(cis)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (cis)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate
• 英文别名: (cis)-Ethyl-2-(4-aminophenyl)cyclopropanecarboxylate；ethyl (1R,2S)-2-(4-aminophenyl)cyclopropane-1-carboxylate
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: PRQHGNILEBKMGD-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (cis)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate 在 叠氮磷酸二苯酯 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 异丙醇 、 苯 为溶剂， 反应 17.0h， 生成 tert-butyl (1R,2R)-2-(3-benzamidophenyl)cyclopropylcarbamate
  参考文献：
  名称：

  Pure enantiomers of benzoylamino-tranylcypromine: LSD1 inhibition, gene modulation in human leukemia cells and effects on clonogenic potential of murine promyelocytic blasts

  摘要：

  The pure enantiomers of the N-(2-, 3-, and 4-(2-aminocyclopropyl)phenyl)benzamides hydrochlorides 11a-j were prepared and tested against LSD1 and MAO enzymes. The evaluation of the regioisomers 11a-j highlighted a net increase of the anti-LSD1 potency by shifting the benzamide moiety from ortho to meta and mainly to para position of tranylcypromine phenyl ring, independently from their trans or cis stereochemistry. In particular, the para-substituted 11a,b (trans) and 11g,h (cis) compounds displayed LSD1 and MAO-A inhibition at low nanomolar levels, while were less potent against MAO-B. The meta analogs 11c,d (trans) and 11i,j (cis) were in general less potent, but more efficient against MAO-A than against LSD1. In cellular assays, all the para and meta enantiomers were able to inhibit LSD1 by inducing Gfi-1b and ITGAM gene expression, with 11b,c and 11g-i giving the highest effects. Moreover, 11b and 11g,h strongly inhibited the clonogenic potential of murine promyelocytic blasts. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.060
• 作为产物：
  描述：

  4-硝基苯乙烯 在 palladium diacetate sodium sulfide 、 sulfur 作用下， 以 乙醇 为溶剂， 生成 (cis)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Substituent effects on the13C NMR spectra of ethylcis- andtrans-2-(p-substituted-phenyl)-1-cyclopanecarboxylates

  摘要：

  对一系列的乙基顺式和反式-2-（对取代苯基）-1-环丙烷羧酸酯进行了13C NMR谱测定。讨论了苯环对位取代基和几何构型对化学位移的影响。

  DOI：

  10.1002/mrc.1260300415

文献信息

• Substituent effects on the13C NMR spectra of ethylcis- andtrans-2-(p-substituted-phenyl)-1-cyclopanecarboxylates
  作者：Yoshiaki Kusuyama、Kenjiro Tokami

  DOI：10.1002/mrc.1260300415

  日期：1992.4

  13C NMR spectra were measured for a series of ethyl cis- and trans-2-(p-substituted - phenyl) - 1 - cyclopropanecarboxylates. The effects of the para substituents and the geometry on the chemical shifts are discussed.

  对一系列的乙基顺式和反式-2-（对取代苯基）-1-环丙烷羧酸酯进行了13C NMR谱测定。讨论了苯环对位取代基和几何构型对化学位移的影响。
• AMINOPHENYLCYCLOPROPYL CARBOXYLIC ACIDS AND DERIVATIVES AS AGONISTS TO GPR40
  申请人：Corbett David Francis

  公开号：US20090105257A1

  公开（公告）日：2009-04-23

  The present invention relates generally to novel therapeutic compounds and more particularly to novel compounds, their use as GPR40 agonists, processes for their manufacture, and intermediates useful in their preparation.

  本发明通常涉及新型治疗化合物，更特别地涉及新型化合物，其用作GPR40激动剂，其制造过程以及其制备中有用的中间体。
• Aminophenylcyclopropyl carboxylic acids and derivatives as agonists to GPR40
  申请人：GlaxoSmithKline LLC

  公开号：US07834013B2

  公开（公告）日：2010-11-16

  The present invention relates generally to novel therapeutic compounds and more particularly to novel compounds, their use as GPR40 agonists, processes for their manufacture, and intermediates useful in their preparation.

  本发明一般涉及新型治疗化合物，更具体地涉及新型化合物，其作为GPR40激动剂的用途，其制造过程以及在其制备中有用的中间体。
• Stereo-controlled cyclopropanation catalysis within the confined pores of porphyrin MOFs
  作者：Karina Hemmer、Raphael Bühler、Martin Elsner、Mirza Cokoja、Roland A. Fischer

  DOI：10.1039/d2cy02144g

  日期：——

  Three Rh-porphyrin MOF catalysts show a MOF topology independent stereoselectivity enhancement for styrene derivatives with coordinating functionalities. Upon donor molecule addition, the activity is increased facilitating Rh-carbene formation.

  三种 Rh-卟啉 MOF 催化剂显示出 MOF 拓扑与配位官能团无关，可提高苯乙烯衍生物的立体选择性。添加供体分子后，活性会提高，从而促进 Rh-羰基的形成。
• Pure enantiomers of benzoylamino-tranylcypromine: LSD1 inhibition, gene modulation in human leukemia cells and effects on clonogenic potential of murine promyelocytic blasts
  作者：Sergio Valente、Veronica Rodriguez、Ciro Mercurio、Paola Vianello、Bruna Saponara、Roberto Cirilli、Giuseppe Ciossani、Donatella Labella、Biagina Marrocco、Daria Monaldi、Giovanni Ruoppolo、Mats Tilset、Oronza A. Botrugno、Paola Dessanti、Saverio Minucci、Andrea Mattevi、Mario Varasi、Antonello Mai

  DOI：10.1016/j.ejmech.2015.02.060

  日期：2015.4

  The pure enantiomers of the N-(2-, 3-, and 4-(2-aminocyclopropyl)phenyl)benzamides hydrochlorides 11a-j were prepared and tested against LSD1 and MAO enzymes. The evaluation of the regioisomers 11a-j highlighted a net increase of the anti-LSD1 potency by shifting the benzamide moiety from ortho to meta and mainly to para position of tranylcypromine phenyl ring, independently from their trans or cis stereochemistry. In particular, the para-substituted 11a,b (trans) and 11g,h (cis) compounds displayed LSD1 and MAO-A inhibition at low nanomolar levels, while were less potent against MAO-B. The meta analogs 11c,d (trans) and 11i,j (cis) were in general less potent, but more efficient against MAO-A than against LSD1. In cellular assays, all the para and meta enantiomers were able to inhibit LSD1 by inducing Gfi-1b and ITGAM gene expression, with 11b,c and 11g-i giving the highest effects. Moreover, 11b and 11g,h strongly inhibited the clonogenic potential of murine promyelocytic blasts. (C) 2015 Elsevier Masson SAS. All rights reserved.