5,5-Dimethyl-1'-[2-[2-(2-phenylethynyl)phenyl]ethynyl]spiro[1,3-dioxane-2,2'-acenaphthylene]-1'-ol | 246227-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,5-Dimethyl-1'-[2-[2-(2-phenylethynyl)phenyl]ethynyl]spiro[1,3-dioxane-2,2'-acenaphthylene]-1'-ol
• CAS: 246227-80-5
• 化学式: C₃₃H₂₆O₃
• 分子量: 470.568
• InChiKey: GGKOQYDUKRXVAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-Dimethyl-1'-[2-[2-(2-phenylethynyl)phenyl]ethynyl]spiro[1,3-dioxane-2,2'-acenaphthylene]-1'-ol 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到3'-Chloro-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]
  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'-Dimethylacenaphthene-1-spiro-2'-[1,3]dioxan-2-one 、 1-乙炔基-2-(2-苯基乙炔基)苯 在 正丁基锂 、 水 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 12.0h， 以77%的产率得到5,5-Dimethyl-1'-[2-[2-(2-phenylethynyl)phenyl]ethynyl]spiro[1,3-dioxane-2,2'-acenaphthylene]-1'-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.