(1S,2R)-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2R)-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane
• 英文别名: 2-{(1S,2R)-[(tert-butoxycarbonyl)amino]cyclopropyl}acetic acid；2-[(1S,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropyl]acetic acid
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: INXYYFYPMHZEHG-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane 在 盐酸 、 水 作用下， 反应 0.58h， 以76%的产率得到(1S,2R)-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：

  (1S,2R)-trans-1-(2-benzyloxy)ethyl-2-carboxycyclopropane 在 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 氢气 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 (1S,2R)-2-(t-buthoxycarbonyl)amino-1-(carboxymethyl)cyclopropane
  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

• ——
  作者：Markus Kordes、Harald Winsel、Armin de Meijere

  DOI：10.1002/1099-0690(200009)2000:18<3235::aid-ejoc3235>3.0.co;2-7

  日期：2000.9

  Our recently reported titanium-mediated transformation of N,N-dialkylcarboxamides to cyclopropylamines has been applied to N,N-dibenzyl-2-benzyloxyacetamide using a variety of alkylmagnesium bromides to yield 1-(benzyloxymethyl)-1-(dibenzylamino)cyclopropane (15a, 48%) and 2-substituted analogs 15b−f (33−48%). These have been transformed in just a few steps into N-Boc-protected methyl esters of 1-

  我们最近报道的钛介导的N，N-二烷基羧酰胺向环丙胺的转化已使用各种烷基溴化镁应用于N，N-二苄基-2-苄氧基乙酰胺，以生成1-（苄氧基甲基）-1-（二苄氨基）环丙烷（15a，48％）和2取代的类似物15b-f（33-48％）。这些已转化在短短步入Ñ 1-氨基环丙烷羧酸（-Boc保护的甲酯1整体，29％），coronamic酸（2，35％）和norcoronamic酸（21％），2,3-甲基谷氨酸（21g，19％）和2,3-甲基鸟氨酸（21l，占12％）。类似地，3,4-亚甲基- γ氨基丁酸（相应的衍生物26，23％）和4-螺环丙烷-γ丁内酰胺（32，44％）已被合成。
• Stereoselective preparation of β,γ-methano-GABA derivatives
  作者：David J. Aitken、Ludovic Drouin、Sarah Goretta、Régis Guillot、Jean Ollivier、Marco Spiga

  DOI：10.1039/c1ob06095c

  日期：——

  Meijere reaction between an unsaturated Grignard reagent and a chiral amide takes place with a high trans stereoselectivity and provides a convenient access to non-racemic trans cyclopropylamines. These compounds are transformed in four steps into the corresponding N-protected β,γ-methano-GABA derivatives, which are obtained for the first time in enantiomerically pure form. The corresponding transformations

  不饱和格氏试剂与手性酰胺之间的Kulinkovich-de Meijere反应具有很高的反式立体选择性，可方便地获得非外消旋的反式环丙胺。这些化合物经四个步骤转化为相应的N-保护的β，γ-甲基-GABA衍生物，它们首次以对映体纯形式获得。还描述了顺式环丙胺加合物的相应转化。