膦酸,(2-苯基-1-戊烯基)-,二乙基酯,(E)- | 157690-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 膦酸,(2-苯基-1-戊烯基)-,二乙基酯,(E)-
• 英文名称: diethyl (E)-2-phenyl-pent-1-enylphosphonate
• 英文别名: (E)-diethyl (2-phenylpent-1-en-1-yl)phosphonate；[(E)-1-diethoxyphosphorylpent-1-en-2-yl]benzene
• CAS: 157690-42-1
• 化学式: C₁₅H₂₃O₃P
• 分子量: 282.32
• InChiKey: SSNLGBSZXZRKNI-FYWRMAATSA-N

物化性质

• 沸点：
  374.4±25.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  膦酸,(2-苯基-1-戊烯基)-,二乙基酯,(E)- 在 ammonium hydroxide 、 四丁基硫酸氢铵 、 peroxomonosulfate(1-) 作用下， 以 甲醇 、 丁酮 为溶剂， 反应 192.0h， 生成 ethyl-1-formyl-1-phenylbutylphosphonate
  参考文献：
  名称：

  Unexpected Rearrangement of Diethyl (±)(S,S)-1,2-epoxy-2-Phenylpentylphosphonate by NH 3(aqu.) : An Easy Entry to Ethyl 1-Formyl-1-Phenylbutylphosphonate

  摘要：

  A simple reaction of diethyl (+/-)(SS)-1,2-epoxy-2-phenylpentylphosphonate with 28% NH3(aqu.) in MeOH led to the ethyl 1-formyl-1-phenylbutylphosphonate in excellent yield. The procedure consists simply in stirring the substrate and 28% NH3(aqu.) in MeOH, at 40degreesC.

  DOI：

  10.1080/10426500211733
• 作为产物：
  描述：

  diethyl pent-1-ynylphosphonate 在 5% Pd/CaCO3 喹啉 、 氢气 、 copper(l) chloride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 8.0h， 生成 膦酸,(2-苯基-1-戊烯基)-,二乙基酯,(E)-
  参考文献：
  名称：

  乙烯基膦酸酯的简便和立体选择性合成

  摘要：

  从容易获得的烷基-1-炔基膦酸酯开始，已经开发出了立体选择性合成单，二和三取代的烷基-1-烯基膦酸酯的方法，该方法是使用催化加氢或在三键上加铜盐。

  DOI：

  10.1016/s0022-328x(96)06646-6

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.
• Rh-ImiFerroPhos complexes catalyzed asymmetric hydrogenation of β-substituted α,β-unsaturated hosphonates
  作者：Zhengchao Duan、Lianzhi Wang、Xiaoyu Zuo、Xiangping Hu、Zhuo Zheng

  DOI：10.1016/s1872-2067(12)60742-6

  日期：2014.2

  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.
• Cu-catalyzed asymmetric conjugate reduction of β-substituted α,β-unsaturated phosphonates: an efficient synthesis of optically active β-stereogenic alkylphosphonates
  作者：Zheng-Chao Duan、Xiang-Ping Hu、Dao-Yong Wang、Sai-Bo Yu、Zhuo Zheng

  DOI：10.1016/j.tetlet.2009.09.094

  日期：2009.12

  A series of chiral alkylphosphonates bearing beta-stereogenic center were synthesized in good enantioselectivities (up to 95% ee) via the CuH-catalyzed asymmetric conjugate reduction of beta-substituted alpha,beta-unsaturated phosphonates under optimal conditions using Cu(OAc)(2)center dot H2O as the copper source, (R)-SEGPHOS as the ligand. PMHS as the siloxane, and t-BuOH as the additive. (C) 2009 Elsevier Ltd. All rights reserved.
• A convenient stereoselective synthesis of disubstituted alk-1-enyl phosphonates
  作者：Henri-Jean Cristau、Marie-Bénédicte Gasc、Xavier Yangkou Mbianda

  DOI：10.1016/0022-328x(94)84075-x

  日期：1994.7

  A stereoselective synthesis of disubstituted diethyl alk-1-enylphosphonates has been developed via syn addition of RMgX/CuCl to alk-1-inylphosphonates.
• Dioxirane oxidation of substituted vinylphosphonates: a novel efficient route to 1,2-epoxyalkylphosphonates
  作者：Henri-Jean Cristau、Xavier Yangkou Mbianda、Annabelle Geze、Yves Beziat、Marie-Bénédicte Gasc

  DOI：10.1016/s0022-328x(98)00856-0

  日期：1998.12

  A new stereoselective route to substituted 1,2-epoxyalkylphosphonates through oxidation of corresponding alk-1-enylphosphonates by 'in situ' generated ethylmethyldioxirane is described. (C) 1998 Elsevier Science S.A. All rights reserved.