5,6,9,10-tetrahydropentahelicene-5,10-diyl diacetate | 1250981-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5,6,9,10-tetrahydropentahelicene-5,10-diyl diacetate
• 英文别名: (16-Acetyloxy-9-pentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(14),2(11),3,5,7,12,17,19,21-nonaenyl) acetate
• CAS: 1250981-24-8
• 化学式: C₂₆H₂₂O₄
• 分子量: 398.458
• InChiKey: RFFGUFFLUGZIHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6,9,10-tetrahydropentahelicene-5,10-diyl diacetate 在 silica gel 作用下， 反应 0.5h， 以93%的产率得到(5)螺烯
  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
• 作为产物：
  描述：

  ethyne-1,2-diylbis(benzene-2,1-diylbut-1-yne-4,4-diyl) diacetate 在 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 三苯基膦 作用下， 以 癸烷 为溶剂， 反应 2.0h， 以82%的产率得到5,6,9,10-tetrahydropentahelicene-5,10-diyl diacetate
  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