((3-bromophenyl)ethynyl)diphenylphosphine oxide | 1510838-18-2

• 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: ((3-bromophenyl)ethynyl)diphenylphosphine oxide
• 英文别名: 1-Bromo-3-(2-diphenylphosphorylethynyl)benzene；1-bromo-3-(2-diphenylphosphorylethynyl)benzene
• CAS: 1510838-18-2
• 化学式: C₂₀H₁₄BrOP
• 分子量: 381.208
• InChiKey: QXYPQJYWVXIFRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((4-methoxyphenyl)ethynyl)diphenylphosphine oxide 、 ((3-bromophenyl)ethynyl)diphenylphosphine oxide 在 potassium tert-butylate 、 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.0h， 以72%的产率得到3-(4-methoxyphenylethynyl)phenylethynyldiphenylphosphine oxide
  参考文献：
  名称：

  One-Pot Transformation of Ph₂P(O)-Protected Ethynes: Deprotection Followed by Transition Metal-Catalyzed Coupling

  摘要：

  Ph2P(O)-protected ethynes were successfully transformed to arylethynes in one-pot manner through t-BuOK-catalyzed deprotection followed by Sonogashira coupling with aryl halide. The arylethynes were obtained similarly by Ph2P(O)-deprotection, stannylation of the resulting terminal ethynes, and Migita-Kosugi-Stille coupling. Deprotection followed by intramolecular Eglinton coupling could be carried out in one-pot to provide cyclic butadiynes.

  DOI：

  10.1021/jo402176w
• 作为产物：
  描述：

  乙炔基(二苯基)膦 在 copper(l) iodide 、 四(三苯基膦)钯 、 双氧水 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 ((3-bromophenyl)ethynyl)diphenylphosphine oxide
  参考文献：
  名称：

  One-Pot Transformation of Ph₂P(O)-Protected Ethynes: Deprotection Followed by Transition Metal-Catalyzed Coupling

  摘要：

  Ph2P(O)-protected ethynes were successfully transformed to arylethynes in one-pot manner through t-BuOK-catalyzed deprotection followed by Sonogashira coupling with aryl halide. The arylethynes were obtained similarly by Ph2P(O)-deprotection, stannylation of the resulting terminal ethynes, and Migita-Kosugi-Stille coupling. Deprotection followed by intramolecular Eglinton coupling could be carried out in one-pot to provide cyclic butadiynes.

  DOI：

  10.1021/jo402176w

文献信息

• Additive-free coupling of bromoalkynes with secondary phosphine oxides to generate alkynylphosphine oxides in acetic anhydride
  作者：Hongjie Ruan、Ling-Guo Meng、Hailong Xu、Yuqing Liang、Lei Wang

  DOI：10.1039/c9ob02750e

  日期：——

  A coupling of bromoalkynes with secondary phosphine oxides was developed for the synthesis of alkynylphosphine oxides. This transformation was accomplished under additive-free conditions in acetic anhydride (Ac2O). The reaction could be carried out under mild conditions, and a wide range of secondary phosphine oxides were obtained in good yields.

  溴代炔烃与仲膦氧化物的偶联被开发用于炔基膦氧化物的合成。该转化是在无添加剂的乙酸酐（Ac2O）条件下完成的。该反应可以在温和的条件下进行，并且以高收率获得了多种仲氧化膦。
• One-Pot Transformation of Ph₂P(O)-Protected Ethynes: Deprotection Followed by Transition Metal-Catalyzed Coupling
  作者：Lifen Peng、Feng Xu、Yoshinori Suzuma、Akihiro Orita、Junzo Otera

  DOI：10.1021/jo402176w

  日期：2013.12.20

  Ph2P(O)-protected ethynes were successfully transformed to arylethynes in one-pot manner through t-BuOK-catalyzed deprotection followed by Sonogashira coupling with aryl halide. The arylethynes were obtained similarly by Ph2P(O)-deprotection, stannylation of the resulting terminal ethynes, and Migita-Kosugi-Stille coupling. Deprotection followed by intramolecular Eglinton coupling could be carried out in one-pot to provide cyclic butadiynes.