(S)-diethyl 1-(naphthalen-1-yl)-3-oxo-3-phenylpropylphosphonate | 1156004-89-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-diethyl 1-(naphthalen-1-yl)-3-oxo-3-phenylpropylphosphonate
• 英文别名: diethyl (S)-1-(naphthalen-1-yl)-3-oxo-3-phenylpropylphosphonate；(3S)-3-[diethoxy(oxido)phosphaniumyl]-3-naphthalen-1-yl-1-phenylpropan-1-one
• CAS: 1156004-89-5
• 化学式: C₂₃H₂₅O₄P
• 分子量: 396.423
• InChiKey: PQWNZQIYPSAPOK-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二乙基亚磷酸氢酯 、 3-(naphthalen-1-yl)-1-phenylprop-2-en-1-one 在 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine 、 [Yb(bis(trimethylsilyl)amido)3(μ-Cl)Li(tetrahydrofuran)3] 作用下， 以 甲苯 为溶剂， 反应 26.33h， 以87%的产率得到(S)-diethyl 1-(naphthalen-1-yl)-3-oxo-3-phenylpropylphosphonate
  参考文献：
  名称：

  Chiral ytterbium silylamide catalyzed enantioselective phospha-Michael addition of diethyl phosphite to chalcones

  摘要：

  An efficient and enantioselective phospha-Michael addition of diethyl phosphite to chalcones has been established. In the presence of a catalytic amount of chiral lanthanide silylamide generated from [(Me3Si)(2)N](3)Yb(mu-Cl)Li(THF)(3) and salen, the reaction produced the target gamma-oxophosphonates with high yields and enantioselectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.06.008

文献信息

• Highly Enantioselective 1,4-Addition of Diethyl Phosphite to Enones Using a Dinuclear Zn Catalyst
  作者：Depeng Zhao、Ye Yuan、Albert S. C. Chan、Rui Wang

  DOI：10.1002/chem.200802688

  日期：2009.3.9

  Zinc benefits: The first catalytic asymmetric phospha‐Michael addition of enones has been developed. Under mild reaction conditions, the γ‐oxo phosphonates could be obtained in high yields (up to 99 %) with excellent enantioselectivities (93–99 % ee; see scheme). The strategy makes the asymmetric synthesis of biologically important phosphonate compounds more accessible.

  锌的优点：首次开发了烯酮的催化不对称磷酸-迈克尔加成反应。在温和的反应条件下，可以以高收率（高达99％）和出色的对映选择性（93–99％ee；参见方案）获得γ-氧代膦酸酯。该策略使生物学上重要的膦酸酯化合物的不对称合成更容易实现。
• Chiral ytterbium silylamide catalyzed enantioselective phospha-Michael addition of diethyl phosphite to chalcones
  作者：Guoyao Li、Lu Wang、Zhigang Yao、Fan Xu

  DOI：10.1016/j.tetasy.2014.06.008

  日期：2014.7

  An efficient and enantioselective phospha-Michael addition of diethyl phosphite to chalcones has been established. In the presence of a catalytic amount of chiral lanthanide silylamide generated from [(Me3Si)(2)N](3)Yb(mu-Cl)Li(THF)(3) and salen, the reaction produced the target gamma-oxophosphonates with high yields and enantioselectivity. (C) 2014 Elsevier Ltd. All rights reserved.