ethyl 4-(diisopropoxyphosphoryl)-3-phenylbut-2-enoate | 1257246-55-1

• 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: ethyl 4-(diisopropoxyphosphoryl)-3-phenylbut-2-enoate
• 英文别名: ethyl (Z)-4-di(propan-2-yloxy)phosphoryl-3-phenylbut-2-enoate
• CAS: 1257246-55-1
• 化学式: C₁₈H₂₇O₅P
• 分子量: 354.383
• InChiKey: DKQJEEIPWCBAPR-SFQUDFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(diisopropoxyphosphoryl)-3-phenylbut-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100%的产率得到ethyl 4-(diisopropoxyphosphoryl)-3-phenylbutanoate
  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：

  反-β-甲基肉桂酸乙酯 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 ethyl 4-(diisopropoxyphosphoryl)-3-phenylbut-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.