cis-4-ethyl-3-(trimethylsilyl)-2-oxetanone | 67354-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: cis-4-ethyl-3-(trimethylsilyl)-2-oxetanone
• 英文别名: (3S,4R)-4-Ethyl-3-(trimethylsilyl)oxetan-2-one；(3S,4R)-4-ethyl-3-trimethylsilyloxetan-2-one
• CAS: 67354-22-7
• 化学式: C₈H₁₆O₂Si
• 分子量: 172.299
• InChiKey: HSLKCCNEEPYDMB-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基硅烷基乙烯酮 、 丙醛 在 methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到cis-4-ethyl-3-(trimethylsilyl)-2-oxetanone
  参考文献：
  名称：

  Organoaluminum-promoted cycloaddition of trialkylsilylketene with aldehydes: A new, stereoselective approach to cis-2-oxetanones and 2(Z)-alkenoic acids

  摘要：

  The exceptionally bulky methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR) can be successfully utilized as a highly efficient Lewis acid for achieving high stereoselectivity in the cycloaddition of trialkylsilylketene with aldehydes. This method serves as a highly effective route to the synthesis of cis-2-oxetanones from saturated aldehydes, and the synthesis of 2(Z)-alkenoic acids from aromatic and alpha,beta-unsaturated aldehydes.

  DOI：

  10.1016/0040-4020(95)00142-u

文献信息

• Organoaluminum-promoted cycloaddition of trialkylsilylketene with aldehydes: A new, stereoselective approach to cis-2-oxetanones and 2(Z)-alkenoic acids
  作者：Arnel B Concepcion、Keiji Maruoka、Hisashi Yamamoto

  DOI：10.1016/0040-4020(95)00142-u

  日期：1995.4

  The exceptionally bulky methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR) can be successfully utilized as a highly efficient Lewis acid for achieving high stereoselectivity in the cycloaddition of trialkylsilylketene with aldehydes. This method serves as a highly effective route to the synthesis of cis-2-oxetanones from saturated aldehydes, and the synthesis of 2(Z)-alkenoic acids from aromatic and alpha,beta-unsaturated aldehydes.