11-Phenyl-22-[2-[2-(2-phenylethynyl)phenyl]ethynyl]hexacyclo[17.2.1.02,10.04,9.012,21.015,20]docosa-1,4,6,8,10,12(21),13,15(20),16,18-decaen-22-ol | 246227-87-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 11-Phenyl-22-[2-[2-(2-phenylethynyl)phenyl]ethynyl]hexacyclo[17.2.1.02,10.04,9.012,21.015,20]docosa-1,4,6,8,10,12(21),13,15(20),16,18-decaen-22-ol
• CAS: 246227-87-2
• 化学式: C₄₄H₂₆O
• 分子量: 570.69
• InChiKey: ALJVMMXCKZGUPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-Phenyl-22-[2-[2-(2-phenylethynyl)phenyl]ethynyl]hexacyclo[17.2.1.02,10.04,9.012,21.015,20]docosa-1,4,6,8,10,12(21),13,15(20),16,18-decaen-22-ol 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 5-Chloro-13,21-diphenylnonacyclo[15.15.0.02,14.03,31.04,12.06,11.020,32.022,30.023,28]dotriaconta-1(17),2(14),3,6,8,10,12,15,18,20(32),21,23,25,27,30-pentadecaene
  参考文献：
  名称：

  Synthesis of a C₄₄H₂₆ Hydrocarbon Having a Carbon Framework Represented on the Surface of C₆₀ via Benzoenyne-Allenes

  摘要：

  The C44H26 hydrocarbon 20 was synthesized in 13% overall yield in eight steps from acenaphthenequinone (6) and 2 equiv of 1-(2-ethynylphenyl)-2-phenylethyne, Condensation of the monoketal 7 with the lithium acetylide 8 afforded the benzoenediynyl propargylic alcohol 9. On exposure to thionyl chloride, 9 underwent a cascade of reactions with the formation of the chloro-substituted benzoenyne-allene II in situ followed by a C2-C6 cyclization to produce the biradical 12, leading to the formal Diels-Alder adduct 13 and subsequently, after tautomerization, the chloride 14. Reduction with sodium borohydride then gave 15. Deprotection of the ketal group produced 16 to allow a repeat of condensation with the acetylide 17 followed by the cascade transformation to afford the chloride 19. Subsequent reduction then furnished the C44H26 hydrocarbon 20 having a carbon framework represented on the surface of C-60.

  DOI：

  10.1021/jo9911903
• 作为产物：
  描述：

  5,5-Dimethyl-11'-phenylspiro[1,3-dioxane-2,22'-hexacyclo[17.2.1.02,10.04,9.012,21.015,20]docosa-1,4,6,8,10,12(21),13,15(20),16,18-decaene] 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 23.0h， 生成 11-Phenyl-22-[2-[2-(2-phenylethynyl)phenyl]ethynyl]hexacyclo[17.2.1.02,10.04,9.012,21.015,20]docosa-1,4,6,8,10,12(21),13,15(20),16,18-decaen-22-ol
  参考文献：
  名称：

  Synthesis of a C₄₄H₂₆ Hydrocarbon Having a Carbon Framework Represented on the Surface of C₆₀ via Benzoenyne-Allenes

  摘要：

  The C44H26 hydrocarbon 20 was synthesized in 13% overall yield in eight steps from acenaphthenequinone (6) and 2 equiv of 1-(2-ethynylphenyl)-2-phenylethyne, Condensation of the monoketal 7 with the lithium acetylide 8 afforded the benzoenediynyl propargylic alcohol 9. On exposure to thionyl chloride, 9 underwent a cascade of reactions with the formation of the chloro-substituted benzoenyne-allene II in situ followed by a C2-C6 cyclization to produce the biradical 12, leading to the formal Diels-Alder adduct 13 and subsequently, after tautomerization, the chloride 14. Reduction with sodium borohydride then gave 15. Deprotection of the ketal group produced 16 to allow a repeat of condensation with the acetylide 17 followed by the cascade transformation to afford the chloride 19. Subsequent reduction then furnished the C44H26 hydrocarbon 20 having a carbon framework represented on the surface of C-60.

  DOI：

  10.1021/jo9911903

文献信息

• Synthesis of a C₄₄H₂₆ Hydrocarbon Having a Carbon Framework Represented on the Surface of C₆₀ via Benzoenyne-Allenes
  作者：Hai-Ren Zhang、Kung K. Wang

  DOI：10.1021/jo9911903

  日期：1999.10.1

  The C44H26 hydrocarbon 20 was synthesized in 13% overall yield in eight steps from acenaphthenequinone (6) and 2 equiv of 1-(2-ethynylphenyl)-2-phenylethyne, Condensation of the monoketal 7 with the lithium acetylide 8 afforded the benzoenediynyl propargylic alcohol 9. On exposure to thionyl chloride, 9 underwent a cascade of reactions with the formation of the chloro-substituted benzoenyne-allene II in situ followed by a C2-C6 cyclization to produce the biradical 12, leading to the formal Diels-Alder adduct 13 and subsequently, after tautomerization, the chloride 14. Reduction with sodium borohydride then gave 15. Deprotection of the ketal group produced 16 to allow a repeat of condensation with the acetylide 17 followed by the cascade transformation to afford the chloride 19. Subsequent reduction then furnished the C44H26 hydrocarbon 20 having a carbon framework represented on the surface of C-60.