4,5,6,7-Tetramethyl-2-indanon | 60998-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4,5,6,7-Tetramethyl-2-indanon
• 英文别名: 4,5,6,7-Tetramethylindan-2-on；4,5,6,7-tetramethylindane-2-one；4,5,6,7-tetramethyl-1,3-dihydro-2H-inden-2-one；4,5,6,7-tetramethyl-1,3-dihydroinden-2-one
• CAS: 60998-58-5
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: ZFSBHDGHTHAODO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二茂铁 、 4,5,6,7-Tetramethyl-2-indanon 、 叔丁基锂 在 HCl 作用下， 以 正戊烷 为溶剂， 以17%的产率得到2-ferrocenyl-4,5,6,7-tetramethylindene
  参考文献：
  名称：

  Charge Transfer through Isomeric Unsaturated Hydrocarbons. Redox Switchable Optical Properties and Electronic Structure of Substituted Indenes with a Pendant Ferrocenyl

  摘要：

  A family of (ferrocenyl)indenes, (2-ferrocenyl)indene, (2-ferrocenyl)tetramethylindene, (2-ferrocenyl)hexamethylindene, (3-ferrocenyl)indene, and (3-ferrocenyl)hexamethylindene, and the corresponding monooxidized cations have been prepared. The results of a structural and spectroelectrochemical study are discussed. The availability of pairs of isomers with known geometries and differently methylated indenes allowed the detailed investigation of how slight geometric and electronic modifications affect their physical properties. The molecular structures have been determined by X-ray diffraction and compared with the fully optimized structures calculated with state-of-the-art DFT methods. Calculated and crystallographic structures agree in establishing the dependence of the orientation of the indene moiety and the ferrocenyl cyclopentadienyl rings on the degree of methylation. The UV-vis spectra and in particular the appearance upon oxidation of a new near-IR absorption, whose energy and intensity increase with the degree of methylation and cyclopentadienyl-indene planarity, are rationalized in the framework of the Hush theory and at quantum chemistry level by DFT and TD-DFT calculations.

  DOI：

  10.1021/om700673m
• 作为产物：
  描述：

  一氧化碳 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 3.0h， 以64%的产率得到4,5,6,7-Tetramethyl-2-indanon
  参考文献：
  名称：

  Erker, Gerhard; Engel, Klaus; Krueger, Carl, Chemische Berichte, 1982, vol. 115, # 10, p. 3311 - 3323

  摘要：

  DOI：

文献信息

• Novel rhodium-catalyzed additions of carbon monoxide to reactive dienes and enones with formation of five-membered rings
  作者：R. F. Heldeweg、H. Hogeveen

  DOI：10.1021/ja00435a046

  日期：1976.9
• Charge Transfer through Isomeric Unsaturated Hydrocarbons. Redox Switchable Optical Properties and Electronic Structure of Substituted Indenes with a Pendant Ferrocenyl
  作者：Saverio Santi、Laura Orian、Alessandro Donoli、Christian Durante、Annalisa Bisello、Paolo Ganis、Alberto Ceccon、Laura Crociani、Franco Benetollo

  DOI：10.1021/om700673m

  日期：2007.11.1

  A family of (ferrocenyl)indenes, (2-ferrocenyl)indene, (2-ferrocenyl)tetramethylindene, (2-ferrocenyl)hexamethylindene, (3-ferrocenyl)indene, and (3-ferrocenyl)hexamethylindene, and the corresponding monooxidized cations have been prepared. The results of a structural and spectroelectrochemical study are discussed. The availability of pairs of isomers with known geometries and differently methylated indenes allowed the detailed investigation of how slight geometric and electronic modifications affect their physical properties. The molecular structures have been determined by X-ray diffraction and compared with the fully optimized structures calculated with state-of-the-art DFT methods. Calculated and crystallographic structures agree in establishing the dependence of the orientation of the indene moiety and the ferrocenyl cyclopentadienyl rings on the degree of methylation. The UV-vis spectra and in particular the appearance upon oxidation of a new near-IR absorption, whose energy and intensity increase with the degree of methylation and cyclopentadienyl-indene planarity, are rationalized in the framework of the Hush theory and at quantum chemistry level by DFT and TD-DFT calculations.
• Erker, Gerhard; Engel, Klaus; Krueger, Carl, Chemische Berichte, 1982, vol. 115, # 10, p. 3311 - 3323
  作者：Erker, Gerhard、Engel, Klaus、Krueger, Carl、Chiang, An-Pei

  DOI：——

  日期：——