rel-(1S,2R)-methyl 2-((E)-2-((tert-butoxycarbonyl)(phenyl)amino)vinyl)-1-phenylcyclopropanecarboxylate

• 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: rel-(1S,2R)-methyl 2-((E)-2-((tert-butoxycarbonyl)(phenyl)amino)vinyl)-1-phenylcyclopropanecarboxylate
• 英文别名: methyl (1S,2R)-2-[(E)-2-[N-[(2-methylpropan-2-yl)oxycarbonyl]anilino]ethenyl]-1-phenylcyclopropane-1-carboxylate
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: PNIUREGDRUSWQB-UKZVLQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rel-(1S,2R)-methyl 2-((E)-2-((tert-butoxycarbonyl)(phenyl)amino)vinyl)-1-phenylcyclopropanecarboxylate 在 盐酸 作用下， 以 氯仿 、 水 为溶剂， 反应 3.0h， 以90%的产率得到methyl 2-(2-oxoethyl)-1-phenylcyclopropanecarboxylate
  参考文献：
  名称：

  Copper(II)–acid catalyzed cyclopropanation of 1,3-dienamides by electrophilic activation of α-aryl diazoesters

  摘要：

  Copper(II)-acid catalyzed cyclopropanation of electron-rich alkenes, such as 1,3-dienamides, with cc-aryl diazoesters are described. The reaction could be performed without rare metal catalysts, excess substrate, or the need for the slow addition of the diazoesters. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.115
• 作为产物：
  描述：

  (Z)-tert-butyl (4-methoxybut-2-en-1-yl)(phenyl)carbamate 在 copper acetylacetonate 、 正丁基锂 、 三氟化硼乙醚 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 rel-(1S,2R)-methyl 2-((E)-2-((tert-butoxycarbonyl)(phenyl)amino)vinyl)-1-phenylcyclopropanecarboxylate
  参考文献：
  名称：

  Copper(II)–acid catalyzed cyclopropanation of 1,3-dienamides by electrophilic activation of α-aryl diazoesters

  摘要：

  Copper(II)-acid catalyzed cyclopropanation of electron-rich alkenes, such as 1,3-dienamides, with cc-aryl diazoesters are described. The reaction could be performed without rare metal catalysts, excess substrate, or the need for the slow addition of the diazoesters. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.115

文献信息

• Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1Z)-1-Amino- and (1Z)-1-Oxy-1,3-butadienyl Derivatives
  作者：Eiji Tayama、Shun Saito

  DOI：10.1055/s-0034-1380426

  日期：——

  The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with a-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.