ethyl (E)-phenyl(styryl)phosphinate | 82943-05-3

• 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: ethyl (E)-phenyl(styryl)phosphinate
• 英文别名: [(E)-2-[ethoxy(phenyl)phosphoryl]ethenyl]benzene
• CAS: 82943-05-3
• 化学式: C₁₆H₁₇O₂P
• 分子量: 272.284
• InChiKey: JHOOPWSZMSPZJE-BUHFOSPRSA-N

物化性质

• 沸点：
  392.0±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯膦酰二氯 在 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.25h， 生成 ethyl (E)-phenyl(styryl)phosphinate
  参考文献：
  名称：

  Synthesis of P-chiral enephosphonic acid derivatives

  摘要：

  An efficient and convenient synthesis of chiral enephosphonic acid derivatives (enephosphonates, enephosphonamides, enephosphinates) was reported by a two-step procedure involving alkylidenediphosphorylation of nucleophiles followed by a Horner-Emmons olefination. Depending on the selected strategy, the synthesis could be executed according to a one-pot or a two-step reaction sequence. Regioselectivity of Horner-Emmons reaction and P-31-NMR study of diphosphorylated anions were described. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01889-2

文献信息

• Copper-Catalyzed C-P Coupling through Decarboxylation
  作者：Jie Hu、Ning Zhao、Bin Yang、Ge Wang、Li-Na Guo、Yong-Min Liang、Shang-Dong Yang

  DOI：10.1002/chem.201003561

  日期：2011.5.9

  developed by copper‐catalyzed decarboxylative coupling of alkenyl, alkynyl carboxylic acids, and N‐benzylproline, respectively, with R2P(O)H (see scheme). All classes of products are important precursors for preparation of biologically active molecules and various phosphorus ligands. This finding represents the first example of copper‐catalyzed decarboxylative coupling to construct CP bonds.

  膦酸：通过铜催化的烯基，炔基羧酸和N-苄基脯氨酸分别与R 2 P（O）H（参见方案）。所有种类的产品都是制备生物活性分子和各种磷配体的重要前体。这一发现表示铜催化脱羧耦合构造C的第一示例 P键。
• Copper (II)-catalyzed regio- and stereoselective addition of H/P(O)R2 to alkynes
  作者：Inna G. Trostyanskaya、Irina P. Beletskaya

  DOI：10.1016/j.tet.2014.02.037

  日期：2014.4

  catalyst for β-E regio- and stereoselective syn-addition of the H–P(O)-bond of diphenylphosphine oxide, H-phosphinates, dialkylphosphites to various alkynes in the synthesis of P(O)-containing alkenes. Without additives and ligands Cu(II)-compounds showed better results than CuI or Ni(acac)2. The catalytic system developed is tolerant to typical organic functional groups present in the alkynes and to the

  Cu（acac）2是在P（O）合成中，β- E区域和立体选择性地将二苯膦氧化物，H-次膦酸酯，二烷基亚磷酸酯的H–P（O）键加成到各种炔烃上的新型通用催化剂）的烯烃。没有添加剂和配体，Cu（II）化合物显示出比CuI或Ni（acac）2更好的结果。所开发的催化系统对炔烃中存在的典型有机官能团以及H-P（O）化合物中不同取代基的性质具有耐受性。
• Nickel-Catalyzed Decarboxylative C–P Cross-Coupling of Alkenyl Acids with P(O)H Compounds
  作者：Yile Wu、Liu Leo Liu、Kaili Yan、Pengxiang Xu、Yuxing Gao、Yufen Zhao

  DOI：10.1021/jo501321m

  日期：2014.9.5

  The first nickel-catalyzed decarboxylative C–P coupling of a wide range of alkenyl acids with various P(O)H compounds, especially for H-phosphonates, has been developed, affording a versatile and efficient tool for the preparation of valuable (E)-1-alkenylphosphonates, (E)-1-alkenylphosphinate oxides, and (E)-1-alkenylphosphine oxides with high stereoselectivity and broad substrate applicability. DFT

  已开发出首个镍催化的各种烯基酸与各种P（O）H化合物（特别是对于H膦酸酯）的脱羧C-P偶联，为制备有价值的（E）提供了一种通用而有效的工具-1- alkenylphosphonates，（ë）-1- alkenylphosphinate氧化物，和（ë）高立体选择性和广泛的底物的适用性-1- alkenylphosphine氧化物。DFT计算表明，由于亲核性强和尺寸大，在还原消除步骤中膦配体比氮配体表现出更好的催化性能。
• Efficient and Selective Nickel-Catalyzed Addition of H−P(O) and H−S Bonds to Alkynes
  作者：Li-Biao Han、Chen Zhang、Hideaki Yazawa、Shigeru Shimada

  DOI：10.1021/ja0494297

  日期：2004.4.28

  metal catalysts in the catalytic additions of a variety of P(O)-H bonds and an S-H bond to alkynes, affording regio- and stereoselectively both the Markovnikov and the anti-Markovnikov adducts, respectively, in high yields. A related five-coordinate hydrido nickel complex in the catalysis is successfully isolated, which can react readily with an alkyne to give the addition products.

  廉价的镍催化剂在催化加成各种 P(O)-H 键和 SH 键到炔烃时比相应的贵金属催化剂更具反应性，提供区域和立体选择性的马尔科夫尼科夫和反马尔科夫尼科夫加合物，分别以高产。催化剂中相关的五配位氢化镍配合物被成功分离，它可以很容易地与炔烃反应生成加成产物。
• Copper-catalyzed addition of H-phosphine oxides to alkynes forming alkenylphosphine oxides
  作者：Mingyu Niu、Hua Fu、Yuyang Jiang、Yufen Zhao

  DOI：10.1039/b613416e

  日期：——

  We have developed efficient copper-catalyzed additions of P(O)H compounds to alkynes, and the reactions provided the regio- and stereoselective E-alkenylphosphine oxides under catalysis of the commercially available and inexpensive copper catalyst system CuI/ethylenediamine. This finding is the first example of copper-catalyzed hydrophosphinylation of alkynes to synthesize alkenylphosphine oxides.

  我们开发了高效的铜催化P(O)H化合物与炔烃的加成反应，该反应在商业上可获得且廉价的铜催化剂系统CuI/乙二胺的催化下，提供了区域和立体选择性的E-烯烃基膦氧化物。该发现是铜催化炔烃氢膦化合成烯烃基膦氧化物的第一个例子。