diisopropyl (E)-(2-phenylethenyl)phosphonate | 78463-00-0

• 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 (E)-(2-phenylethenyl)phosphonate
• 英文别名: (E)-styrylphosphonic acid diisopropyl ester；(E)-diisopropyl (2-phenylvinyl)phosphonate；diisopropyl (E)-2-phenylethenylphosphonate；(E)-diisopropyl 2-phenylvinylphosphonate；(E)-diisopropyl styrylphosphonate；diisopropyl (E)-styrylphosphonate；[(E)-2-di(propan-2-yloxy)phosphorylethenyl]benzene
• CAS: 78463-00-0
• 化学式: C₁₄H₂₁O₃P
• 分子量: 268.293
• InChiKey: ZYKLRHLBIBFPEX-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diisopropyl (E)-(2-phenylethenyl)phosphonate 在 potassium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 1,3-diphenyl-1-propyne
  参考文献：
  名称：

  Synthesis of allenes by double Horner–Wadsworth–Emmons reaction

  摘要：

  LDA treatment of aldehydes or ketone with alkenylphosphonates 2, prepared by Horner-Wadsworth-Emmons (HWE) reaction of methylenebisphosphonate I with aldehydes, afforded Baylis-Hillman reaction-type products 5 in high yields. HWE olefination of 5 with KH or KH-18-crown-6 as a base provided allenes in good yields. One-flask procedure was successfully developed starting from I to afford an allene in a reasonably good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01089-4
• 作为产物：
  描述：

  diisopropyl phosphorochloridite 在 四氯化碳 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 diisopropyl (E)-(2-phenylethenyl)phosphonate
  参考文献：
  名称：

  C-甲硅烷基-P-氯亚烷基正膦与羰基化合物的反应

  摘要：

  图形摘要摘要 P-氯酰化物与羰基化合物的反应导致形成四元磷杂环——2λ5-氯-2,2-氧杂膦烷。2-氯-2,2-氧杂膦烷取决于α-原子碳上的取代基R，重排形成2-氯烷基膦酸酯（R = H、Alk、Ar）或消除三甲基氯硅烷（R = Me3Si）转化为反式-磷酸化烯烃。

  DOI：

  10.1080/10426507.2015.1054932

文献信息

• Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes
  作者：Qingwen Gui、Liang Hu、Xiang Chen、Jidan Liu、Ze Tan

  DOI：10.1039/c5cc04826e

  日期：——

  An efficient and stereoselective synthesis of vinylphosphonates and phosphine oxides was developed starting from styrenes using AgNO3 as the catalyst and K2S2O8 as the oxidant. Various vinyl-phosphonates and phosphine oxides were synthesized in good yields with excellent regioselectivity.

  从苯乙烯开始，使用AgNO 3作为催化剂，K 2 S 2 O 8作为氧化剂，开发了一种有效的立体选择性合成乙烯基膦酸酯和氧化膦的方法。以良好的产率和优异的区域选择性合成了各种乙烯基膦酸酯和氧化膦。
• 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-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。
• Experimental and theoretical studies on nickel–zinc-catalyzed cross-coupling of <i>gem</i>-dibromoalkenes with P(O)–H compounds
  作者：Liu Leo Liu、Ye Lv、Yile Wu、Xiang Gao、Zhiping Zeng、Yuxing Gao、Guo Tang、Yufen Zhao

  DOI：10.1039/c3ra45212c

  日期：——

  A new stereoselective one-pot protocol for the preparation of E-alkenyl-phosphorus compounds under catalysis of an inexpensive nickel–zinc catalyst system has been developed, which provides a potential useful method for C–P bond formation.

  一个新的立体选择性一锅法合成E-烯基磷化合物的协同催化镍-锌催化体系已经开发出来，为C-P键形成提供了潜在有用的方法。
• 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。