6,13-bis(triisopropylsiloxy)-9,10-(diphenylmethylenedioxy)[7]helicenebisquinone | 215385-44-7

• 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: 6,13-bis(triisopropylsiloxy)-9,10-(diphenylmethylenedioxy)[7]helicenebisquinone
• 英文别名: 18,18-Diphenyl-11,25-bis[tri(propan-2-yl)silyloxy]-17,19-dioxaoctacyclo[19.12.0.02,15.03,12.04,9.016,20.024,33.027,32]tritriaconta-1(21),2(15),3,6,9,11,13,16(20),22,24,26,29,32-tridecaene-5,8,28,31-tetrone
• CAS: 215385-44-7
• 化学式: C₆₁H₆₂O₈Si₂
• 分子量: 979.329
• InChiKey: OOCRSLOLIVPGMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.95
• 重原子数：
  71
• 可旋转键数：
  12
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-碘十二烷 、 6,13-bis(triisopropylsiloxy)-9,10-(diphenylmethylenedioxy)[7]helicenebisquinone 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以88%的产率得到(M)-3,6-bis(dodecyloxy)-9,10-(diphenylmethylenedioxy)[7]helicenebisquinone
  参考文献：
  名称：

  Efficient Synthesis of Functionalized [7]Helicenes

  摘要：

  [7]Helicenebisquinones can be made easily and in quantity by reacting the silyl enol ethers of a 9,10-dialkoxy-, or better a 9,10-disiloxy-, 3,6-diacetylphenanthrene, with p-benzoquinone. If an ethyl, enol ether is used in place of the silyl enol ether, the transformation proceeds in much lower yield. The [7]helicenes are efficiently resolved into their enantiomers, and absolute configurations are assigned.

  DOI：

  10.1021/jo981380y
• 作为产物：
  描述：

  3,6-diacetyl-9,10-(diphenylmethylenedioxy)phenanthrene 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 65.0h， 生成 6,13-bis(triisopropylsiloxy)-9,10-(diphenylmethylenedioxy)[7]helicenebisquinone
  参考文献：
  名称：

  Efficient Synthesis of Functionalized [7]Helicenes

  摘要：

  [7]Helicenebisquinones can be made easily and in quantity by reacting the silyl enol ethers of a 9,10-dialkoxy-, or better a 9,10-disiloxy-, 3,6-diacetylphenanthrene, with p-benzoquinone. If an ethyl, enol ether is used in place of the silyl enol ether, the transformation proceeds in much lower yield. The [7]helicenes are efficiently resolved into their enantiomers, and absolute configurations are assigned.

  DOI：

  10.1021/jo981380y

文献信息

• Efficient Synthesis of Functionalized [7]Helicenes
  作者：Joseph M. Fox、Naomi R. Goldberg、Thomas J. Katz

  DOI：10.1021/jo981380y

  日期：1998.10.1

  [7]Helicenebisquinones can be made easily and in quantity by reacting the silyl enol ethers of a 9,10-dialkoxy-, or better a 9,10-disiloxy-, 3,6-diacetylphenanthrene, with p-benzoquinone. If an ethyl, enol ether is used in place of the silyl enol ether, the transformation proceeds in much lower yield. The [7]helicenes are efficiently resolved into their enantiomers, and absolute configurations are assigned.