(E)-diethyl (2-(4-methoxyphenyl)but-1-en-1-yl)phosphonate | 1377154-04-5

• 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: (E)-diethyl (2-(4-methoxyphenyl)but-1-en-1-yl)phosphonate
• 英文别名: 1-[(E)-1-[diethoxy(oxido)phosphaniumyl]but-1-en-2-yl]-4-methoxybenzene
• CAS: 1377154-04-5
• 化学式: C₁₅H₂₃O₄P
• 分子量: 298.319
• InChiKey: LMIVDXJLUMNHGS-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-diethyl (2-(4-methoxyphenyl)but-1-en-1-yl)phosphonate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (Sc,Sp)-WalPhos 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、1.01 MPa 条件下， 反应 24.0h， 以98%的产率得到diethyl (2-(4-methoxyphenyl)butyl)phosphonate
  参考文献：
  名称：

  Enantioselective synthesis of optically active alkylphosphonates via Rh-catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated phosphonates

  摘要：

  The Rh-catalyzed asymmetric hydrogenation of beta-substituted alpha,beta-unsaturated phosphonates using (S-c,S-p)-WalPhos as the chiral ligand is reported, in which a wide range of optically active beta-substituted alkylphosphonates were obtained in good yields and with good to excellent enantioselectivities (86-98% ee). In contrast to the Rh/(R-c,S-a)-FAPhos system previously reported by us, the present catalytic system shows a wider substrate scope, and can perform the hydrogenation under milder reaction conditions. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.024
• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 、 对甲氧基苯丙酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以56%的产率得到(E)-diethyl (2-(4-methoxyphenyl)but-1-en-1-yl)phosphonate
  参考文献：
  名称：

  Enantioselective synthesis of optically active alkylphosphonates via Rh-catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated phosphonates

  摘要：

  The Rh-catalyzed asymmetric hydrogenation of beta-substituted alpha,beta-unsaturated phosphonates using (S-c,S-p)-WalPhos as the chiral ligand is reported, in which a wide range of optically active beta-substituted alkylphosphonates were obtained in good yields and with good to excellent enantioselectivities (86-98% ee). In contrast to the Rh/(R-c,S-a)-FAPhos system previously reported by us, the present catalytic system shows a wider substrate scope, and can perform the hydrogenation under milder reaction conditions. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.024

文献信息

• Enantioselective synthesis of optically active alkylphosphonates via Rh-catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated phosphonates
  作者：Zheng-chao Duan、Lian-zhi Wang、Xin-jian Song、Xiang-ping Hu、Zhuo Zheng

  DOI：10.1016/j.tetasy.2012.03.024

  日期：2012.4

  The Rh-catalyzed asymmetric hydrogenation of beta-substituted alpha,beta-unsaturated phosphonates using (S-c,S-p)-WalPhos as the chiral ligand is reported, in which a wide range of optically active beta-substituted alkylphosphonates were obtained in good yields and with good to excellent enantioselectivities (86-98% ee). In contrast to the Rh/(R-c,S-a)-FAPhos system previously reported by us, the present catalytic system shows a wider substrate scope, and can perform the hydrogenation under milder reaction conditions. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.