N-(1-diethoxyphosphoryl-2-ethenylcyclopropyl)-1-phenylmethanimine | 1217000-14-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: N-(1-diethoxyphosphoryl-2-ethenylcyclopropyl)-1-phenylmethanimine
• CAS: 1217000-14-0
• 化学式: C₁₆H₂₂NO₃P
• 分子量: 307.329
• InChiKey: SMSZZSCGROBRGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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， 生成 vinyl cyclopropylamino diethylphosphonate
  参考文献：
  名称：

  [EN] ANTIVIRAL PHOSPHINATE COMPOUNDS
  [FR] COMPOSÉS ANTIVIRAUX DE PHOSPHINATE

  摘要：

  公开号：

  WO2008005565A9
• 作为产物：
  描述：

  1,4-二溴-2-丁烯 、 [(亚苄基胺)甲基]磷酸二乙酯 在 caesium hydroxide monohydrate 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-(1-diethoxyphosphoryl-2-ethenylcyclopropyl)-1-phenylmethanimine
  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

• [EN] ANTIVIRAL PHOSPHINATE COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX DE PHOSPHINATE
  申请人：GILEAD SCIENCES INC

  公开号：WO2008005565A9

  公开（公告）日：2009-01-29
• Discovery of novel phosphonate derivatives as hepatitis C virus NS3 protease inhibitors
  作者：X. Christopher Sheng、Hyung-Jung Pyun、Kleem Chaudhary、Jianying Wang、Edward Doerffler、Melissa Fleury、Darren McMurtrie、Xiaowu Chen、William E. Delaney、Choung U. Kim

  DOI：10.1016/j.bmcl.2009.05.023

  日期：2009.7

  A novel class of phosphonate derivatives was designed to mimic the interaction of product-like carboxylate based inhibitors of HCV NS3 protease. A phosphonic acid (compound 2) was demonstrated to be a potent HCV NS3 protease inhibitor, and a potential candidate for treating HCV infection. The syntheses and preliminary biological evaluation of this phosphonate class of inhibitor are described. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.