α-Carbomethoxy-α-brom-β-phenyl-γ-nitro-buttersaeuremethylester | 4674-93-5

• 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: α-Carbomethoxy-α-brom-β-phenyl-γ-nitro-buttersaeuremethylester
• 英文别名: bromo-(2-nitro-1-phenyl-ethyl)-malonic acid dimethyl ester；Brom-(2-nitro-1-phenyl-aethyl)-malonsaeure-dimethylester；α-Brom-γ-nitro-β-phenyl-propan-α.α-dicarbonsaeure-dimethylester；Propanedioic acid, 2-bromo-2-(2-nitro-1-phenylethyl)-, dimethyl ester；dimethyl 2-bromo-2-(2-nitro-1-phenylethyl)propanedioate
• CAS: 4674-93-5
• 化学式: C₁₃H₁₄BrNO₆
• 分子量: 360.161
• InChiKey: JCIAXZIDRYKZPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-Carbomethoxy-α-brom-β-phenyl-γ-nitro-buttersaeuremethylester 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 trans-2-phenyl-3-nitrocyclopropane-1,1-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of functionalised cyclopropanes from nitroalkenes via an organocatalysed Michael-initiated ring-closure approach

  摘要：

  Synthetically useful nitrocyclopropanes are easily obtained via Michael addition of dimethyl bromomalonate to nitrostyrenes promoted by commercially available (S)-alpha,alpha-di-beta-naphthlyl-2-pyrrolidinemethanol as the catalyst, followed by DABCO-mediated intramolecular nucleophilic substitution. The functionalised nitrocyclopropanes are obtained in good yield, excellent diastereoselectivity and up to 49% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.005
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯仿 、 溴 作用下， 生成 α-Carbomethoxy-α-brom-β-phenyl-γ-nitro-buttersaeuremethylester
  参考文献：
  名称：

  STUDIES IN THE CYCLOPROPANE SERIES. XII. NITROCYCLOPROPANES

  摘要：

  DOI：

  10.1021/ja01364a066

文献信息

• Sopova,A.S. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 844 - 849
  作者：Sopova,A.S. et al.

  DOI：——

  日期：——
• Kohler, Engelbrecht, Journal of the American Chemical Society, 1919, vol. 41, p. 766
  作者：Kohler, Engelbrecht

  DOI：——

  日期：——
• STUDIES IN THE CYCLOPROPANE SERIES. XII. NITROCYCLOPROPANES
  作者：E. P. Kohler、S. F. Darling

  DOI：10.1021/ja01364a066

  日期：1930.1
• Stereoselective synthesis of functionalised cyclopropanes from nitroalkenes via an organocatalysed Michael-initiated ring-closure approach
  作者：Alessio Russo、Alessandra Lattanzi

  DOI：10.1016/j.tetasy.2010.04.005

  日期：2010.5

  Synthetically useful nitrocyclopropanes are easily obtained via Michael addition of dimethyl bromomalonate to nitrostyrenes promoted by commercially available (S)-alpha,alpha-di-beta-naphthlyl-2-pyrrolidinemethanol as the catalyst, followed by DABCO-mediated intramolecular nucleophilic substitution. The functionalised nitrocyclopropanes are obtained in good yield, excellent diastereoselectivity and up to 49% ee. (C) 2010 Elsevier Ltd. All rights reserved.