2,2'-dibromo-5,5'-bis(4-biphenylyl)-4,4'-di-tert-butylbiphenyl | 351002-32-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,2'-dibromo-5,5'-bis(4-biphenylyl)-4,4'-di-tert-butylbiphenyl
• 英文别名: 1-Bromo-2-[2-bromo-4-tert-butyl-5-(4-phenylphenyl)phenyl]-5-tert-butyl-4-(4-phenylphenyl)benzene
• CAS: 351002-32-9
• 化学式: C₄₄H₄₀Br₂
• 分子量: 728.61
• InChiKey: NYXBPPXYOLDXIX-UHFFFAOYSA-N

物化性质

• 沸点：
  734.9±60.0 °C(predicted)
• 密度：
  1.252±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,2'-dibromo-5,5'-bis(4-biphenylyl)-4,4'-di-tert-butylbiphenyl 在 叔丁基锂 、 copper(ll) bromide 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 2.0h， 以40%的产率得到2,7,10,16-tetra-tert-butyl-3,6,11,15-tetrakis(4-biphenylyl)tetra-o-phenylene
  参考文献：
  名称：

  A Greek cross dodecaphenylene: sparteine-mediated asymmetric synthesis of chiral D2-symmetric π-conjugated tetra-o-phenylenes

  摘要：

  The asymmetric synthesis of a chiral, nonracemic pi -conjugated system with D-2 point group of symmetry, dodecaphenylene 4 is described. In the key step, (-)-sparteine- and Cu(II)-mediated oxidation of 2,2'-dilithio-1,1'-biaryls in ether gives the corresponding dimers, tetra-o-phenylenes, in 80% isolated yields and 50-60% ee's. X-Ray crystallography confirms the structure of rac-4 and its molecular shape of a Greek cross. The torsional angles between the benzene rings in the tetra-o-phenylene core of rac-4 are in the 56.5-71.0 degrees range. However, CD and UV spectra of 4 in CH2Cl2 are consistent with significant conjugation between the four terphenyl moieties. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00241-1
• 作为产物：
  描述：

  4-碘联苯 、 2,2',5,5'-tetrabromo-4,4'-di-tert-butylbiphenyl 在 叔丁基锂 、 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 2.0h， 以68%的产率得到2,2'-dibromo-5,5'-bis(4-biphenylyl)-4,4'-di-tert-butylbiphenyl
  参考文献：
  名称：

  A Greek cross dodecaphenylene: sparteine-mediated asymmetric synthesis of chiral D2-symmetric π-conjugated tetra-o-phenylenes

  摘要：

  The asymmetric synthesis of a chiral, nonracemic pi -conjugated system with D-2 point group of symmetry, dodecaphenylene 4 is described. In the key step, (-)-sparteine- and Cu(II)-mediated oxidation of 2,2'-dilithio-1,1'-biaryls in ether gives the corresponding dimers, tetra-o-phenylenes, in 80% isolated yields and 50-60% ee's. X-Ray crystallography confirms the structure of rac-4 and its molecular shape of a Greek cross. The torsional angles between the benzene rings in the tetra-o-phenylene core of rac-4 are in the 56.5-71.0 degrees range. However, CD and UV spectra of 4 in CH2Cl2 are consistent with significant conjugation between the four terphenyl moieties. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00241-1

文献信息

• A Greek cross dodecaphenylene: sparteine-mediated asymmetric synthesis of chiral D2-symmetric π-conjugated tetra-o-phenylenes
  作者：Andrzej Rajca、Hua Wang、Pavel Bolshov、Suchada Rajca

  DOI：10.1016/s0040-4020(01)00241-1

  日期：2001.4

  The asymmetric synthesis of a chiral, nonracemic pi -conjugated system with D-2 point group of symmetry, dodecaphenylene 4 is described. In the key step, (-)-sparteine- and Cu(II)-mediated oxidation of 2,2'-dilithio-1,1'-biaryls in ether gives the corresponding dimers, tetra-o-phenylenes, in 80% isolated yields and 50-60% ee's. X-Ray crystallography confirms the structure of rac-4 and its molecular shape of a Greek cross. The torsional angles between the benzene rings in the tetra-o-phenylene core of rac-4 are in the 56.5-71.0 degrees range. However, CD and UV spectra of 4 in CH2Cl2 are consistent with significant conjugation between the four terphenyl moieties. (C) 2001 Elsevier Science Ltd. All rights reserved.