(E)-diethyl (2-(2-methoxyphenyl)prop-1-en-1-yl)phosphonate | 1200436-17-4

• 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-(2-methoxyphenyl)prop-1-en-1-yl)phosphonate
• CAS: 1200436-17-4
• 化学式: C₁₄H₂₁O₄P
• 分子量: 284.292
• InChiKey: GNCSQWHILYGMGC-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-diethyl (2-(2-methoxyphenyl)prop-1-en-1-yl)phosphonate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 1-{(R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]lpropyl}-2-(diphenylphosphino)benzimidazole 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 反应 24.0h， 以94%的产率得到
  参考文献：
  名称：

  Rh-ImiFerroPhos complexes catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated hosphonates

  摘要：

  A series of chiral ferrocenyl diphosphine ligands (ImiFerroPhos ligands) has been applied to the hydrogenation of beta-substituted alpha,beta-unsaturated phosphonates to generate a range of optically active beta-substituted alkylphosphonates in good yields with good enantioselectivity (up to 92% ee) under mild reaction conditions. (C) 2014, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s1872-2067(12)60742-6
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 亚甲基二磷酸四乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以52%的产率得到(E)-diethyl (2-(2-methoxyphenyl)prop-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