1-乙酰基-2,2-二甲基环丁烷 | 64507-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-乙酰基-2,2-二甲基环丁烷
• 英文名称: 1-acetyl-2,2-dimethylcyclobutane
• 英文别名: 1-(2,2-Dimethylcyclobutyl)ethanone
• CAS: 64507-84-2
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: ZSNURTPEYMQGJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  1-乙酰基-2,2-二甲基环丁烷 在 sodium hypobromide 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 3.0h， 生成 Methyl-(2,2-Dimethylcyclobutan)-carboxylat
  参考文献：
  名称：

  Selenium-directed stereoselective [2 + 2] cycloaddition reactions promoted by Lewis acids: a novel zwitterionic intermediate

  摘要：

  The reaction of (trimethylsilyl)vinyl selenide 1 and (trimethylsilyl)allenyl selenide 2 with vinyl ketones 3a-c in the presence of a Lewis acid gave cyclobutane derivatives stereoselectively. The reaction of 1 and 3a-c with SnCl4 was quenched either with Et3N to give cyclobutanes 4a-c or with H2O to give acylsilanes 11a-c. The formation of both products is explained in terms of a zwitterionic intermediate. The cis relationship between the phenylseleno group and the carbonyl group of 4a-c is rationalized by consideration of a combination of secondary-orbital interactions and steric effects in the early stage of intermediate formation.

  DOI：

  10.1021/jo00047a013
• 作为产物：
  描述：

  c-1-acetyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane 在 copper(l) iodide 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 1-乙酰基-2,2-二甲基环丁烷
  参考文献：
  名称：

  Selenium-directed stereoselective [2 + 2] cycloaddition reactions promoted by Lewis acids: a novel zwitterionic intermediate

  摘要：

  The reaction of (trimethylsilyl)vinyl selenide 1 and (trimethylsilyl)allenyl selenide 2 with vinyl ketones 3a-c in the presence of a Lewis acid gave cyclobutane derivatives stereoselectively. The reaction of 1 and 3a-c with SnCl4 was quenched either with Et3N to give cyclobutanes 4a-c or with H2O to give acylsilanes 11a-c. The formation of both products is explained in terms of a zwitterionic intermediate. The cis relationship between the phenylseleno group and the carbonyl group of 4a-c is rationalized by consideration of a combination of secondary-orbital interactions and steric effects in the early stage of intermediate formation.

  DOI：

  10.1021/jo00047a013

文献信息

• Chemistry of carbanions. 31. Cyclization of the metal enolates from .omega.-bromo ketones
  作者：Herbert O. House、William V. Phillips、Trevor S. B. Sayer、Cheuk-Chung Yau

  DOI：10.1021/jo00398a041

  日期：1978.2
• Selenium-directed stereoselective [2 + 2] cycloaddition reactions promoted by Lewis acids: a novel zwitterionic intermediate
  作者：Shoko Yamazaki、Hiroyuki Fujitsuka、Shinichi Yamabe、Hatsue Tamura

  DOI：10.1021/jo00047a013

  日期：1992.10

  The reaction of (trimethylsilyl)vinyl selenide 1 and (trimethylsilyl)allenyl selenide 2 with vinyl ketones 3a-c in the presence of a Lewis acid gave cyclobutane derivatives stereoselectively. The reaction of 1 and 3a-c with SnCl4 was quenched either with Et3N to give cyclobutanes 4a-c or with H2O to give acylsilanes 11a-c. The formation of both products is explained in terms of a zwitterionic intermediate. The cis relationship between the phenylseleno group and the carbonyl group of 4a-c is rationalized by consideration of a combination of secondary-orbital interactions and steric effects in the early stage of intermediate formation.