6'-methoxyspiro[cyclohexane-1,1'-(2',3'-dihydroindene)]-2,6-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6'-methoxyspiro[cyclohexane-1,1'-(2',3'-dihydroindene)]-2,6-dione
• 英文别名: 6'-methoxyspiro[cyclohexane-1,1'-indan]-2,6-dione；5-Methoxyspiro[1,2-dihydroindene-3,2'-cyclohexane]-1',3'-dione
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: DMEPRBXDHXVSRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯乙基溴 在 咪唑 、 盐酸 、 萘-1,4-二腈 、 叔丁基锂 作用下， 以 四氢呋喃 、 水 、 丙酮 、 乙腈 、 正戊烷 为溶剂， 反应 2.0h， 生成 6'-methoxyspiro[cyclohexane-1,1'-(2',3'-dihydroindene)]-2,6-dione
  参考文献：
  名称：

  New Intramolecular α-Arylation Strategy of Ketones by the Reaction of Silyl Enol Ethers to Photosensitized Electron Transfer Generated Arene Radical Cations:  Construction of Benzannulated and Benzospiroannulated Compounds

  摘要：

  Efficient intramolecular alpha-arylation of ketones is achieved by the reaction of silyl enol ethers to photosensitized electron transfer (PET) generated arene radical cations. The arene radical cations are generated by one-electron transfer from the excited state of the methoxy-substituted arenes to ground-state 1,4-dicyanonaphthalene (DCN). This arylation strategy has provided the unique opportunity of constructing five- (23), six- (18), seven- (25) and eight-membered (27) benzannulated as well as benzospiroannulated (34) compounds. The explanation for the formation of 27 has been advanced by considering the proximity between the arene radical cation and silyl enol ether due to the self-coiling in the aqueous environment.

  DOI：

  10.1021/jo9718612

文献信息

• Hypervalent Iodine(III)-Induced Intramolecular Cyclization of α-(Aryl)alkyl-β-dicarbonyl Compounds:  A Convenient Synthesis of Benzannulated and Spirobenzannulated Compounds
  作者：Mitsuhiro Arisawa、Namakkal G. Ramesh、Makiko Nakajima、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1021/jo000953f

  日期：2001.1.1

  A novel hypervalent iodine(III)-induced direct intramolecular cyclization of alpha-(aryl)alkyl-beta -dicarbonyl compounds has been described. Both meta-and para-substituted phenol ether derivatives containing acyclic or cyclic 1,3-dicarbonyl moieties at the side chain undergo this reaction in a facile manner. The reactions afford benzannulated and spirobenzannulated compounds that are of biological importance. The reaction is found to be general, mild,: and high yielding. The mechanism: of the reaction has been shown to involve a cation radical intermediate.
• New Intramolecular α-Arylation Strategy of Ketones by the Reaction of Silyl Enol Ethers to Photosensitized Electron Transfer Generated Arene Radical Cations:  Construction of Benzannulated and Benzospiroannulated Compounds
  作者：Ganesh Pandey、M. Karthikeyan、A. Murugan

  DOI：10.1021/jo9718612

  日期：1998.5.1

  Efficient intramolecular alpha-arylation of ketones is achieved by the reaction of silyl enol ethers to photosensitized electron transfer (PET) generated arene radical cations. The arene radical cations are generated by one-electron transfer from the excited state of the methoxy-substituted arenes to ground-state 1,4-dicyanonaphthalene (DCN). This arylation strategy has provided the unique opportunity of constructing five- (23), six- (18), seven- (25) and eight-membered (27) benzannulated as well as benzospiroannulated (34) compounds. The explanation for the formation of 27 has been advanced by considering the proximity between the arene radical cation and silyl enol ether due to the self-coiling in the aqueous environment.