ethyl 4-(3-bromophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate | 1262022-90-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: ethyl 4-(3-bromophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate
• CAS: 1262022-90-1
• 化学式: C₁₂H₁₂BrNO₅
• 分子量: 330.135
• InChiKey: ZHPBXDHPOUYGKL-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)glutaric anhydride 、 ethyl 4-(3-bromophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate 在 三乙烯二胺 作用下， 以 氯仿 为溶剂， 生成 5-(((E)-1-ethoxy-3-nitro-1-oxo-4-(3-bromophenyl)but-3-en-2-yl)oxy)-5-oxo-3-(4-methoxyphenyl)pentanoic acid
  参考文献：
  名称：

  Organocatalytic Kinetic Resolution of Racemic Secondary Nitroallylic Alcohols Combined with Simultaneous Desymmetrization of Prochiral Cyclic Anhydrides

  摘要：

  This study describes an organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols (2) combined with simultaneous desymmetrization of prochiral cyclic anhydrides (1). The experimental results revealed that enantioselective alcoholysis of 3-substituted glutaric anhydrides afforded hemiesters (3) with high levels of enantioselectivities (up to 99% ee) in the presence of cinchonidine-derived thiourea catalyst (IV). The highly optical enrichment (up to 95% ee) of (S)-nitroallylic alcohols (2) was recovered.

  DOI：

  10.1021/jo501882q
• 作为产物：
  描述：

  乙醛酸乙酯 、 3-bromo-β-nitro-styrene 在 4-二甲氨基吡啶 、 C₁₅H₁₀F₆N₂OS 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以75%的产率得到ethyl 4-(3-bromophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate
  参考文献：
  名称：

  An efficient Morita–Baylis–Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives

  摘要：

  An efficient thiourea promoted MBH reaction of various conjugated nitroalkenes with ethyl glyoxylate was developed. The desired multifunctional products, 2-hydroxy-3-nitro-4-aryl/alkylbut-3-enoate derivatives were obtained in good to high chemical yields (56-92%) with DMAP (20 mol%) under solvent-free conditions or imidazole (100 mol%) in the presence of water. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.061

文献信息

• Organocatalytic Kinetic Resolution of Racemic Secondary Nitroallylic Alcohols Combined with Simultaneous Desymmetrization of Prochiral Cyclic Anhydrides
  作者：Suparna Roy、Kan-Fu Chen、Ramani Gurubrahamam、Kwunmin Chen

  DOI：10.1021/jo501882q

  日期：2014.10.3

  This study describes an organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols (2) combined with simultaneous desymmetrization of prochiral cyclic anhydrides (1). The experimental results revealed that enantioselective alcoholysis of 3-substituted glutaric anhydrides afforded hemiesters (3) with high levels of enantioselectivities (up to 99% ee) in the presence of cinchonidine-derived thiourea catalyst (IV). The highly optical enrichment (up to 95% ee) of (S)-nitroallylic alcohols (2) was recovered.
• An efficient Morita–Baylis–Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives
  作者：Hsuan-Hao Kuan、Raju Jannapu Reddy、Kwunmin Chen

  DOI：10.1016/j.tet.2010.10.061

  日期：2010.12

  An efficient thiourea promoted MBH reaction of various conjugated nitroalkenes with ethyl glyoxylate was developed. The desired multifunctional products, 2-hydroxy-3-nitro-4-aryl/alkylbut-3-enoate derivatives were obtained in good to high chemical yields (56-92%) with DMAP (20 mol%) under solvent-free conditions or imidazole (100 mol%) in the presence of water. (C) 2010 Elsevier Ltd. All rights reserved.