(4R,5R)-N-t-butoxycarbonyl-4,5-methano-2-pyrrolidone | 1310363-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4R,5R)-N-t-butoxycarbonyl-4,5-methano-2-pyrrolidone
• 英文别名: (1R,5R)-3-oxo-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane；rac-tert-butyl(1R,5R)-3-oxo-2-azabicyclo[3.1.0]hexane-2-carboxylate,cis；tert-butyl (1R,5R)-3-oxo-2-azabicyclo[3.1.0]hexane-2-carboxylate
• CAS: 1310363-30-4
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: APRHZCZIWPERLL-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-N-t-butoxycarbonyl-4,5-methano-2-pyrrolidone 在 盐酸 作用下， 以 水 为溶剂， 反应 10.0h， 以40%的产率得到(1R,2R)-cis-2-amino-1-(carboxymethyl)cyclopropane hydrochloride
  参考文献：
  名称：

  Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

  摘要：

  A series of cyclopropane-based conformationally restricted gamma-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4-methano analogs IIa and IIb and their enantiomers ent-IIa and ent-Iib, were synthesized from the chiral cyclopropane units Type-a and Type-b that we developed. These analogs were systematically evaluated with four GABA transporter (GAT) subtypes. The trans-3,4-methano analog IIa had inhibitory effects on GAT3 (IC50 = 23.9 mu M) and betaine-GABA transporter1 (5.48 mu M), indicating its potential as an effective lead compound for the development of potent GAT inhibitors due to its hydrophilic and low molecular weight properties and excellent ligand efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.063
• 作为产物：
  描述：

  tert-butyl N-[(1R,2R)-2-(2-hydroxyethyl)cyclopropyl]carbamate 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 以72%的产率得到(4R,5R)-N-t-butoxycarbonyl-4,5-methano-2-pyrrolidone
  参考文献：
  名称：

  Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

  摘要：

  A series of cyclopropane-based conformationally restricted gamma-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4-methano analogs IIa and IIb and their enantiomers ent-IIa and ent-Iib, were synthesized from the chiral cyclopropane units Type-a and Type-b that we developed. These analogs were systematically evaluated with four GABA transporter (GAT) subtypes. The trans-3,4-methano analog IIa had inhibitory effects on GAT3 (IC50 = 23.9 mu M) and betaine-GABA transporter1 (5.48 mu M), indicating its potential as an effective lead compound for the development of potent GAT inhibitors due to its hydrophilic and low molecular weight properties and excellent ligand efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.063

文献信息

• A scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
  作者：Gan Wang、Clint A. James、Nicholas A. Meanwell、Lawrence G. Hamann、Makonen Belema

  DOI：10.1016/j.tetlet.2013.09.114

  日期：2013.12

  A stereoselective and scalable synthesis of (1R,35,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (3a) is described. Key to the success of the devised route was the realization that the stereoselectivity of a cyclopropanation step could be controlled by the composition of the functional group at C-alpha. (C) 2013 Elsevier Ltd. All rights reserved.