(2R,3S)-3-(4-methoxyphenyl)oxirane-2-carboxylic acid (1R,2S)-2-phenylcyclohexyl ester | 128232-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3S)-3-(4-methoxyphenyl)oxirane-2-carboxylic acid (1R,2S)-2-phenylcyclohexyl ester
• 英文别名: (2R,3S)-3-(4-methoxyphenyl)oxirane carboxylic acid (1R,2S)-2-phenylcyclohexyl ester；[(1R,2S)-2-phenylcyclohexyl] (2R,3S)-3-(4-methoxyphenyl)oxirane-2-carboxylate
• CAS: 128232-03-1
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: SSWJMRVXPAQURI-JSXRDJHFSA-N

物化性质

• 沸点：
  484.4±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(4-methoxyphenyl)oxirane-2-carboxylic acid (1R,2S)-2-phenylcyclohexyl ester 、 2-氨基苯硫醇 以 甲苯 为溶剂， 以81%的产率得到(2S,3S)-3-(2-Aminophenyl)thio-2-hydroxy3-(4-methoxybenzene) Propanoic Acid (1R,2S)-2-Phenylcyclohexyl Ester
  参考文献：
  名称：

  Glycidic acid ester and process of preparation

  摘要：

  一种制备化合物的方法，其化学式为##STR1##其中R.sub.1和R.sub.2各自独立地为氢、1至4个碳原子的烷基、1至4个碳原子的烷氧基、卤素、三氟甲基或硝基；或R.sub.1和R.sub.2与它们连接的苯环一起为萘，Ar为p-低烷氧基苯基。包括将##STR2##其中R.sub.1和R.sub.2如上所述与化合物##STR3##其中Ar如上所述，在芳香有机化合物中反应。本发明所形成的中间体在噻吩并[4(5H)-酮]的生产中是有用的，这些中间体作为钙通道阻滞剂具有活性，因此可用作降低血压的药物和治疗缺血的药物。

  公开号：

  US05008411A1
• 作为产物：
  描述：

  (1R,2S)-trans-2-phenylcyclohexanol 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2R,3S)-3-(4-methoxyphenyl)oxirane-2-carboxylic acid (1R,2S)-2-phenylcyclohexyl ester
  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.
• Glycidic acid ester and process of preparation
  申请人：Hoffmann-La Roche Inc.

  公开号：US05008411A1

  公开（公告）日：1991-04-16

  A process for the preparing a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trifluoromethyl or nitro; or R.sub.1 and R.sub.2 taken together with the benzene ring to which they are attached are naphthalene, and Ar is p-lower alkoxy phenyl. which comprises reacting ##STR2## wherein R.sub.1 and R.sub.2 are as described above with the compound of the formula ##STR3## wherein Ar is as described above, in an aromatic organic compound. The intermediates formed by the process of the invention are useful in the production of thiazepin-4(5H)-ones which have activity as calcium channel blockers and accordingly are useful as agents for lowering blood pressure and agents for treating ischemia.

  一种制备化合物的方法，其化学式为##STR1##其中R.sub.1和R.sub.2各自独立地为氢、1至4个碳原子的烷基、1至4个碳原子的烷氧基、卤素、三氟甲基或硝基；或R.sub.1和R.sub.2与它们连接的苯环一起为萘，Ar为p-低烷氧基苯基。包括将##STR2##其中R.sub.1和R.sub.2如上所述与化合物##STR3##其中Ar如上所述，在芳香有机化合物中反应。本发明所形成的中间体在噻吩并[4(5H)-酮]的生产中是有用的，这些中间体作为钙通道阻滞剂具有活性，因此可用作降低血压的药物和治疗缺血的药物。