(E)-(4-nitro)styryl diphenylphosphine oxide | 82943-01-9

• 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: (E)-(4-nitro)styryl diphenylphosphine oxide
• 英文别名: 1-[(E)-2-diphenylphosphorylethenyl]-4-nitrobenzene
• CAS: 82943-01-9
• 化学式: C₂₀H₁₆NO₃P
• 分子量: 349.326
• InChiKey: QWEABZLIBVIUSN-FOCLMDBBSA-N

物化性质

• 熔点：
  162-163 °C
• 沸点：
  550.8±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(E)-2-(4-Nitro-phenyl)-vinyl]-diphenyl-phosphane 在 双氧水 作用下， 以 丙酮 为溶剂， 以73.8%的产率得到(E)-(4-nitro)styryl diphenylphosphine oxide
  参考文献：
  名称：

  Gloyna, Dieter, Journal fur praktische Chemie (Leipzig 1954), 1984, vol. 326, # 3, p. 360 - 366

  摘要：

  DOI：

文献信息

• Knoevenagel Condensation of Phosphinoylacetic Acids with Aldehydes: An Efficient One-Pot Strategy for the Synthesis of P-Functionalized Alkenyl Compounds
  作者：Kamil Dziuba、Katarzyna Szwaczko、Sławomir Frynas

  DOI：10.1055/s-0040-1705993

  日期：2021.6

  phosphinoylacetic acids derived from P(O)–H compounds were used as the starting materials in the reaction, providing a highly stereoselective and efficient method for constructing α,β-unsaturated phosphine oxides. Moreover, this simple and practical procedure provides an alternative and more environmentally friendly synthesis strategy for this type of P-functionalized alkenyl compounds.

  各种各样的可商购的醛已被用于Knoevenagel缩合反应，以得到E-烯基氧化膦和乙烯基氧化膦。衍生自P（O）–H化合物的随时可用的膦酰基乙酸用作反应的起始原料，为构建α，β-不饱和氧化膦提供了高度立体选择性和有效的方法。而且，这种简单而实用的方法为此类P-官能化的烯基化合物提供了另一种更环保的合成策略。
• Copper-catalyzed stereo- and regioselective hydrophosphorylation of terminal alkynes: scope and mechanistic study
  作者：Junchen Li、Zhenhua Gao、Yongbiao Guo、Haibo Liu、Peichao Zhao、Xiaojing Bi、Enxue Shi、Junhua Xiao

  DOI：10.1039/d2ra02908a

  日期：——

  highly stereo- and regioselective hydrophosphorylation of terminal alkynes to E-alkenylphosphorus compounds was well developed. It represents a general and practical hydrophosphorylation method, of which diarylphosphine oxide, dialkylphosphine oxide and dialkyl phosphite all had effective P(O)H parts to react with different types of terminal alkynes. Contrary to previous air-sensitive reports, all the reactions

  在这里，铜催化的末端炔烃到 E-烯基磷化合物的高度立体和区域选择性氢化磷酸化的协议得到了很好的发展。它代表了一种通用且实用的氢化磷酸化方法，其中二芳基氧化膦、二烷基氧化膦和亚磷酸二烷基酯均具有有效的P(O)H部分与不同类型的末端炔烃反应。与之前对空气敏感的报道相反，所有反应都在空气中进行。由于某些天然产物衍生物和市售除草剂的高立体选择性和区域选择性、良好的官能团耐受性、可扩展性和易于后期衍生化，这种方法非常有吸引力。更重要的是，
• Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes
  作者：Jun-Long Zhan、Bing-Jie Wang、Chen-Xi Wang、Xin-Ming Zhao、Sai-Nan Zhou、Zao-Zao Dou、Xin-Xin Yang、Lin Zhu、Wei Ren

  DOI：10.1039/d3ob00607g

  日期：——

  An efficient, practical and regioselective synthesis of (E)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and

  在铜催化和 4-HO-TEMPOH 氧化下，以烯烃为原料，开发了一种高效、实用和区域选择性合成 ( E )-烯基氧化膦的方法。初步的机理研究清楚地表明膦酰基自由基参与了这一过程。此外，该方法具有反应条件温和、官能团耐受性好、区域选择性优良等特点，有望有效用于药物分子骨架的后期功能化。该反应将为合成复杂的含磷生物活性分子创造机会。
• Copper-Catalyzed Decarboxylative C–P Cross-Coupling of Alkynyl Acids with <i>H</i>-Phosphine Oxides: A Facile and Selective Synthesis of (<i>E</i>)-1-Alkenylphosphine Oxides
  作者：Gaobo Hu、Yuxing Gao、Yufen Zhao

  DOI：10.1021/ol502009b

  日期：2014.9.5

  A novel and efficient copper-catalyzed decarboxylative cross-coupling of alkynyl acids for the stereoselective synthesis of E-alkenylphosphine oxides has been developed. In the presence of 10 mol % of CuCl without added ligand, base, and additive, various alkynyl acids reacted with H-phosphine oxides to afford E-alkenylphosphine oxides with operational simplicity, broad substrate scope, and the stereoselectivity for E-isomers.
• GLOYNA, D., J. PRAKT. CHEM., 1984, 326, N 3, 360-366
  作者：GLOYNA, D.

  DOI：——

  日期：——