[pentahelicene-3,12-diylbis(benzene-4,1-diylethyne-2,1-diyl)]-bis[tris(1-methylethyl)silane] | 1250981-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [pentahelicene-3,12-diylbis(benzene-4,1-diylethyne-2,1-diyl)]-bis[tris(1-methylethyl)silane]
• 英文别名: Tri(propan-2-yl)-[2-[4-[19-[4-[2-tri(propan-2-yl)silylethynyl]phenyl]-6-pentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(14),2(11),3(8),4,6,9,12,15,17(22),18,20-undecaenyl]phenyl]ethynyl]silane
• CAS: 1250981-54-4
• 化学式: C₅₆H₆₂Si₂
• 分子量: 791.279
• InChiKey: BSDAJJQGMXZTIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.77
• 重原子数：
  58
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3,12-dichloropentahelicene 、 (4-((triisopropylsilyl)ethynyl)phenyl)boronic acid 在 palladium diacetate 、 caesium carbonate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以50%的产率得到[pentahelicene-3,12-diylbis(benzene-4,1-diylethyne-2,1-diyl)]-bis[tris(1-methylethyl)silane]
  参考文献：
  名称：

  A Versatile Synthesis of Functionalized Pentahelicenes

  摘要：

  A general synthetic methodology for the preparation of functionalized (hetero)helicenes has been developed It employs the sequence or a double propargyl ganometallics (Li, Mg, Ga/In) addition to it tolan-2.2'-dialdehyde-type intermediate. a cobalt-catalyzed/cobalt-media led [2 + 2 + 2] cycloisomerization of a triyne intermediate,and a double silica gel-assisted acetic acid elimination to receive pentahelicene, 1,14-diazapentahelicene. and 3,12-dichloro-, 3 12-dichloro-7trimethylsilyl- and 3,12-di-tert-butylpentahelicene 3,12-Dichloropentahelicene undergoes a Suzuki-Miyam a coupling with aryl boronic acids (or ester) under palladium catalysis to afford 3-12-diarylpentahelicenes

  DOI：

  10.1021/jo1013977

文献信息

• A Versatile Synthesis of Functionalized Pentahelicenes
  作者：Olivier Songis、Jiří Míšek、Markus B. Schmid、Adrian Kollárovič、Irena G. Stará、David Šaman、Ivana Císařová、Ivo Starý

  DOI：10.1021/jo1013977

  日期：2010.10.15

  A general synthetic methodology for the preparation of functionalized (hetero)helicenes has been developed It employs the sequence or a double propargyl ganometallics (Li, Mg, Ga/In) addition to it tolan-2.2'-dialdehyde-type intermediate. a cobalt-catalyzed/cobalt-media led [2 + 2 + 2] cycloisomerization of a triyne intermediate,and a double silica gel-assisted acetic acid elimination to receive pentahelicene, 1,14-diazapentahelicene. and 3,12-dichloro-, 3 12-dichloro-7trimethylsilyl- and 3,12-di-tert-butylpentahelicene 3,12-Dichloropentahelicene undergoes a Suzuki-Miyam a coupling with aryl boronic acids (or ester) under palladium catalysis to afford 3-12-diarylpentahelicenes