(4-chloro-3-methylphenyl) (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (4-chloro-3-methylphenyl) (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylate
• 化学式: C₁₇H₁₅ClO₄
• 分子量: 318.757
• InChiKey: LAUPJFHHHDUNNR-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (4-chloro-3-methylphenyl) (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylate 生成 (4-chloro-3-methylphenyl) (2R,3S)-3-(4-methoxyphenyl)oxirane-2-carboxylate
  参考文献：
  名称：

  First practical resolution of a 3-(4-methoxyphenyl)glycidic acid ester by preferential crystallization and synthesis of diltiazem

  摘要：

  Among the various esters of 3-(4-methoxyphenyl)glycidic acid, 4-chloro-3-methylphenyl ester (+/-)-3 was found to exist as a conglomerate, and could be alternately resolved into (+)- and (-)-3 of >98% ee by a preferential crystallization procedure. Furthermore, a 1,5-benzothiazepine derivative, (+)-6, a significant intermediate of diltiazem, was prepared in one pot in 76% overall yield through the treatment of enantiomerically pure (-)-3 with 2-aminothiophenol followed by a ring closing reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00148-7
• 作为产物：
  描述：

  4-氯-3-甲基苯酚 在 三乙胺 、 2-chloro-1-methylpyridinium sulfate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (4-chloro-3-methylphenyl) (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylate
  参考文献：
  名称：

  First practical resolution of a 3-(4-methoxyphenyl)glycidic acid ester by preferential crystallization and synthesis of diltiazem

  摘要：

  Among the various esters of 3-(4-methoxyphenyl)glycidic acid, 4-chloro-3-methylphenyl ester (+/-)-3 was found to exist as a conglomerate, and could be alternately resolved into (+)- and (-)-3 of >98% ee by a preferential crystallization procedure. Furthermore, a 1,5-benzothiazepine derivative, (+)-6, a significant intermediate of diltiazem, was prepared in one pot in 76% overall yield through the treatment of enantiomerically pure (-)-3 with 2-aminothiophenol followed by a ring closing reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00148-7

文献信息

• First practical resolution of a 3-(4-methoxyphenyl)glycidic acid ester by preferential crystallization and synthesis of diltiazem
  作者：Shin-ichi Yamada、Katsuji Morimatsu、Ryuzo Yoshioka、Yasuhiko Ozaki、Hiroyasu Seko

  DOI：10.1016/s0957-4166(98)00148-7

  日期：1998.5

  Among the various esters of 3-(4-methoxyphenyl)glycidic acid, 4-chloro-3-methylphenyl ester (+/-)-3 was found to exist as a conglomerate, and could be alternately resolved into (+)- and (-)-3 of >98% ee by a preferential crystallization procedure. Furthermore, a 1,5-benzothiazepine derivative, (+)-6, a significant intermediate of diltiazem, was prepared in one pot in 76% overall yield through the treatment of enantiomerically pure (-)-3 with 2-aminothiophenol followed by a ring closing reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.