2-hydroxy-3,3-dimethylcyclopentanecarboxylic acid methyl ester | 80969-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3,3-dimethylcyclopentanecarboxylic acid methyl ester
• 英文别名: Methyl 2-hydroxy-3,3-dimethylcyclopentane-1-carboxylate
• CAS: 80969-69-3
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: MJFCLBPCZMJNSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  2-hydroxy-3,3-dimethylcyclopentanecarboxylic acid methyl ester 在 氢氧化钾 、 ammonium hydroxide 、 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 1-(2-Mercapto-3,3-dimethyl-cyclopentanecarbonyl)-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors as antihypertensive agents: 1-[(2-mercaptocycloalkyl)carbonyl]-L-prolines

  摘要：

  The synthesis of 1-[(2-mercaptocyclopentyl)carbonyl]-L-prolines, 1-[(2-mercaptocyclobutyl)carbonyl]-L-prolines and related benzoyl derivatives as pure isomers is described. The abilities of all the compounds to inhibit angiotensin converting enzyme (ACE) in vitro and in vivo and to lower the systolic blood pressure in renal hypertensive dogs were determined. Three of them, namely 1-[[2-(benzoylthio)cyclopentyl]carbonyl]-L-proline (10f(R,S], 1-[(2-mercaptocyclopentyl)carbonyl]-L-proline (10g(R,S], and 1-[[2-(benzoylthio)cyclobutyl]carbonyl]-L-proline (16f(R,S], were found to be as potent as captopril in reducing blood pressure. The influence of chirality and ring size on the ACE inhibition is described.

  DOI：

  10.1021/jm00153a017
• 作为产物：
  描述：

  methyl 3,3-dimethyl-2-oxocyclopentanecarboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以79%的产率得到2-hydroxy-3,3-dimethylcyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors as antihypertensive agents: 1-[(2-mercaptocycloalkyl)carbonyl]-L-prolines

  摘要：

  The synthesis of 1-[(2-mercaptocyclopentyl)carbonyl]-L-prolines, 1-[(2-mercaptocyclobutyl)carbonyl]-L-prolines and related benzoyl derivatives as pure isomers is described. The abilities of all the compounds to inhibit angiotensin converting enzyme (ACE) in vitro and in vivo and to lower the systolic blood pressure in renal hypertensive dogs were determined. Three of them, namely 1-[[2-(benzoylthio)cyclopentyl]carbonyl]-L-proline (10f(R,S], 1-[(2-mercaptocyclopentyl)carbonyl]-L-proline (10g(R,S], and 1-[[2-(benzoylthio)cyclobutyl]carbonyl]-L-proline (16f(R,S], were found to be as potent as captopril in reducing blood pressure. The influence of chirality and ring size on the ACE inhibition is described.

  DOI：

  10.1021/jm00153a017

文献信息

• US4385062A
  申请人：——

  公开号：US4385062A

  公开（公告）日：1983-05-24
• US4496743A
  申请人：——

  公开号：US4496743A

  公开（公告）日：1985-01-29