ethyl (1R,2S)-2-phenyl-1-propylcyclopropanecarboxylate | 1241048-42-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (1R,2S)-2-phenyl-1-propylcyclopropanecarboxylate
• CAS: 1241048-42-9
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: CSRMEQHLVRPMRH-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl (1R,2S)-2-phenyl-1-propylcyclopropanecarboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 以57%的产率得到trans-2-phenyl-1-propylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis, biological activity and mechanistic insights of 1-substituted cyclopropylamine derivatives: A novel class of irreversible inhibitors of histone demethylase KDM1A

  摘要：

  Histone demethylase KDM1A (also known as LSD1) has become an attractive therapeutic target for the treatment of cancer as well as other disorders such as viral infections. We report on the synthesis of compounds derived from the expansion of tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. These compounds, which are substituted on the cyclopropyl core moiety, were evaluated for their ability to inhibit KDM1A in vitro as well as to function in cells by modulating the expression of Gfi-1b, a well recognized KDM1A target gene. The molecules were all found to covalently inhibit KDM1A and to become increasingly selective against human monoamine oxidases MAO A and MAO B through the introduction of bulkier substituents on the cyclopropylamine ring. Structural and biochemical analysis of selected trans isomers showed that the two stereoisomers are endowed with similar inhibitory activities against KDM1A, but form different covalent adducts with the FAD co-enzyme. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.068
• 作为产物：
  描述：

  氧化苯乙烯 、 2-膦酰戊酸三乙脂 在 正丁基锂 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.91h， 以89%的产率得到ethyl (1R,2S)-2-phenyl-1-propylcyclopropanecarboxylate
  参考文献：
  名称：

  Synthesis, biological activity and mechanistic insights of 1-substituted cyclopropylamine derivatives: A novel class of irreversible inhibitors of histone demethylase KDM1A

  摘要：

  Histone demethylase KDM1A (also known as LSD1) has become an attractive therapeutic target for the treatment of cancer as well as other disorders such as viral infections. We report on the synthesis of compounds derived from the expansion of tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. These compounds, which are substituted on the cyclopropyl core moiety, were evaluated for their ability to inhibit KDM1A in vitro as well as to function in cells by modulating the expression of Gfi-1b, a well recognized KDM1A target gene. The molecules were all found to covalently inhibit KDM1A and to become increasingly selective against human monoamine oxidases MAO A and MAO B through the introduction of bulkier substituents on the cyclopropylamine ring. Structural and biochemical analysis of selected trans isomers showed that the two stereoisomers are endowed with similar inhibitory activities against KDM1A, but form different covalent adducts with the FAD co-enzyme. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.068

文献信息

• Stereocontrolled synthesis of quaternary cyclopropyl esters
  作者：Christopher D. Bray、Fabrizio Minicone

  DOI：10.1039/c0cc01333a

  日期：——

  Treatment of a variety of enantiopure terminal epoxides with the anion of a range of 2-substituted triethylphosphonoacetates leads to an array of quaternary cyclopropyl esters with high yield and diastereocontrol.

  用一系列 2-取代的三乙基膦酰基乙酸阴离子处理各种对映体纯末端环氧化物，可得到一系列高产率和非对映控制的季环丙基酯。
• DeAngelis, Andrew; Dmitrenko, Olga; Yap, Glenn P. A., Journal of the American Chemical Society, 2009, vol. 131, p. 7230 - 7231
  作者：DeAngelis, Andrew、Dmitrenko, Olga、Yap, Glenn P. A.、Fox, Joseph M.

  DOI：——

  日期：——