(1S,2R)-2-(2-Methoxyphenyl)cyclopropane-1-carboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,2R)-2-(2-Methoxyphenyl)cyclopropane-1-carboxylic acid
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: QWTOSVJYKMLFEP-IUCAKERBSA-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：

  (1S,2R)-2-(2-Methoxyphenyl)cyclopropane-1-carboxylic acid 在 盐酸 、 二苯基膦叠氮化物 、 三乙胺 作用下， 反应 32.0h， 生成 (1S,2R)-2-(2-Methoxy-phenyl)-cyclopropylamine
  参考文献：
  名称：

  N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine-receptor agonists

  摘要：

  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.

  DOI：

  10.1021/jm00396a014
• 作为产物：
  描述：

  2-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 甲苯 为溶剂， 生成 (1S,2R)-2-(2-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

• Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide
  作者：Ruben Martin、Toni Moragas

  DOI：10.1055/s-0035-1560439

  日期：——

  Abstract A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components

  摘要 已经开发了镍催化的还原羧化技术来合成环丙烷羧酸。这种对用户友好且温和的转化过程在二氧化碳的大气压下进行，并利用有机卤化物或烯烃前体，因此代表了缺少相邻π组分的次要对位物的催化还原羧化反应的第一个实例。 已经开发了镍催化的还原羧化技术来合成环丙烷羧酸。这种对用户友好且温和的转化过程在二氧化碳的大气压下进行，并利用有机卤化物或烯烃前体，因此代表了缺少相邻π组分的次要对位物的催化还原羧化反应的第一个实例。
• 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.
• Derivatives of 2-arylcyclopropylamine: Synthesis and interactions with 5-HT1A receptors.
  作者：Ulf Appelberg、Nina Mohell、Uli Hacksell

  DOI：10.1016/0960-894x(96)00045-5

  日期：1996.2

  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.