trans-2-(4'-Nitro-phenyl)-cyclopropan-carbonsaeure-ethylester | 406459-08-3

• 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: trans-2-(4'-Nitro-phenyl)-cyclopropan-carbonsaeure-ethylester
• 英文别名: Ethyl (1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylate
• CAS: 406459-08-3
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: MZTNKLFZFLDHMS-WDEREUQCSA-N

物化性质

• 沸点：
  349.6±35.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  重氮乙酸乙酯 、 4-硝基苯乙烯 在 (CuOTf)*toluene 、 (S,S)-(-)-2,2'-异亚丙基双(4-叔丁基-2-恶唑啉) 作用下， 以 氯仿 为溶剂， 生成 环丙羧酸,2-(4-硝基苯基)-,乙基酯,(1R,2R)-rel- 、 trans-2-(4'-Nitro-phenyl)-cyclopropan-carbonsaeure-ethylester
  参考文献：
  名称：

  Synthesis and activity of small molecule GPR40 agonists

  摘要：

  The first report on the identification and structure-activity relationships of a novel series of GPR40 agonists based on a 3(4-{[N-alkyl]amino phenyl)propanoic acid template is described. Structural modifications to the original screening hit yielded compounds with a 100-fold increase in potency at the human GPR40 receptor and pEC(50)s in the low nanomolar range. The carboxylic acid moiety is not critical for activity but typically elicits an agonistic response higher than those observed with carboxamide replacements. These compounds may prove useful in unraveling the therapeutic potential of this receptor for the treatment of Type 2 diabetes. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.007

文献信息

• Chiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed cyclopropanation
  作者：Anthony Labelle、Bruce A. Arndtsen

  DOI：10.1039/d2cc05924j

  日期：——

  Studies on a new type of chiral BINOL-based boron counterion highlights its ability to rearrange under the reaction conditions to create a ligand that can be used in the copper-catalyzed cyclopropanation of alkenes.

  对一种新型手性BINOL基硼对离子的研究表明，它能够在反应条件下重排，生成可用于铜催化的烯烃环丙基化反应的配体。
• Synthesis and activity of small molecule GPR40 agonists
  作者：Dulce M. Garrido、David F. Corbett、Kate A. Dwornik、Aaron S. Goetz、Thomas R. Littleton、Steve C. McKeown、Wendy Y. Mills、Terrence L. Smalley、Celia P. Briscoe、Andrew J. Peat

  DOI：10.1016/j.bmcl.2006.01.007

  日期：2006.4

  The first report on the identification and structure-activity relationships of a novel series of GPR40 agonists based on a 3(4-[N-alkyl]amino phenyl)propanoic acid template is described. Structural modifications to the original screening hit yielded compounds with a 100-fold increase in potency at the human GPR40 receptor and pEC(50)s in the low nanomolar range. The carboxylic acid moiety is not critical for activity but typically elicits an agonistic response higher than those observed with carboxamide replacements. These compounds may prove useful in unraveling the therapeutic potential of this receptor for the treatment of Type 2 diabetes. (C) 2006 Elsevier Ltd. All rights reserved.