (VII), which is condensed with 4-chlorobutyryl chloride (VIII) by means of NaOH in CHCl3 yielding 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-(4-chlorobutyrylamino)-2H-benzo[blpyran 3-ol (IX). Finally, this compound is cyclized by means of NaH in THF.

1 Faruk, E.A. (SmithKline Beecham plc); Antihypertensive chromenes and chromans. EP 0093535; US 4510152 .
2 Evans, J.M.; Buckingham, R.E.; Willcocks, K. (SmithKline Beecham plc); Benzopyrans. EP 0076075; JP 3014573; JP 5202034; US 4446113 .
3 Castaner, J.; Mannhold, R.; BRL-34915. Drugs Fut 1986, 11, 3, 175.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 27394 Trimethylbenzylammonium Hydroxide; N,N,N-trimethyl(phenyl)methanaminium hydroxide; Triton B; Benzyltrimethylammonium hydroxide 100-85-6 C10H17NO 详情 详情
(I) 25109 4-hydroxybenzonitrile 767-00-0 C7H5NO 详情 详情
(II) 22416 3-chloro-3-methyl-1-butyne 1111-97-3 C5H7Cl 详情 详情
(III) 27395 2,2-dimethyl-2H-chromene-6-carbonitrile C12H11NO 详情 详情
(IV) 27396 3-bromo-4-hydroxy-2,2-dimethyl-6-chromanecarbonitrile C12H12BrNO2 详情 详情
(V) 12861 2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile C12H11NO2 详情 详情
(VII) 27398 (3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbonitrile C12H14N2O2 详情 详情
(VIII) 11265 4-Chlorobutanoyl chloride; 4-Chlorobutyric acid chloride 4635-59-0 C4H6Cl2O 详情 详情
(IX) 27399 4-chloro-N-[(3S,4R)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-4-yl]butanamide C16H19ClN2O3 详情 详情
Extended Information