diphenyl bromo(4-cyanophenyl)methylphosphonate | 1070910-50-7

• 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: diphenyl bromo(4-cyanophenyl)methylphosphonate
• CAS: 1070910-50-7
• 化学式: C₂₀H₁₅BrNO₃P
• 分子量: 428.222
• InChiKey: RONWKORQJPJAPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diphenyl bromo(4-cyanophenyl)methylphosphonate 、 2-formyl-5,10,15,20-tetraphenylporphyrin 在 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 2-(4'-cyanophenyl)ethynyl-5,10,15,20-tetraphenylporphyrin 、 2-(4'-benzamide)ethynyl-5,10,15,20-tetraphenylporphyrin
  参考文献：
  名称：

  An alternative synthesis of β-pyrrolic acetylene-substituted porphyrins

  摘要：

  A modified Horner-Emmons condensation reaction has been employed in the synthesis of acetylene-substituted porphyrins at the beta-pyrrolic position. This technique was shown to have many advantages over the typically employed Sonogashira coupling method, including negating the requirement for a brominated porphyrin starting material. The electronic spectra of 2-(4'-carboxyphenyl)ethynyl-5,10,15,20-tetraphenylporphyrinato zinc(II) showed a red shift compared to the double bond equivalent, 4-(trans-2'-(2 ''-(5 '', 10 '', 15 '',20 ''-tetraphenylporphyrinato zinc(II)yl))ethen-1'-yl)-1-benzoic acid. Comparison of the X-ray structures of 2-((4'-formyl)phenyl)ethynyl-5,10,15,20-tetraphenylporphyrinato zinc(II) and its analogue 4-(trans-2'(2 ''-(5 '',10 '',15 '',20 ''-tetraphenylporphyrinato copper(II)yl))ethen-1'-yl)-1-benzaldehyde showed all unexpected decrease in planarity in the analogue with the triple bond as opposed to that with the double bond. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.059
• 作为产物：
  描述：

  diphenyl hydroxy(4-cyanophenyl)methylphosphonate 在 四丁基溴化铵 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 diphenyl bromo(4-cyanophenyl)methylphosphonate
  参考文献：
  名称：

  An alternative synthesis of β-pyrrolic acetylene-substituted porphyrins

  摘要：

  A modified Horner-Emmons condensation reaction has been employed in the synthesis of acetylene-substituted porphyrins at the beta-pyrrolic position. This technique was shown to have many advantages over the typically employed Sonogashira coupling method, including negating the requirement for a brominated porphyrin starting material. The electronic spectra of 2-(4'-carboxyphenyl)ethynyl-5,10,15,20-tetraphenylporphyrinato zinc(II) showed a red shift compared to the double bond equivalent, 4-(trans-2'-(2 ''-(5 '', 10 '', 15 '',20 ''-tetraphenylporphyrinato zinc(II)yl))ethen-1'-yl)-1-benzoic acid. Comparison of the X-ray structures of 2-((4'-formyl)phenyl)ethynyl-5,10,15,20-tetraphenylporphyrinato zinc(II) and its analogue 4-(trans-2'(2 ''-(5 '',10 '',15 '',20 ''-tetraphenylporphyrinato copper(II)yl))ethen-1'-yl)-1-benzaldehyde showed all unexpected decrease in planarity in the analogue with the triple bond as opposed to that with the double bond. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.059