methyl 4-(dimethoxyphosphoryl)-3-(2-thienyl)but-2-enoate | 1257246-66-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-(dimethoxyphosphoryl)-3-(2-thienyl)but-2-enoate
• 英文别名: methyl (E)-4-dimethoxyphosphoryl-3-thiophen-2-ylbut-2-enoate
• CAS: 1257246-66-4
• 化学式: C₁₁H₁₅O₅PS
• 分子量: 290.277
• InChiKey: XZELPHCXWWAGSW-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-(dimethoxyphosphoryl)-3-(2-thienyl)but-2-enoate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 C₄₃H₃₅F₆FeNP₂ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、6.0 MPa 条件下， 反应 24.0h， 以97%的产率得到methyl 4-(dimethoxyphosphoryl)-3-(2-thienyl)butanoate
  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
• 作为产物：
  描述：

  methyl (E)-3-(thiophen-2-yl)but-2-enoate 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-(2-thienyl)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

• 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.
• 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.