(1S,2R)-1-phenyl-1,2-cyclopropanedicarboxylic acid | 55221-23-3

• 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: (1S,2R)-1-phenyl-1,2-cyclopropanedicarboxylic acid
• 英文别名: (1S,2R)-1-phenylcyclopropane-1,2-dicarboxylic acid
• CAS: 55221-23-3
• 化学式: C₁₁H₁₀O₄
• mdl: MFCD17167240
• 分子量: 206.198
• InChiKey: CPBWKVACBJABJR-GZMMTYOYSA-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-phenyl-1,2-cyclopropanedicarboxylic acid 在 乙酰氯 作用下， 生成 (1S,2R)-N-methyl-1-phenyl-1,2-cyclopropanedicarboximide
  参考文献：
  名称：

  Chiroptical properties of 1,2-cyclopropanedicarboxylic anhydrides and imides. The cyclopropane ring contribution to the Cotton effect

  摘要：

  Several optically active 1,2-cyclopropanedicarboxylic anhydrides and imides were prepared and their chiroptical spectra studied. Despite the strained bicyclic skeleton of these compounds, their CD spectra show an unusual solvent dependence. This phenomenon can be explained in terms of the cyclopropane ring contribution to the Cotton effect. A deviation of the skeleton and the anhydride or imide group from the local C(s) symmetry, shown by MNDO calculations, causes formation of an inherently chiral chromophore constituted by the three-membered ring and neighboring carbonyls. This kind of chromophore is responsible for the observed strong Cotton effects.

  DOI：

  10.1021/jo00064a034
• 作为产物：
  描述：

  1-phenylcyclopropanedicarboxylic acid 以67%的产率得到
  参考文献：
  名称：

  STANEK, JAROSLAV;ALDER, ALEX;BELLUS, DANIEL;BHATNAGAR, AJAY S.;HAUSLER, A+, J. MED. CHEM., 34,(1991) N, C. 1329-1334

  摘要：

  DOI：

文献信息

• Synthesis and aromatase inhibitory activity of novel 1-(4-aminophenyl)-3-azabicyclo[3.1.0]hexane- and -[3.1.1]heptane-2,4-diones
  作者：Jaroslav Stanek、Alex Alder、Daniel Bellus、Ajay S. Bhatnagar、Albert Haeusler、Klaus Schieweck

  DOI：10.1021/jm00108a013

  日期：1991.4

  to estrogens. All of them displayed enzyme-inhibiting activity, and 3-cyclohexyl derivative 2g and 3-cyclohexylmethyl derivative 1h both proved more potent (greater than 140-fold) than the clinically effective agent aminoglutethimide [3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione, AG]. As with AG and its derivatives, the 1R-(+)-enantiomer of 1h was responsible for the enzyme inhibitory activity. These

  3-（环己甲基）-1-（4-氨基苯基）-3-氮杂双环[3.1.0]己烷-2、4-二酮（1h）及其旋光对映体和一系列新的非手性1-（-描述了4-氨基苯基）-3-氮杂双环[3.1.1]庚烷-2,4-二酮（2a-i，k）。在体外测试了这些化合物对人胎盘芳香酶的抑制作用，后者是一种细胞色素P450依赖性酶，负责将雄激素转化为雌激素。它们均显示出酶抑制活性，并且3-环己基衍生物2g和3-环己基甲基衍生物1h均被证明比临床上有效的药物氨基戊二酰亚胺[3-（4-氨基苯基）-3-乙基哌啶]更有效（大于140倍）。 -2,6-dione，AG]。与AG及其衍生物一样，1h的1R-（+）-对映异构体负责酶的抑制活性。
• Absolute Configuration of Some Chiral Cyclopropanes
  作者：Kazuyoshi Nishiyama、Jun’ichi Oda、Yuzo Inouye

  DOI：10.1246/bcsj.47.3175

  日期：1974.12

  The absolute configurations of (1S : 2R)-(−)-cis-, and (1S : 2S)-(+)-trans-1-phenylcyclopropane-1,2-dicarboxylic acids, and (1S : 2R)-(−)-cis-, and (1S : 2S)-(+)-trans-1-phenyl-1,2-bis(acetoxymethyl)cyclopropanes were established by correlation to (R)-(−)-2,2-diphenylcyclopropane-1-carboxylic acid.

  (1S : 2R)-(-)-cis- 和 (1S : 2S)-(+)-trans-1-phenylcyclopropane-1,2-二羧酸和 (1S : 2R)-(- )-顺-和 (1S: 2S)-(+)-反-1-苯基-1,2-双(乙酰氧基甲基)环丙烷通过与 (R)-(-)-2,2-二苯基环丙烷的相关性建立- 1-羧酸。
• Nickel‐Catalyzed Asymmetric Hydroaryloxy‐ and Hydroalkoxycarbonylation of Cyclopropenes
  作者：Rongrong Yu、Song‐Zhou Cai、Can Li、Xianjie Fang

  DOI：10.1002/anie.202200733

  日期：2022.9.5

  Highly enantioselective inter- and intramolecular Ni-catalyzed hydroalkoxycarbonylation yields various enantioenriched polysubstituted cyclopropanecarboxylic derivatives with quaternary carbon stereocenters.

  高度对映选择性的分子间和分子内 Ni 催化的氢化烷氧基羰基化产生各种具有季碳立体中心的对映富集的多取代环丙烷羧酸衍生物。
• STANEK, JAROSLAV;ALDER, ALEX;BELLUS, DANIEL;BHATNAGAR, AJAY S.;HAUSLER, A+, J. MED. CHEM., 34,(1991) N, C. 1329-1334
  作者：STANEK, JAROSLAV、ALDER, ALEX、BELLUS, DANIEL、BHATNAGAR, AJAY S.、HAUSLER, A+

  DOI：——

  日期：——
• Substituierte Azabicycloalkane, ihre Verwendung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verfahren zur Herstellung dieser Verbindungen
  申请人：CIBA-GEIGY AG

  公开号：EP0114033B1

  公开（公告）日：1988-10-12