(2R,3S)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (1R,2S)-2-phenylcyclohexyl ester | 128300-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (1R,2S)-2-phenylcyclohexyl ester
• 英文别名: [(1R,2S)-2-phenylcyclohexyl] (2S,3S)-3-(2-aminonaphthalen-1-yl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate
• CAS: 128300-48-1
• 化学式: C₃₂H₃₃NO₄S
• 分子量: 527.684
• InChiKey: UVEIOQQJEMZFDB-XHDJHXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-<(2-amino-1-naphthalenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (1R,2S)-2-phenylcyclohexyl ester 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 水 、 乙酸乙酯 、 xylene 为溶剂， 反应 32.0h， 生成 (+)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-naphtho<1,2-b><1,4>thiazepin-4(5H)-one
  参考文献：
  名称：

  Enantioselective synthesis of calcium channel blockers of the diltiazem group

  摘要：

  A lipase-catalyzed kinetic resolution of racemic trans-2-phenylcyclohexanol readily provides the (-)-1R,2S enantiomer. This alcohol is employed as its chloroacetate 10a in a chiral auxiliary-induced asymmetric Darzens glycidic ester condensation with p-anisaldehyde (9). Crystallization of the Darzens product affords enantiomerically pure (1R,2S)-2-phenylcyclohexyl (1R,2S)-2-(p-methoxyphenyl)glycidate (11), the structure of which was established by X-ray crystallography. The use of this glycidic ester in syntheses of diltiazem (1) and naltiazem (8), members of the diltiazem group of calcium channel blockers, provides these drug substances directly in enantiomerically pure form.

  DOI：

  10.1021/jo00029a013

文献信息

• Enantioselective synthesis of calcium channel blockers of the diltiazem group
  作者：Alan Schwartz、Pradeep B. Madan、Erno Mohacsi、Jay P. O'Brien、Louis J. Todaro、David L. Coffen

  DOI：10.1021/jo00029a013

  日期：1992.1

  A lipase-catalyzed kinetic resolution of racemic trans-2-phenylcyclohexanol readily provides the (-)-1R,2S enantiomer. This alcohol is employed as its chloroacetate 10a in a chiral auxiliary-induced asymmetric Darzens glycidic ester condensation with p-anisaldehyde (9). Crystallization of the Darzens product affords enantiomerically pure (1R,2S)-2-phenylcyclohexyl (1R,2S)-2-(p-methoxyphenyl)glycidate (11), the structure of which was established by X-ray crystallography. The use of this glycidic ester in syntheses of diltiazem (1) and naltiazem (8), members of the diltiazem group of calcium channel blockers, provides these drug substances directly in enantiomerically pure form.