methyl trans-2-(p-methoxyphenyl)cyclopropanecarboxylate | 72228-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl trans-2-(p-methoxyphenyl)cyclopropanecarboxylate
• 英文别名: methyl 2-(4-methoxyphenyl)cyclopropanecarboxylate；trans-2-(4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester；Methyl (1S,2S)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate
• CAS: 72228-95-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: XMGQSHLGMZJUJV-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl trans-2-(p-methoxyphenyl)cyclopropanecarboxylate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 trans-2-(4-methoxyphenyl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  [EN] PHENYLALANINE DERIVATIVES AND THEIR USE AS NON-PEPTIDE GLP-1 RECEPTOR MODULATORS
  [FR] DÉRIVÉS PHÉNYLALANINES ET LEUR UTILISATION COMME MODULATEURS NON PEPTIDIQUES DU RÉCEPTEUR DE GLP-1

  摘要：

  本文提供了非肽类GLP-1受体调节剂化合物，例如，Formula (I)的化合物，包括这些化合物的药物组合物，以及其制备方法。还提供了这些化合物用于治疗代谢紊乱的方法。

  公开号：

  WO2011094890A1
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 palladium diacetate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl trans-2-(p-methoxyphenyl)cyclopropanecarboxylate
  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

文献信息

• Intermolecular Metal-Free Cyclopropanation of Alkenes Using Tosylhydrazones
  作者：José Barluenga、Noelia Quiñones、María Tomás-Gamasa、María-Paz Cabal

  DOI：10.1002/ejoc.201200149

  日期：2012.4

  We describe the first general method for the metal-free cyclopropanation of alkenes by using N-tosylhydrazones as an in situ source of diazo compounds. This new method works with a wide variety of alkenes (styrene derivatives, dienes, enynes, and electron-deficient alkenes) by using N-tosylhydrazones derived from various ketones or aldehydes (aromatic, aliphatic, enones). The reaction is performed

  我们描述了使用 N-甲苯磺酰腙作为重氮化合物的原位来源进行烯烃无金属环丙烷化的第一种通用方法。这种新方法使用衍生自各种酮或醛（芳香族、脂肪族、烯酮）的 N-甲苯磺酰腙，适用于各种烯烃（苯乙烯衍生物、二烯、烯炔和缺电子烯烃）。该反应是使用 K2CO3 作为碱进行的，以形成重氮物质，并与多种官能团相容。
• Transition-metal-catalyzed reactions of diazo compounds. 1. Cyclopropanation of double bonds
  作者：Andre J. Anciaux、Andre J. Hubert、Alfred F. Noels、N. Petiniot、Philippe Teyssie

  DOI：10.1021/jo01292a029

  日期：1980.2
• [EN] PHENYLALANINE DERIVATIVES AND THEIR USE AS NON-PEPTIDE GLP-1 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS PHÉNYLALANINES ET LEUR UTILISATION COMME MODULATEURS NON PEPTIDIQUES DU RÉCEPTEUR DE GLP-1
  申请人：ARGUSINA INC

  公开号：WO2011094890A1

  公开（公告）日：2011-08-11

  Provided herein are non-peptide GLP-1 receptor modulator compounds, for example, of Formula (I), pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of a metabolic disorder.

  本文提供了非肽类GLP-1受体调节剂化合物，例如，Formula (I)的化合物，包括这些化合物的药物组合物，以及其制备方法。还提供了这些化合物用于治疗代谢紊乱的方法。
• 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.