methyl 4-(dimethoxyphosphoryl)-3-(4-nitrophenyl)but-2-enoate | 1257246-64-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 4-(dimethoxyphosphoryl)-3-(4-nitrophenyl)but-2-enoate
• 英文别名: methyl (Z)-4-dimethoxyphosphoryl-3-(4-nitrophenyl)but-2-enoate
• CAS: 1257246-64-2
• 化学式: C₁₃H₁₆NO₇P
• 分子量: 329.246
• InChiKey: ORLYLXJRUJWQPY-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-(dimethoxyphosphoryl)-3-(4-nitrophenyl)but-2-enoate 在 (S)-(-)-5,5-双(二苯膦基)-4,4-双-1,3-苯并间二氧杂环戊烯 、 copper(II) acetate monohydrate 、 叔丁醇 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以95%的产率得到(-)-methyl 4-(dimethoxyphosphoryl)-3-(4-nitrophenyl)butanoate
  参考文献：
  名称：

  An enantioselective synthesis of 3-aryl-4-phosphonobutyric acid esters via Cu-catalyzed asymmetric conjugate reduction

  摘要：

  The asymmetric conjugate reduction of 3-aryl-4-phosphonobutenoates has been demonstrated which provides an enantioselective synthesis of optically active 3-aryl-4-phosphonobutyric acid esters. A wide range of 3-aryl-4-phosphonobutenoate derivates are reduced with high enantioselectivities (up to 94% ee) using an (S)-Segphos/Cu(OAc)(2)center dot H2O catalyst system (1 or 5 mol %) in the presence of PMHS and t-BuOH. The reduction is influenced by the steric and electronic effects of the substrates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.12.009
• 作为产物：
  描述：

  methyl (E)-3-(p-nitrophenyl)-2-butenoate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 13.0h， 生成 methyl 4-(dimethoxyphosphoryl)-3-(4-nitrophenyl)but-2-enoate
  参考文献：
  名称：

  Enantioselective Rh-Catalyzed Hydrogenation of 3-Aryl-4-phosphonobutenoates with a P-Stereogenic BoPhoz-Type Ligand

  摘要：

  A series of chiral 3-aryl-4-phosphonobutyric acid esters were synthesized in high enantioselectivities (93-98% ee) via the Rh-catalyzed asymmetric hydrogenation of the corresponding 3-aryl-4-phosphonobutenoates using a P-stereogenic BoPhoz-type phosphine-aminophosphine ligand. The methodology has been successfully applied to the asymmetric synthesis of a potential GABA(B) antagonist, (R)-phaclofen, in high enantioselectivity.

  DOI：

  10.1021/jo101849b

文献信息

• Enantioselective Rh-Catalyzed Hydrogenation of 3-Aryl-4-phosphonobutenoates with a <i>P</i>-Stereogenic BoPhoz-Type Ligand
  作者：Zheng-Chao Duan、Xiang-Ping Hu、Cheng Zhang、Zhuo Zheng

  DOI：10.1021/jo101849b

  日期：2010.12.3

  A series of chiral 3-aryl-4-phosphonobutyric acid esters were synthesized in high enantioselectivities (93-98% ee) via the Rh-catalyzed asymmetric hydrogenation of the corresponding 3-aryl-4-phosphonobutenoates using a P-stereogenic BoPhoz-type phosphine-aminophosphine ligand. The methodology has been successfully applied to the asymmetric synthesis of a potential GABA(B) antagonist, (R)-phaclofen, in high enantioselectivity.
• An enantioselective synthesis of 3-aryl-4-phosphonobutyric acid esters via Cu-catalyzed asymmetric conjugate reduction
  作者：Wei-Lei Guo、Chuan-Jin Hou、Zheng-Chao Duan、Xiang-Ping Hu

  DOI：10.1016/j.tetasy.2011.12.009

  日期：2011.12

  The asymmetric conjugate reduction of 3-aryl-4-phosphonobutenoates has been demonstrated which provides an enantioselective synthesis of optically active 3-aryl-4-phosphonobutyric acid esters. A wide range of 3-aryl-4-phosphonobutenoate derivates are reduced with high enantioselectivities (up to 94% ee) using an (S)-Segphos/Cu(OAc)(2)center dot H2O catalyst system (1 or 5 mol %) in the presence of PMHS and t-BuOH. The reduction is influenced by the steric and electronic effects of the substrates. (C) 2012 Elsevier Ltd. All rights reserved.