diethyl (E)-((3,4-dihydronaphthalen-1(2H)-ylidene)methyl)phosphonate | 1377154-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: diethyl (E)-((3,4-dihydronaphthalen-1(2H)-ylidene)methyl)phosphonate
• 英文别名: (E)-diethyl (2,3-dihydronaphthalen-4(1H)-ylidene)methylphosphonate；(4E)-4-[[diethoxy(oxido)phosphaniumyl]methylidene]-2,3-dihydro-1H-naphthalene
• CAS: 1377154-05-6
• 化学式: C₁₅H₂₁O₃P
• 分子量: 280.304
• InChiKey: ICCOWROKWGCJHG-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  41.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl (E)-((3,4-dihydronaphthalen-1(2H)-ylidene)methyl)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99%的产率得到diethyl ((1,2,3,4-tetrahydronaphthalen-1-yl)methyl)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 、 3,4-二氢-1(2H)-萘酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以22%的产率得到diethyl (E)-((3,4-dihydronaphthalen-1(2H)-ylidene)methyl)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

• 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
• 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.