((1S,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl)-acetic acid | 342652-33-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ((1S,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl)-acetic acid
• 英文别名: 2-[(1S,3R)-1-(2-methoxy-2-oxoethyl)-3-methylcyclopentyl]acetic acid
• CAS: 342652-33-9
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: RSGLEFABCXIVCD-KCJUWKMLSA-N

物化性质

• 沸点：
  321.5±15.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((1S,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl)-acetic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and in vivo evaluation of 3-substituted gababutins

  摘要：

  A range of 3-alkylated five-membered ring derivatives of Gabapentin were synthesized and several were found to have good levels of potency against the alpha 2 delta calcium subunit of a voltage-gated calcium channel. Two compounds were pro. led in in vivo models of pain and anxiety. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.089
• 作为产物：
  描述：

  ((1S,3R)-1-benzyl-3-methyl-cyclopentyl)-acetic acid methyl ester 在 sodium periodate 、 ruthenium trichloride 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 21.0h， 以87.7%的产率得到((1S,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl)-acetic acid
  参考文献：
  名称：

  Novel method for the stereoselective synthesis of cyclic amino acids

  摘要：

  该即时发明是一种合成Formula（A）的立体特异性3-取代5-成员环异构体的途径。最终产品可用作治疗癫痫、昏厥发作、运动减少、颅内疾病、神经退行性疾病、抑郁症、焦虑症、恐慌、疼痛、神经病理性疾病、肠道疾病（如肠易激综合征）、炎症尤其是关节炎、睡眠障碍、经前综合征和潮热的药剂。该发明提供了合成Gabapentin（Neurontin™）的立体选择性类似物的新途径，其化学式为（I）、（II）、（III）和（IV），其中R为C1-C10烷基或C3-C10环烷基及其药学上可接受的盐。

  公开号：

  US20060084825A1

文献信息

• Method for the stereoselective synthesis of cyclic amino acids
  申请人：——

  公开号：US20030069438A1

  公开（公告）日：2003-04-10

  1 The instant invention is a route to stereospecific 3-substituted 5-membered ring isomers of Formula (A). The final products are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), inflammation especially arthritis, sleep disorders, premenstrual syndrome, and hot flashes. The invention provides novel routes to synthesize stereoselectively analogs of gabapentin (Neurontin™) of Formulas (I), (II), (III) and (IV) wherein R is C 1 -C 10 alkyl or C 3 -C 10 cycloalkyl and pharmaceutically acceptable salts thereof.

  该发明是一种合成具有立体选择性的Formula (A)中的3-取代5-成员环异构体的途径。最终产物可用作治疗癫痫、晕厥、运动减退、颅内疾病、神经退行性疾病、抑郁症、焦虑症、惊恐症、疼痛、神经病理性疾病、肠道疾病如肠易激综合征（IBS）、炎症特别是关节炎、睡眠障碍、经前综合症和潮热的药物。该发明提供了新的途径，以立体选择性地合成Formula (I)、(II)、(III)和(IV)中的gabapentin（Neurontin™）的类似物，其中R为C1-C10烷基或C3-C10环烷基和其药学上可接受的盐。
• METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CYCLIC AMINO ACIDS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1237847A1

  公开（公告）日：2002-09-11
• US6864390B2
  申请人：——

  公开号：US6864390B2

  公开（公告）日：2005-03-08
• [EN] METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CYCLIC AMINO ACIDS<br/>[FR] METHODE DE SYNTHESE STEREOSELECTIVE D'ACIDES AMINES CYCLIQUES
  申请人：WARNER LAMBERT CO

  公开号：WO2001042190A1

  公开（公告）日：2001-06-14

  The instant invention is a route to stereospecific 3-substituted 5-membered ring isomers of Formula (A). The final products are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), inflammation especially arthritis, sleep disorders, premenstrual syndrome, and hot flashes. The invention provides novel routes to synthesize stereoselectively analogs of gabapentin (Neurontin®) of Formulas (I), (II), (III) and (IV) wherein R is C1-C10 alkyl or C3-C10 cycloalkyl and pharmaceutically acceptable salts thereof.
• Synthesis and in vivo evaluation of 3-substituted gababutins
  作者：David C. Blakemore、Justin S. Bryans、Pauline Carnell、Nicola E.A. Chessum、Mark J. Field、Natasha Kinsella、Jack K. Kinsora、Simon A. Osborne、Sophie C. Williams

  DOI：10.1016/j.bmcl.2009.10.089

  日期：2010.1

  A range of 3-alkylated five-membered ring derivatives of Gabapentin were synthesized and several were found to have good levels of potency against the alpha 2 delta calcium subunit of a voltage-gated calcium channel. Two compounds were pro. led in in vivo models of pain and anxiety. (C) 2009 Elsevier Ltd. All rights reserved.