(+/-)-(1R,2S)-2-(1-methylethoxycarbonyl)-1-cyclopropanecarboxylic acid

• 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: (+/-)-(1R,2S)-2-(1-methylethoxycarbonyl)-1-cyclopropanecarboxylic acid
• 英文别名: (1R,2S)-2-propan-2-yloxycarbonylcyclopropane-1-carboxylic acid
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: DWWOWEVEYNNOIT-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (+/-)-(1R,2S)-2-(1-methylethoxycarbonyl)-1-cyclopropanecarboxylic acid 在 sodium tetrahydroborate 、 草酰氯 、 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 13.5h， 生成 (1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Synthesis, stereochemistry, and chiroptical spectra of cyclopropyl lactones and thionolactones

  摘要：

  Several optically active substituted 3-oxabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues were synthesized, and their circular dichroism spectra are reported. It was found that the n-pi* Cotton effect sign is determined by the helicity of an inherently chiral chromophore formed by the lactone or thiolactone group and the cyclopropyl moiety. The pi-pi* Cotton effect of thiocarbonyl compounds shows opposite sign to that observed for the lowest energy transition. The crystal structures of two compounds were solved to establish their molecular geometries. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00419-3
• 作为产物：
  描述：

  1,2-环丙烷二羧酸 在 吡啶 、 乙酸酐 作用下， 反应 1.5h， 生成 (+/-)-(1R,2S)-2-(1-methylethoxycarbonyl)-1-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis, stereochemistry, and chiroptical spectra of cyclopropyl lactones and thionolactones

  摘要：

  Several optically active substituted 3-oxabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues were synthesized, and their circular dichroism spectra are reported. It was found that the n-pi* Cotton effect sign is determined by the helicity of an inherently chiral chromophore formed by the lactone or thiolactone group and the cyclopropyl moiety. The pi-pi* Cotton effect of thiocarbonyl compounds shows opposite sign to that observed for the lowest energy transition. The crystal structures of two compounds were solved to establish their molecular geometries. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00419-3

文献信息

• Fluoroalkyl-Substituted Cyclopropane Derivatives: Synthesis and Physicochemical Properties
  作者：Anton V. Chernykh、Oleksandr S. Olifir、Yuliya O. Kuchkovska、Dmitriy M. Volochnyuk、Vladimir S. Yarmolchuk、Oleksandr O. Grygorenko

  DOI：10.1021/acs.joc.0c01848

  日期：2020.10.2

  for the obtained compounds or their derivatives to evaluate the influence of the type and relative position of fluoroalkyl substituents on the acidity and lipophilicity of monofunctionalized cyclopropanes. An analysis of the selected products by X-ray crystallography was carried out to obtain a better insight into the observed differences in physicochemical properties.

  用不同的方法以克数级合成了一系列带有CH 2 F，CHF 2和CF 3取代基的全部12种顺式和反式环丙烷羧酸和环丙胺。测量获得的化合物或其衍生物的解离常数（p K a）和log  P值，以评估氟代烷基取代基的类型和相对位置对单官能化环丙烷的酸度和亲脂性的影响。通过X射线晶体学对所选产品进行了分析，以更好地了解所观察到的理化性质差异。
• Cyclopropane derivatives as potential human serine racemase inhibitors: unveiling novel insights into a difficult target
  作者：Claudia Beato、Chiara Pecchini、Chiara Cocconcelli、Barbara Campanini、Marialaura Marchetti、Marco Pieroni、Andrea Mozzarelli、Gabriele Costantino

  DOI：10.3109/14756366.2015.1057720

  日期：2016.7.3

  D-Serine is the co-agonist of NMDA receptors and binds to the so-called glycine site. D-Serine is synthesized by human serine racemase (SR). Over activation of NMDA receptors is involved in many neurodegenerative diseases and, therefore, the inhibition of SR might represent a novel strategy for the treatment of these pathologies. SR is a very difficult target, with only few compounds so far identified exhibiting weak inhibitory activity. This study was aimed at the identification of novel SR inhibitor by mimicking malonic acid, the best-known SR inhibitor, with a cyclopropane scaffold. We developed, synthesized, and tested a series of cyclopropane dicarboxylic acid derivatives, complementing the synthetic effort with molecular docking. We identified few compounds that bind SR in high micromolar range with a lack of significant correlation between experimental and predicted binding affinities. The thorough analysis of the results can be exploited for the development of more potent SR inhibitors.
• Stereochemistry and chiroptical spectra of 3-azabicyclo[3.1.0]hexan-2-ones and thiones
  作者：Maria J. Milewska、Maria Gdaniec、Tadeusz Poloński

  DOI：10.1016/s0957-4166(97)00111-0

  日期：1997.4

  Several optically active substituted 3-azabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues have been synthesized, and their circular dichroism spectra studied. The crystal structure of thiolactam 1a showed that the bicyclic skeleton of the title compounds assumes a sofa-like geometry. It is postulated that the cyclopropyl moiety and amide or thioamide group constitute an inherently chiral chromophore, helicity of which determines the Cotton effect sign corresponding to the n-pi* electronic transition. The weak pi-pi* Cotton effect of thiolactams shows opposite sign to that observed for the lowest energy excitation. (C) 1997 Elsevier Science Ltd.
• Synthesis of optically active monothioimides with chirality due to sulphur substitution
  作者：Maria J. Milewska、Tadeusz Połoński

  DOI：10.1016/s0957-4166(00)86206-0

  日期：1994.3

  Two optically active bicyclic monothioimides were prepared via chiral derivatives of cis-1,2-cyclopropanedicarboxylic and cis-1,3-cyclopentanedicarboxylic acids and their absolute configurations were assigned.