diisopropyl (2,2-diphenylvinyl)phosphonate | 78462-92-7

• 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: diisopropyl (2,2-diphenylvinyl)phosphonate
• 英文别名: [2-Di(propan-2-yloxy)phosphoryl-1-phenylethenyl]benzene
• CAS: 78462-92-7
• 化学式: C₂₀H₂₅O₃P
• 分子量: 344.39
• InChiKey: SGZXXHSEQQIZTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  441.5±45.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-溴-1-苯基乙烯基)苯 、 phosphoric acid triisopropyl ester; compound with copper (I)-chloride 以81%的产率得到
  参考文献：
  名称：

  AXELRAD G.; LAOSOOKSATHIT S.; ENGEL R., SYNTH. COMMUN., 1980, 10, NO 12, 933-937

  摘要：

  DOI：

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。
• Palladium-Catalyzed Addition/Cyclization of (2-Hydroxyaryl)boronic Acids with Alkynylphosphonates: Access to Phosphacoumarins
  作者：Dumei Ma、Shanshan Hu、Sirui Chen、Jiaoting Pan、Song Tu、Yingwu Yin、Yuxing Gao、Yufen Zhao

  DOI：10.1021/acs.orglett.0c03151

  日期：2020.10.16

  A facile palladium-catalyzed addition/cyclization of (2-hydroxyaryl)boronic acids with alkynylphosphonates has been developed, providing an effective strategy to construct a series of valuable phosphacoumarins. This methodology features excellent regioselectivity and broad substrate tolerance.

  已经开发了一种简便的钯催化的（2-羟基芳基）硼酸与炔基膦酸酯的加成/环化反应，为构建一系列有价值的磷香豆素提供了有效的策略。该方法具有出色的区域选择性和广泛的底物耐受性。
• Palladium‐Catalyzed Olefination of <i>N</i> ‐Tosylhydrazones as <i>β</i> ‐Diazo Phosphonate Precursors with Arylhalides
  作者：Jing He、Yijiao Feng、Fang Yang、Bin Dai、Ping Liu

  DOI：10.1002/ejoc.202000981

  日期：2020.9.30

  An efficient Pd‐catalyzed olefination of N‐tosylhydrazones as β‐diazo phosphonate precursors with aryl halides was described. A series of 2,2‐disubstituted vinylphosphonates and (2,2‐diphenylvinyl)diarylphosphine oxides were easily obtained in moderate to excellent yields.

  描述了一种高效的Pd催化的N-甲苯磺酰hydr作为β-重氮膦酸酯前体与芳基卤化物的烯化反应。可以容易地以中等到极好的收率获得一系列2,2-二取代的乙烯基膦酸酯和（2,2-二苯基乙烯基）二芳基膦氧化物。
• Mono and double Mizoroki–Heck reaction of aryl halides with dialkyl vinylphosphonates using a reusable palladium catalyst under aqueous medium
  作者：Han-Sheng Lee、Shao-Hsuan Pai、Wei-Ting Liao、Xin-Jing Yang、Fu-Yu Tsai

  DOI：10.1039/c7ra06464k

  日期：——

  reusable Pd-catalyzed mono and double Mizoroki–Heck reactions of aryl halides and dialkyl vinylphosphonates using iPr2NH as a base in aqueous medium under air were developed. For aryl iodides, the reaction could be conducted at 80 °C under a low catalyst loading (0.1–1 mol%). When aryl bromides were applied, however, a greater amount of catalyst (5 mol%) and a longer reaction time at 120 °C were required.

  使用i Pr 2操作简单且可重复使用的Pd催化的芳基卤化物和乙烯基乙烯基膦酸二烷基酯的单和双Mizoroki-Heck反应在空气中在水性介质中开发了以NH为碱的物质。对于芳基碘化物，该反应可以在80°C的低催化剂负载量（0.1-1 mol％）下进行。然而，当使用芳基溴化物时，需要更大量的催化剂（5mol％）和更长的在120℃下的反应时间。简单地改变乙烯基二膦酸二烷基酯作为限制剂就可以高收率地形成2，2-二芳基乙烯基膦酸。反应后，残留的水溶液可重复用于Mizoroki-Heck单反应和双反应，使反应更绿色，并减少贵金属的浪费，并使用有害的有机溶剂作为反应介质。