(E)-diethyl (2-(3-methoxyphenyl)prop-1-en-1-yl)phosphonate | 1200436-18-5

• 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-(3-methoxyphenyl)prop-1-en-1-yl)phosphonate
• 英文别名: diethyl (E)-(2-(3-methoxyphenyl)prop-1-en-1-yl)phosphonate；1-[(E)-1-diethoxyphosphorylprop-1-en-2-yl]-3-methoxybenzene
• CAS: 1200436-18-5
• 化学式: C₁₄H₂₁O₄P
• 分子量: 284.292
• InChiKey: CIFJLLWJUGGPRC-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-diethyl (2-(3-methoxyphenyl)prop-1-en-1-yl)phosphonate 在 polymethylhydrosiloxane 、 copper(II) acetate monohydrate 、 (S)-(-)-5,5-双(二苯膦基)-4,4-双-1,3-苯并间二氧杂环戊烯 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 以57%的产率得到1-[(2S)-1-diethoxyphosphorylpropan-2-yl]-3-methoxybenzene
  参考文献：
  名称：

  Cu-catalyzed asymmetric conjugate reduction of β-substituted α,β-unsaturated phosphonates: an efficient synthesis of optically active β-stereogenic alkylphosphonates

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.09.094
• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 、 3-甲氧基苯乙酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 生成 (E)-diethyl (2-(3-methoxyphenyl)prop-1-en-1-yl)phosphonate
  参考文献：
  名称：

  通过Rh/f-spiroPhos催化β,β-二取代不饱和膦酸酯的不对称氢化反应选择性合成手性膦酸酯

  摘要：

  首次实现了β,β-二芳基不饱和膦酸酯的不对称氢化，用于在Rh-( R , R )-f-spiroPhos 络合物催化下合成具有优异对映选择性（高达99.9% ee）的β,β-二芳基手性膦酸酯. 此外，该催化剂对 β-芳基-β-烷基不饱和膦酸酯也表现出相当优异的性能，提供相应的手性膦酸酯，其 ee 值高达 99.9%。这种方法为不对称合成手性膦酸盐提供了一种直接的途径。

  DOI：

  10.1021/acs.joc.1c01397

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.
• Ag(I)-catalyzed synthesis of (E)-alkenyl phosphonates by oxidative coupling of H-phosphites with β-nitroolefins
  作者：Li Ma、Shengjie Shang、Hua Yuan、Yue Zhang、Zhigang Zeng、Yunfeng Chen

  DOI：10.1016/j.tetlet.2021.153530

  日期：2021.12