4,5-dihydro-5,5-dimethyl-2-(2-methylcyclohexylidene)-3(2H)-furanone | 198697-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4,5-dihydro-5,5-dimethyl-2-(2-methylcyclohexylidene)-3(2H)-furanone
• 英文别名: 5,5-dimethyl-2-(2-methylcyclohexylidene)oxolan-3-one
• CAS: 198697-27-7
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: PNDWKRICZXSHOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-5,5-dimethyl-2-(2-methylcyclohexylidene)-3(2H)-furanone 在 air 作用下， 生成 (1'R/S,2R/S,2'S/R)-4,5-dihydro-2-hydroxy-2-(1-hydroxy-2-methylcyclohexyl)-5,5-dimethyl-3(2H)-furanone 、 (1'R/S,2R/S,2'R/S)-4,5-dihydro-2-hydroxy-2-(1-hydroxy-2-methylcyclohexyl)-5,5-dimethyl-3(2H)-furanone
  参考文献：
  名称：

  Geminal Acylation with Methyl-Substituted Analogues of 1,2-Bis[(trimethylsilyl)oxy]cyclobutene

  摘要：

  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.

  DOI：

  10.1021/jo971055v
• 作为产物：
  描述：

  (1'R*,2'R*)-2-hydroxy-4,4-dimethyl-2-(1-hydroxy-2-methylcyclohexyl)cyclobutanone 在 三氟乙酸 作用下， 反应 7.0h， 生成 4,5-dihydro-5,5-dimethyl-2-(2-methylcyclohexylidene)-3(2H)-furanone 、 2,2,6-trimethylspiro[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