c-1-benzoyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane | 143370-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: c-1-benzoyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane
• 英文别名: phenyl-[(1R,2R)-2-phenylselanyl-2-trimethylsilylcyclobutyl]methanone
• CAS: 143370-47-2
• 化学式: C₂₀H₂₄OSeSi
• 分子量: 387.455
• InChiKey: SNQNYOYTMQNFNH-QUCCMNQESA-N

物化性质

• 沸点：
  446.8±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  c-1-benzoyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane 在 水 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以39%的产率得到1-phenyl-5-(trimethylsilyl)-1,5-pentanedione
  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：

  1-(Phenylseleno)-1-(trimethylsilyl)ethene 、 1-苯基-2-丙烯基-1-酮 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到c-1-benzoyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane
  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

• 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.