3,5-bis(diphenylphosphinoylmethyl)iodobenzene | 263353-14-6

• 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: 3,5-bis(diphenylphosphinoylmethyl)iodobenzene
• 英文别名: 3,5-Bis(diphenylphosphinoyl-methyl)iodobenzene；1,3-bis(diphenylphosphorylmethyl)-5-iodobenzene
• CAS: 263353-14-6
• 化学式: C₃₂H₂₇IO₂P₂
• 分子量: 632.417
• InChiKey: BHYLHMYQEDMVOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-bis(diphenylphosphinoylmethyl)iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 3,5-bis[(diphenylphosphinoxide)methyl]phenylacetylene
  参考文献：
  名称：

  Synthesis and Catalytic Properties of Di- and Trinuclear Palladium Complexes with PCP-Pincer Ligands

  摘要：

  Linear and branched conjugated pincer ligands having Ph(2)p groups were synthesized: 3,3'5,5- tetrakis(diphenylphosphinomethyl)diphenylacetylene, 3,3',5,5'-tetrakis(diphenylphosphinomethyl)diphenyldiacetylene, 1,3,5-tris[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene, and hexakis[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene. Palladation of these ligands by heating with Pd(BF4)(2)(MeCN)(4) in boiling acetonitrile gave the corresponding di- and trinuclear ionic pincer palladium complexes. No individual complex was obtained from hexakis [3,5 -bis(diphenylphosphinomethyl)phenylethynyl] benzene. The ionic complexes were converted into the corresponding chloride complexes by treatment with sodium chloride in a mixture of water with methylene chloride. The structure of the ionic palladium complex with 3,3%5,5 -tetrakis(diphenylphosphinomethyl)diphenylacetylene was established by X-ray analysis. The obtained palladium complexes exhibited a considerable catalytic activity in the Heck reaction of iodobenzene with ethyl acrylate and in the Michael addition of ethyl cyanoacetate with methyl vinyl ketone. The catalytic activity per palladium atom decreases as the number of palladium atoms in the complex increases.

  DOI：

  10.1023/b:rujo.0000010214.72250.5a
• 作为产物：
  描述：

  二苯基乙氧基膦 、 1,3-bis(bromomethyl)-5-iodobenzene 以 间二甲苯 为溶剂， 反应 1.0h， 以98%的产率得到3,5-bis(diphenylphosphinoylmethyl)iodobenzene
  参考文献：
  名称：

  Synthesis and Catalytic Properties of Di- and Trinuclear Palladium Complexes with PCP-Pincer Ligands

  摘要：

  Linear and branched conjugated pincer ligands having Ph(2)p groups were synthesized: 3,3'5,5- tetrakis(diphenylphosphinomethyl)diphenylacetylene, 3,3',5,5'-tetrakis(diphenylphosphinomethyl)diphenyldiacetylene, 1,3,5-tris[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene, and hexakis[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene. Palladation of these ligands by heating with Pd(BF4)(2)(MeCN)(4) in boiling acetonitrile gave the corresponding di- and trinuclear ionic pincer palladium complexes. No individual complex was obtained from hexakis [3,5 -bis(diphenylphosphinomethyl)phenylethynyl] benzene. The ionic complexes were converted into the corresponding chloride complexes by treatment with sodium chloride in a mixture of water with methylene chloride. The structure of the ionic palladium complex with 3,3%5,5 -tetrakis(diphenylphosphinomethyl)diphenylacetylene was established by X-ray analysis. The obtained palladium complexes exhibited a considerable catalytic activity in the Heck reaction of iodobenzene with ethyl acrylate and in the Michael addition of ethyl cyanoacetate with methyl vinyl ketone. The catalytic activity per palladium atom decreases as the number of palladium atoms in the complex increases.

  DOI：

  10.1023/b:rujo.0000010214.72250.5a

文献信息

• Acetylene-bridged P,C,P′-ligands and corresponding cyclopalladated compounds
  作者：Irina P Beletskaya、Alexey V Chuchurjukin、Harm P Dijkstra、Gerard P.M van Klink、Gerard van Koten

  DOI：10.1016/s0040-4039(99)02181-4

  日期：2000.2

  Bis-'pincer'-cyclopalladates 1 and 2 containing an ethynediyl- or a butadiynediyl-bridge have been synthesized, characterized and used as precatalysts in the Heck reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and Catalytic Properties of Di- and Trinuclear Palladium Complexes with PCP-Pincer Ligands
  作者：I. P. Beletskaya、A. V. Chuchuryukin、G. van Koten、H. P. Dijkstra、G. P. M. van Klink、A. N. Kashin、S. E. Nefedov、I. L. Eremenko

  DOI：10.1023/b:rujo.0000010214.72250.5a

  日期：2003.9

  Linear and branched conjugated pincer ligands having Ph(2)p groups were synthesized: 3,3'5,5- tetrakis(diphenylphosphinomethyl)diphenylacetylene, 3,3',5,5'-tetrakis(diphenylphosphinomethyl)diphenyldiacetylene, 1,3,5-tris[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene, and hexakis[3,5-bis(diphenylphosphinomethyl)phenylethynyl]benzene. Palladation of these ligands by heating with Pd(BF4)(2)(MeCN)(4) in boiling acetonitrile gave the corresponding di- and trinuclear ionic pincer palladium complexes. No individual complex was obtained from hexakis [3,5 -bis(diphenylphosphinomethyl)phenylethynyl] benzene. The ionic complexes were converted into the corresponding chloride complexes by treatment with sodium chloride in a mixture of water with methylene chloride. The structure of the ionic palladium complex with 3,3%5,5 -tetrakis(diphenylphosphinomethyl)diphenylacetylene was established by X-ray analysis. The obtained palladium complexes exhibited a considerable catalytic activity in the Heck reaction of iodobenzene with ethyl acrylate and in the Michael addition of ethyl cyanoacetate with methyl vinyl ketone. The catalytic activity per palladium atom decreases as the number of palladium atoms in the complex increases.