diethyl 2-(3-bromo-3-phenylpropyl)malonate | 94163-58-3

• 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: diethyl 2-(3-bromo-3-phenylpropyl)malonate
• 英文别名: diethyl α-(3-bromopropyl-3-phenyl) malonate；<3-Brom-3-phenyl-propyl>-malonsaeure-diaethylester；Diethyl 2-(3-bromo-3-phenylpropyl)propanedioate
• CAS: 94163-58-3
• 化学式: C₁₆H₂₁BrO₄
• 分子量: 357.244
• InChiKey: PELLXVROELGBIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(3-bromo-3-phenylpropyl)malonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到diethyl 2-phenylcyclobutane-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

  摘要：

  All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.015
• 作为产物：
  描述：

  (1,3-二溴丙基)苯 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 diethyl 2-(3-bromo-3-phenylpropyl)malonate
  参考文献：
  名称：

  Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

  摘要：

  All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.015

文献信息

• Zur Kenntnis cyclischer Acylale, 9. Mitt.: Die Einwirkung von Diazomethan auf Isopropyliden-benzylidenmalonat
  作者：Gertrude Swoboda、A. Eitel、J. Swoboda、F. Wessely

  DOI：10.1007/bf00904733

  日期：——