diphenyl<2,2-di(4-tert-butylphenyl)-1-iodoethenyl>phosphine oxide | 221458-69-1

• 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<2,2-di(4-tert-butylphenyl)-1-iodoethenyl>phosphine oxide
• 英文别名: 1-tert-butyl-4-[1-(4-tert-butylphenyl)-2-diphenylphosphoryl-2-iodoethenyl]benzene
• CAS: 221458-69-1
• 化学式: C₃₄H₃₆IOP
• 分子量: 618.538
• InChiKey: ZWDLEGCXXQIEQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.45
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  diphenyl<2,2-di(4-tert-butylphenyl)-1-iodoethenyl>phosphine oxide 在 1,4-环己二烯 、 叔丁基锂 作用下， 反应 1.5h， 生成 3,17-Bis[bis(4-tert-butylphenyl)methyl]octacyclo[16.10.1.14,11.02,16.05,10.019,24.025,29.015,30]triaconta-1(28),2(16),3,5,7,9,11(30),12,14,17,19,21,23,25(29),26-pentadecaene
  参考文献：
  名称：

  Thermolysis of Benzoenyne−Allenes To Form Biradicals and Subsequent Intramolecular Trapping with a Tetraarylallene To Generate Two Triarylmethyl Radical Centers

  摘要：

  Thermolysis of the benzoenyne-allene 20 in 1,4-cyclohexadiene (1,4-CHD) at 75 degrees C produced the cycloaromatized adduct 23 in 22% yield. The reaction presumably proceeds through a cascade sequence involving an initial Myers cyclization reaction to form the biradical 21. The subsequent trapping of the aryl radical center in 21 with the tetraarylallenic moiety intramolecularly affords 22, having two stabilized triarylmethyl radical centers. Hydrogen-atom abstraction from 1,4-CHD by 22, manifesting its radical character, then produces 23. Similarly, thermolysis of benzoenyne-allenes 25 in 1,4-CHD furnished fluoranthenes 27 in essentially quantitative yields. The presence of the fused five-membered ring in 20 and 25 is necessary to direct the initial biradical-forming step toward the Myers cyclization reaction. Without the five-membered ring as in the cases of 31, the C2-C6 cyclization reaction became the preferred pathway, leading to benzofluorenes 34.

  DOI：

  10.1021/jo982326k
• 作为产物：
  描述：

  4-叔丁基苯基溴化镁 、 ((4-(tert-butyl)phenyl)ethynyl)diphenylphosphine oxide 在 碘 、 copper(I) bromide 作用下， 生成 diphenyl<2,2-di(4-tert-butylphenyl)-1-iodoethenyl>phosphine oxide
  参考文献：
  名称：

  Thermolysis of Benzoenyne−Allenes To Form Biradicals and Subsequent Intramolecular Trapping with a Tetraarylallene To Generate Two Triarylmethyl Radical Centers

  摘要：

  Thermolysis of the benzoenyne-allene 20 in 1,4-cyclohexadiene (1,4-CHD) at 75 degrees C produced the cycloaromatized adduct 23 in 22% yield. The reaction presumably proceeds through a cascade sequence involving an initial Myers cyclization reaction to form the biradical 21. The subsequent trapping of the aryl radical center in 21 with the tetraarylallenic moiety intramolecularly affords 22, having two stabilized triarylmethyl radical centers. Hydrogen-atom abstraction from 1,4-CHD by 22, manifesting its radical character, then produces 23. Similarly, thermolysis of benzoenyne-allenes 25 in 1,4-CHD furnished fluoranthenes 27 in essentially quantitative yields. The presence of the fused five-membered ring in 20 and 25 is necessary to direct the initial biradical-forming step toward the Myers cyclization reaction. Without the five-membered ring as in the cases of 31, the C2-C6 cyclization reaction became the preferred pathway, leading to benzofluorenes 34.

  DOI：

  10.1021/jo982326k