(1'R)-3-methyl-3-(4'-methyl-3'-cyclohexenyl)-cyclobutanone | 153171-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'R)-3-methyl-3-(4'-methyl-3'-cyclohexenyl)-cyclobutanone
• 英文别名: Cyclobutanone, 3-methyl-3-(4-methyl-3-cyclohexen-1-yl)-, (R)-；3-methyl-3-[(1R)-4-methylcyclohex-3-en-1-yl]cyclobutan-1-one
• CAS: 153171-38-1
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: USVHZNSZEKCQBF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1'R)-3-methyl-3-(4'-methyl-3'-cyclohexenyl)-cyclobutanone 在 sodium hypochlorite 、 溶剂黄146 作用下， 反应 0.33h， 以92%的产率得到(1'R,3RS)-3-methyl-3-(4'-methyl-3'-cyclohexenyl)-γ-butyrolactone
  参考文献：
  名称：

  Regiospecific Baeyer-Villiger Oxidation of α,α-Dichlorocyclobutanones: A Norbisabolide γ-lactone Analogue¹

  摘要：

  Details and methodological comparisons are presented on the preparation of a norbisabolide gamma-lactone analogue (4) via dichloroketene cycloaddition to limonene followed by regioselective Baeyer-Villiger oxidation (CH3CO3H) of the alpha,alpha-dichlorocyclobutanones 3 and C-Cl reduction (Zn/HOAc). The sequence of reduction followed by oxidation (HOCl) applied to 3 produced 4 in much better yield.

  DOI：

  10.1080/00397919308012611
• 作为产物：
  描述：

  (1'R,3RS)-2,2-dichloro-3-methyl-3-(4'-methyl-3'-cyclohexenyl)cyclobutanone 在 溶剂黄146 、 锌 作用下， 反应 1.0h， 以100%的产率得到(1'R)-3-methyl-3-(4'-methyl-3'-cyclohexenyl)-cyclobutanone
  参考文献：
  名称：

  Regiospecific Baeyer-Villiger Oxidation of α,α-Dichlorocyclobutanones: A Norbisabolide γ-lactone Analogue¹

  摘要：

  Details and methodological comparisons are presented on the preparation of a norbisabolide gamma-lactone analogue (4) via dichloroketene cycloaddition to limonene followed by regioselective Baeyer-Villiger oxidation (CH3CO3H) of the alpha,alpha-dichlorocyclobutanones 3 and C-Cl reduction (Zn/HOAc). The sequence of reduction followed by oxidation (HOCl) applied to 3 produced 4 in much better yield.

  DOI：

  10.1080/00397919308012611

文献信息

• Free radical annulation of dichlorocyclobutanones with sequential ring expansion
  作者：Paul Dowd、Wei Zhang、Steven J. Geib

  DOI：10.1016/0040-4020(95)00093-n

  日期：1995.3

  reaction of dichloroketene with 1,5-dienes undergo intramolecular free radical annulation. Lewis acid-promoted ring-opening of the cyclized cyclobutanones then yields novel ring expansion products. Reaction of (R)-carvone provides an unusual example leading to the formation of a tricyclic dione. The carbonyl group of carvone enhances the radical cyclization and influences the ring-opening pathway.

  描述了一种新的合成序列，该序列在1，5-二烯的末端添加了烯酮的元素。由二氯乙烯酮与1，5-二烯反应产生的二氯环丁酮加合物经历分子内自由基环化。然后路易斯酸促进环化环丁酮的开环，产生新的扩环产物。（R）-香芹酮的反应提供了导致形成三环二酮的不寻常的例子。香芹酮的羰基增强自由基环化并影响开环途径。