2,2-dimethylspiro[4,5]decane-1,4-dione | 198697-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethylspiro[4,5]decane-1,4-dione
• 英文别名: 3,3-Dimethylspiro[4.5]decane-1,4-dione
• CAS: 198697-21-1
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: KTMKAALPDQZXIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethylspiro[4,5]decane-1,4-dione 在 甲酸 、 hydroxylamine-O-sulfonic acid 作用下， 反应 3.0h， 以79%的产率得到5-aza-2,2-dimethylspiro[5.5]undecane-1,4-dione
  参考文献：
  名称：

  Elliott, Christine E.; Miller, David O.; Burnell, D. Jean, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 217 - 226

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxy-2-(1-hydroxycyclohexyl)-4,4-dimethylcyclobutanone 在 三氟乙酸 作用下， 生成 2,2-dimethylspiro[4,5]decane-1,4-dione
  参考文献：
  名称：

  Geminal Acylation of Ketones Mediated by Boron Trichloride. An Improved Method for the Synthesis of 4,4-Dimethyl-1,3-cyclopentanediones

  摘要：

  DOI：

  10.1021/jo9806308

文献信息

• Geminal Acylation with Methyl-Substituted Analogues of 1,2-Bis[(trimethylsilyl)oxy]cyclobutene
  作者：Sheldon N. Crane、Tracy J. Jenkins、D. Jean Burnell

  DOI：10.1021/jo971055v

  日期：1997.12.1

  BF3 . Et2O-catalyzed geminal acylation of ketones and acetals with 3-methyl-1,2-bis[(trimethylsilyl)oxy)]cyclobutene (3) provided methylcyclopentanediones in yields that ranged from 40 to 94%. The best substrates were unhindered cyclohexanones. With acetals, stereochemical preferences in the initial Mukaiyama-like aldol step giving cyclobutanones translated into the stereochemistry of the ultimate cyclopentanedione products. With ketones, equilibration of the initial cyclobutanone compounds resulted in cyclopentanedione products with a different stereochemical preference. The gem-dimethylcyclobutene reagent 4 reacted with ketones to give gem-dimethylcyclopentanediones in modest yield. The process was much more stereochemically efficient than the reaction with 3. Rearrangement from the initial cyclobutanone compound was partially diverted toward air-sensitive 3-furanone compounds and ring-opened 1,2-diones. Only furanones (e.g., 52 and 53) were isolated from reactions with the tetramethylcyclobutene 51.
• Elliott, Christine E.; Miller, David O.; Burnell, D. Jean, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 217 - 226
  作者：Elliott, Christine E.、Miller, David O.、Burnell, D. Jean

  DOI：——

  日期：——
• Geminal Acylation of Ketones Mediated by Boron Trichloride. An Improved Method for the Synthesis of 4,4-Dimethyl-1,3-cyclopentanediones
  作者：Sheldon N. Crane、D. Jean Burnell

  DOI：10.1021/jo9806308

  日期：1998.8.1