7-[diethoxy(oxido)phosphaniumyl]-2-phenyl-2,3-dihydro-1H-azepine | 1173279-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 7-[diethoxy(oxido)phosphaniumyl]-2-phenyl-2,3-dihydro-1H-azepine
• CAS: 1173279-68-9
• 化学式: C₁₆H₂₂NO₃P
• 分子量: 307.329
• InChiKey: XTQQOXQUBJJVKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(1-diethoxyphosphoryl-2-ethenylcyclopropyl)-1-phenylmethanimine 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以12 g的产率得到1-amino-2-vinyl-cyclopropane-1-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and resolution of diethyl (1S,2S)-1-amino-2-vinylcyclopropane-1-phosphonate for HCV NS3 protease inhibitors

  摘要：

  We herein describe an efficient synthesis of optically active diethyl 1-amino-2-vinylcyclopropane-1-phosphonate (analogous to 1-amino-2-vinylcyclopropane-1-carboxylate). The racemic phosphonate diethyl ester was obtained from an imine derived from aminomethylphosphonate diester and trans-1,4-dibromo-2-butene. Crystallizations of the dibenzoyl-L-tartaric acid salt allowed for separation of enantiomers. The enantiomerically pure material was used to synthesize an extremely potent tripeptide phosphonate inhibitor of HCV NS3 protease. X-ray crystal structure of the inhibitor bound to the HCV NS3 protease confirmed the absolute stereochemistry of the title compound. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.044

文献信息

• Synthesis and resolution of diethyl (1S,2S)-1-amino-2-vinylcyclopropane-1-phosphonate for HCV NS3 protease inhibitors
  作者：Hyung-Jung Pyun、Kleem Chaudhary、John R. Somoza、X. Christopher Sheng、Choung U. Kim

  DOI：10.1016/j.tetlet.2009.04.044

  日期：2009.7

  We herein describe an efficient synthesis of optically active diethyl 1-amino-2-vinylcyclopropane-1-phosphonate (analogous to 1-amino-2-vinylcyclopropane-1-carboxylate). The racemic phosphonate diethyl ester was obtained from an imine derived from aminomethylphosphonate diester and trans-1,4-dibromo-2-butene. Crystallizations of the dibenzoyl-L-tartaric acid salt allowed for separation of enantiomers. The enantiomerically pure material was used to synthesize an extremely potent tripeptide phosphonate inhibitor of HCV NS3 protease. X-ray crystal structure of the inhibitor bound to the HCV NS3 protease confirmed the absolute stereochemistry of the title compound. (c) 2009 Elsevier Ltd. All rights reserved.