(1R,2S)-2-(3-methoxyphenyl)cyclopropane-1-carboxylic acid | 110901-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,2S)-2-(3-methoxyphenyl)cyclopropane-1-carboxylic acid
• CAS: 110901-90-1
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: SEQTZPLHSZFWIY-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(3-methoxyphenyl)cyclopropane-1-carboxylic acid 生成 (1S,2S)-2-(3-methoxyphenyl)cyclopropan-1-amine
  参考文献：
  名称：

  Derivatives of 2-arylcyclopropylamine: Synthesis and interactions with 5-HT1A receptors.

  摘要：

  A series of cis- and trans-derivatives of 2-aryl-N,N-dipropylcyclopropylamines and 1-(2-arylcyclopropyl)-N,N-dipropylmethylamines were synthesized and evaluated for affinity at the 5-HT1A receptor. The key step in the syntheses was a cyclopropanation of cis- and trans-3-arylpropenoic esters with diazomethane which proceeds with retention of the stereochemistry. cis-1-[2-(3-Methoxyphenyl)cyclopropyl]-N,N-dipropylmethylamine (32) had the highest 5-HT1A-receptor affinity (K-i = 58 nM) of the novel derivatives.

  DOI：

  10.1016/0960-894x(96)00045-5
• 作为产物：
  描述：

  3-乙炔基苯甲醚 在 Lindlar's catalyst 、 增效醚 喹啉 、 palladium diacetate 、 sodium hydroxide 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 (1R,2S)-2-(3-methoxyphenyl)cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Derivatives of 2-arylcyclopropylamine: Synthesis and interactions with 5-HT1A receptors.

  摘要：

  A series of cis- and trans-derivatives of 2-aryl-N,N-dipropylcyclopropylamines and 1-(2-arylcyclopropyl)-N,N-dipropylmethylamines were synthesized and evaluated for affinity at the 5-HT1A receptor. The key step in the syntheses was a cyclopropanation of cis- and trans-3-arylpropenoic esters with diazomethane which proceeds with retention of the stereochemistry. cis-1-[2-(3-Methoxyphenyl)cyclopropyl]-N,N-dipropylmethylamine (32) had the highest 5-HT1A-receptor affinity (K-i = 58 nM) of the novel derivatives.

  DOI：

  10.1016/0960-894x(96)00045-5

文献信息

• Pd(II)-Catalyzed Enantioselective C(sp³)–H Arylation of Free Carboxylic Acids
  作者：Peng-Xiang Shen、Liang Hu、Qian Shao、Kai Hong、Jin-Quan Yu

  DOI：10.1021/jacs.8b03509

  日期：2018.5.30

  chiral ligand based on an ethylenediamine backbone was developed to achieve Pd-catalyzed enantioselective C(sp3)-H arylation of cyclopropanecarboxylic and 2-aminoisobutyric acids without using exogenous directing groups. This new chiral catalyst affords new disconnection for preparing diverse chiral carboxylic acids from simple starting materials that are complementary to the various ring forming approaches

  开发了一种基于乙二胺骨架的单保护氨基乙胺手性配体，以实现 Pd 催化的环丙烷羧酸和 2-氨基异丁酸的对映选择性 C(sp3)-H 芳基化，而无需使用外源性导向基团。这种新的手性催化剂为从与各种成环方法互补的简单起始材料制备各种手性羧酸提供了新的断开连接。
• [EN] PD(II)-CATALYZED ENANTIOSELECTIVE C-H ARYLATION OF FREE CARBOXYLIC ACIDS<br/>[FR] ARYLATION C-H ÉNANTIOSÉLECTIVE CATALYSÉE PAR PD(II) D'ACIDES CARBOXYLIQUES LIBRES
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2019204477A1

  公开（公告）日：2019-10-24

  The invention includes procedures for stereoselective β-arylation of carboxylic acids having a β-carbon atom. For example, stereoselective arylation procedures include the following reactions: (I)

  这项发明涵盖了对具有β-碳原子的羧酸进行立体选择性β-芳基化的程序。例如，立体选择性芳基化程序包括以下反应：(I)
• Pd(II)-catalyzed enantioselective C—H arylation of free carboxylic acids
  申请人：The Scripps Research Institute

  公开号：US11021427B2

  公开（公告）日：2021-06-01

  The invention includes procedures for stereoselective β-acylation of carboxylic acids having a β-carbon atom. For example, stereoselective acylation procedures include the following reactions: (I)

  本发明包括对具有一个 β 碳原子的羧酸进行立体选择性 β-酰化的程序。例如，立体选择性酰化程序包括以下反应： (I)
• Total synthesis of aromatic steroids
  作者：Andrzej Robert Daniewski、Teresa Kowalczyk-Przewloka

  DOI：10.1021/jo00216a034

  日期：1985.8
• N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine-receptor agonists
  作者：Lars Erik Arvidsson、Anette M. Johansson、Uli Hacksell、J. Lars G. Nilsson、Kjell Svensson、Stephan Hjorth、Tor Magnusson、Arvid Carlsson、Per Lindberg

  DOI：10.1021/jm00396a014

  日期：1988.1

  N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.