(S)-6-chloro-2,3-dihydro-4H-1-benzopyran-3-carboxylic acid | 164265-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-6-chloro-2,3-dihydro-4H-1-benzopyran-3-carboxylic acid
• 英文别名: (-)-6-chloro-2,3-dihydro-4H-1-benzopyran-3-carboxylic acid；(3S)-6-Chlorochromane-3-carboxylic acid；(3S)-6-chloro-3,4-dihydro-2H-chromene-3-carboxylic acid
• CAS: 164265-09-2
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: UTLYAMDODADLNQ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-6-chloro-2,3-dihydro-4H-1-benzopyran-3-carboxylic acid 在 lithium aluminium tetrahydride 、 三溴化磷 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (S)-(+)-6-chloro-3-methyl-2,3-dihydro-4H-1-benzopyran
  参考文献：
  名称：

  6-Chloro-2,3-dihydro-4H-1-benzopyran carboxylic acids: Synthesis, optical resolution and absolute configuration

  摘要：

  6-Chloro-2,3-dihydro-4H-1-benzopyran-2-carboxylic acid, a rigid analogue of clofibric acid, the active metabolite of the antilipidemic drug clofibrate, has been prepared together with two isomers, 6-chloro-2,3-dihydro-4H-1-benzopyran-3- and 4-carboxylic acids. The three acids have been resolved into their optical antipodes and the absolute configuration established by chemical correlation.

  DOI：

  10.1016/0957-4166(95)00111-2
• 作为产物：
  描述：

  6-氯-2H-苯并吡喃-3-甲醛 在 sodium hydroxide 、 sodium amalgam 、 silver(l) oxide 作用下， 以 乙醇 为溶剂， 反应 24.75h， 生成 (S)-6-chloro-2,3-dihydro-4H-1-benzopyran-3-carboxylic acid
  参考文献：
  名称：

  6-Chloro-2,3-dihydro-4H-1-benzopyran carboxylic acids: Synthesis, optical resolution and absolute configuration

  摘要：

  6-Chloro-2,3-dihydro-4H-1-benzopyran-2-carboxylic acid, a rigid analogue of clofibric acid, the active metabolite of the antilipidemic drug clofibrate, has been prepared together with two isomers, 6-chloro-2,3-dihydro-4H-1-benzopyran-3- and 4-carboxylic acids. The three acids have been resolved into their optical antipodes and the absolute configuration established by chemical correlation.

  DOI：

  10.1016/0957-4166(95)00111-2

文献信息

• Lipase-mediated kinetic resolution of rigid clofibrate analogues with lipid-modifying activity
  作者：Savina Ferorelli、Carlo Franchini、Fulvio Loiodice、Maria Grazia Perrone、Antonio Scilimati、Maria Stefania Sinicropi、Paolo Tortorella

  DOI：10.1016/s0957-4166(01)00119-7

  日期：2001.4

  workable reaction rates. Enantiomerically pure (R)- and (S)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acids were obtained by fractional crystallisation of the diastereomeric salts of the corresponding racemic acid with (+)- and (−)-amphetamine from ethanol; the absolute configuration of the products were established by chemical correlation.

  （±）-5-氯-2,3-二氢-1-苯并呋喃-2-羧酸，（±）甲酯的脂肪酶催化的动力学拆分-6-氯-2,3-二氢-4- ħ -氯贝贝特的刚性类似物1-苯并吡喃-2-羧酸和（±）-6-氯-2,3-二氢-4 H -1-苯并吡喃-3-羧酸具有中等至中等对映选择性（E = 1.0–4.8），对映体过量高达86％，反应速率可行。对映体纯的（R）-和（S通过将相应的外消旋酸的非对映异构盐与（+）-和（-）-苯异丙胺从乙醇中分步结晶得到）-5-氯-2,3-二氢-1-苯并呋喃-2-羧酸。产品的绝对构型是通过化学相关性确定的。