(Z)-diisopropyl styrylphosphonate | 76371-53-4

• 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: (Z)-diisopropyl styrylphosphonate
• 英文别名: Diisopropyl (Z)-1-propenylphosphonate；[(Z)-2-di(propan-2-yloxy)phosphorylethenyl]benzene
• CAS: 76371-53-4
• 化学式: C₁₄H₂₁O₃P
• 分子量: 268.293
• InChiKey: ZYKLRHLBIBFPEX-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  亚磷酸二异丙酯 、 (Z)-β-bromostyrene 在 四(三苯基膦)钯 、 三乙胺 作用下， 反应 12.0h， 以81%的产率得到(Z)-diisopropyl styrylphosphonate
  参考文献：
  名称：

  钯催化形成新的碳-磷键

  摘要：

  二烷基芳基膦酸酯是在三乙胺存在下通过芳基溴化物与亚磷酸二烷基酯的钯催化反应制备的。乙烯基溴化物的类似处理可立体选择性地得到乙烯基膦酸二烷基酯。

  DOI：

  10.1246/bcsj.55.909

文献信息

• Copper-mediated cross-coupling of 1,1-dibromo-1-alkenes with dialkyl phosphites: a convenient synthesis of 1-alkenylphosphonates
  作者：Gwilherm Evano、Krishnaji Tadiparthi、François Couty

  DOI：10.1039/c0cc01617a

  日期：——

  An efficient and stereoselective procedure for the preparation of E-1-alkenylphosphonates by copper-mediated cross-coupling between 1,1-dibromo-1-alkenes and dialkyl phosphites is reported. The reaction allows for formal substitution of both bromine atoms, respectively, by an hydrogen and a dialkoxyphosphoryl.

  报道了一种通过铜介导的1，1-二溴-1-烯与亚磷酸二烷基酯的交叉偶联制备E-1-烯基膦酸酯的有效和立体选择性的方法。该反应允许两个溴原子分别被氢和二烷氧基磷酰基正式取代。
• Copper-Mediated Selective Cross-Coupling of 1,1-Dibromo-1-alkenes and Heteronucleophiles: Development of General Routes to Heterosubstituted Alkynes and Alkenes
  作者：Kévin Jouvin、Alexis Coste、Alexandre Bayle、Frédéric Legrand、Ganesan Karthikeyan、Krishnaji Tadiparthi、Gwilherm Evano

  DOI：10.1021/om3005614

  日期：2012.11.26

  site-selective, double, or alkynylative cross-coupling, therefore providing divergent and straightforward entries to numerous building blocks such as bromoenamides, ynamides, ketene N,N-acetals, bromoenol ethers, ynol ethers, ketene O,O-acetals, or vinylphosphonates and further expanding the copper catalysis toolbox with useful and versatile processes.

  据报道，有效的和通用的程序是将1，1-二溴代烯烃与N-，O-和P-亲核试剂进行交叉偶联。反应条件的微调允许位点选择性，双重或炔基交叉偶联，因此为许多结构单元（如溴酰胺，乙酰胺，乙烯酮N，N-乙缩醛，溴烯醇醚，炔醇醚）提供了分散而直接的入口，乙烯酮O，O-乙缩醛或乙烯基膦酸酯，并通过有用的通用方法进一步扩展了铜催化工具箱。
• Nickel(II)-Magnesium-Catalyzed Cross-Coupling of 1,1-Dibromo-1-alkenes with Diphenylphosphine Oxide: One-Pot Synthesis of (<i>E</i>)-1-Alkenylphosphine Oxides or Bisphosphine Oxides
  作者：Liu Liu、Yulei Wang、Zhiping Zeng、Pengxiang Xu、Yuxing Gao、Yingwu Yin、Yufen Zhao

  DOI：10.1002/adsc.201200853

  日期：2013.3.11

  A novel nickel(II)‐magnesium‐mediated cross‐coupling of diphenylphosphine oxide with a variety of 1,1‐dibromo‐1‐alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)‐1‐alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic

  已开发出新颖的镍（II）-镁介导的二苯基膦氧化物与各种1,1-二溴-1-烯的交叉偶联反应，为各种（E）-的立体选择性合成提供了强大而通用的方法1-烯基氧化膦或双氧化膦，操作简便，具有良好的高收率和广泛的底材适用性。机理研究表明，该反应可能涉及Hirao还原，交叉偶联和Michael加成。
• A new synthesis of π-electron conjugated phosphonates and phosphonic bis(diethylamides) and their SHG activities
  作者：Takuji Ogawa、Naoya Usuki、Noboru Ono

  DOI：10.1039/a709082j

  日期：——

  A series of vinylic and arylic phosphonates and phosphonic bis(diethylamides) were prepared by copper promoted substitution of the corresponding bromides. These π-electron conjugated phosphonates and phosphonic bis(diethylamides) were investigated to elucidate their optical and second harmonic generation (SHG) properties; it was found that diphenyl 2-(4-dimethylaminophenyl)ethenylphosphonate exhibited strong SHG activity, the efficiency being 13 times greater than that of urea.

  通过铜催化的相应溴化物的取代反应，制备了一系列乙烯基和芳基膦酸盐及双（二乙基酰胺）膦酸。研究了这些共轭的磷酸盐和双（二乙基酰胺）膦酸的光学性质和二次谐波产生（SHG）特性；发现二苯基2-（4-二甲氨基苯基）乙烯基膦酸盐具有强烈的SHG活性，效率比尿素高13倍。
• Stereoselective synthesis of vinylphosphonate
  作者：Toshikazu Hirao、Toshio Masunaga、Yoshiki Ohshiro、Toshio Agawa

  DOI：10.1016/0040-4039(80)80245-0

  日期：1980.1

  Dialkyl vinylphosphonate is stereoselectively prepared by palladium-catalyzed reaction of vinyl bromide with dialkyl phosphite.

  乙烯基膦酸二烷基酯是通过钯催化的乙烯基溴与亚磷酸二烷基酯的立体选择制备的。