(R)-ethyl 2-(3,4-dichlorophenyl)-2-hydroxy-3-nitropropanoate | 1239279-18-5

• 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: (R)-ethyl 2-(3,4-dichlorophenyl)-2-hydroxy-3-nitropropanoate
• 英文别名: ethyl (2R)-2-(3,4-dichlorophenyl)-2-hydroxy-3-nitropropanoate
• CAS: 1239279-18-5
• 化学式: C₁₁H₁₁Cl₂NO₅
• 分子量: 308.118
• InChiKey: HAZUPZNLYBOGCB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 2-(3,4-dichlorophenyl)-2-hydroxy-3-nitropropanoate 在 硼烷四氢呋喃络合物 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 [2-(3,4-dichlorophenyl)-2-hydroxymethylmorpholin-4-yl]phenylmethanone
  参考文献：
  名称：

  Asymmetric Synthesis of an Antagonist of Neurokinin Receptors: SSR 241586

  摘要：

  SSR 241586 is a 2,2-disubstituted morpholine, developed by Sanofi-Aventis, which is active in the treatment of schizophrenia and irritable bowel syndrome (IBS). Different strategies have been studied to synthesize this molecule and among the strategies an organo-catalyzed Henry reaction, applied to an a.-keto ester, has produced SSR 241586 in excellent enantiomeric excess.

  DOI：

  10.1021/jo102471r
• 作为产物：
  描述：

  硝基甲烷 、 2-(3,4-二氯苯基)-2-氧代乙酸乙酯 在 O-benzoylcupreine 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以76%的产率得到(R)-ethyl 2-(3,4-dichlorophenyl)-2-hydroxy-3-nitropropanoate
  参考文献：
  名称：

  Enantioselective Synthesis of SSR 241586 by Using an Organo-Catalyzed Henry Reaction

  摘要：

  An organo-catalyzed Henry reaction, applied to an alpha-keto ester, has allowed the enantioselective synthesis of SSR 241586, a 2,2-disubstituted morpholine active in the treatment of schizophrenia and irritable bowel syndrome (IBS).

  DOI：

  10.1021/ol101555g

文献信息

• Enantioselective Synthesis of SSR 241586 by Using an Organo-Catalyzed Henry Reaction
  作者：Anne Cochi、Thomas-Xavier Métro、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/ol101555g

  日期：2010.8.20

  An organo-catalyzed Henry reaction, applied to an alpha-keto ester, has allowed the enantioselective synthesis of SSR 241586, a 2,2-disubstituted morpholine active in the treatment of schizophrenia and irritable bowel syndrome (IBS).
• Asymmetric Synthesis of an Antagonist of Neurokinin Receptors: SSR 241586
  作者：Thomas-Xavier Métro、Anne Cochi、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/jo102471r

  日期：2011.4.15

  SSR 241586 is a 2,2-disubstituted morpholine, developed by Sanofi-Aventis, which is active in the treatment of schizophrenia and irritable bowel syndrome (IBS). Different strategies have been studied to synthesize this molecule and among the strategies an organo-catalyzed Henry reaction, applied to an a.-keto ester, has produced SSR 241586 in excellent enantiomeric excess.