diethyl (E)-(2-(thiophen-2-yl)prop-1-en-1-yl)phosphonate | 1182848-38-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (E)-(2-(thiophen-2-yl)prop-1-en-1-yl)phosphonate
• 英文别名: (E)-diethyl 2-(thiophen-2-yl)prop-1-enylphosphonate；diethyl (E)-(2-thienyl-1-propene)phosphonate；(E)-diethyl (2-(thiophen-2-yl)prop-1-en-1-yl)phosphonate；2-[(E)-1-diethoxyphosphorylprop-1-en-2-yl]thiophene
• CAS: 1182848-38-9
• 化学式: C₁₁H₁₇O₃PS
• 分子量: 260.294
• InChiKey: WCKRUOCHPOQUQH-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (E)-(2-(thiophen-2-yl)prop-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-(thiophen-2-yl)propyl)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：

  2-乙酰基噻吩 、 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41%的产率得到diethyl (E)-(2-(thiophen-2-yl)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

文献信息

• Enantioselective Synthesis of Optically Active Alkanephos- phonates<i>via</i>Rhodium-Catalyzed Asymmetric Hydrogenation of β-Substituted α,β-Unsaturated Phosphonates with Ferrocene-Based Monophosphoramidite Ligands
  作者：Zheng-Chao Duan、Xiang-Ping Hu、Dao-Yong Wang、Jia-Di Huang、Sai-Bo Yu、Jun Deng、Zhuo Zheng

  DOI：10.1002/adsc.200800388

  日期：2008.9.5

  series of chiral β-substituted alkanephosphonates was synthesized in high enantioselectivities via the first rhodium-catalyzed asymmetric hydrogenation of the corresponding β-substituted-α,β-unsaturated phosphonates using a ferrocene-derived monophosphoramidite ligand, with which up to 99.5% ee have been achieved for the hydrogenation of (E)-substrates and 98.0% ee for (Z)-substrates.

  一系列手性β取代alkanephosphonates的是在高对映选择性合成经由相应的β取代-α的第一铑催化的不对称氢化，β不饱和膦酸酯用二茂铁衍生monophosphoramidite配体，利用该高达99.5％ee值有无（E）底物的氢化反应达到了氢化，（Z）底物的氢化反应达到了98.0％ee。
• 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
• Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands
  作者：Takashi Konno、Kenta Shimizu、Kenichi Ogata、Shin-ichi Fukuzawa

  DOI：10.1021/jo300129m

  日期：2012.4.6

  Newly developed ClickFerrophos II ligands were applied in the hydrogenation of alpha,beta-unsaturated phosphonates. The use of a rhodium/ClickFerrophos II catalyst was examined in the hydrogenation of fimctionalized alpha,beta-unsaturated phosphonates and was revealed to be effective for beta-alkyl-beta-aryl or beta-dialkyl phosphonates, (Z)-beta-enolester phosphonates, and alpha-phenylethenyl phosphonates, producing the corresponding chiral phosphonates in good yields with high enantioselectivities (up to 96% ee).