2-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]cyclopent-3-en-1-ol | 606495-99-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]cyclopent-3-en-1-ol
• CAS: 606495-99-2
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: KNMQKEDIDHQVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  新戊酸乙烯酯 、 2-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]cyclopent-3-en-1-ol 在 Lipase PS 作用下， 以 异丙醚 为溶剂， 反应 48.0h， 以40%的产率得到[(1R,2S)-2-[2-[tert-butyl(dimethyl)silyl]oxyethyl]cyclopent-3-en-1-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Kinetic Resolution of Racemic 2-Substituted 3-Cyclopenten-1-ols by Lipase-Catalyzed Transesterifications:  A Rational Strategy To Improve Enantioselectivity

  摘要：

  The effect of the acyl group of acylating agents on the enantioselectivity in the Pseudomonas cepacia lipase-catalyzed acylations of racemic alcohols has been studied. 2-[(N,N-Dimethylcarbamoyl)methyl]-3-cyclopenten-1-ol (1) and 2-[2-(tert-butyldimethylsilyloxy)ethyl]-3-cyclopenten-1-ol (4) were resolved with a variety of enantioselectivities. In the case of alcohol 1, the enantiomeric ratio (the E value) was increased by changing the acylating agent from vinyl acetate (E = 30) to vinyl butyrate (E = 156) and dropped substantially with longer acyl donors. With vinyl chloroacetate, the reaction rate was fast and the enantioselectivity was high (E = 89), whereas the resolution with vinyl trifluoroacetate resulted in a very poor enantioselectivity (E = 4). The bulky acylating agent, vinyl pivalate, gave a moderate enantioselectivity (E = 15). In the case of alcohol 4, the enantioselectivities were excellent (E > 142) except vinyl pivalate (E = 12). It is indicated that the acyl group transiently attached at the active site of the lipase acts as a stereochemical controller. The solvent effect is also described briefly. A clear correlation was observed between the E values and the log P values of the organic solvents; the smaller the log P value of the solvent, the higher the E value.

  DOI：

  10.1021/jo961144s
• 作为产物：
  描述：

  2-(2-Hydroxy-ethyl)-cyclopent-3-enol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以66%的产率得到2-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]cyclopent-3-en-1-ol
  参考文献：
  名称：

  Kinetic Resolution of Racemic 2-Substituted 3-Cyclopenten-1-ols by Lipase-Catalyzed Transesterifications:  A Rational Strategy To Improve Enantioselectivity

  摘要：

  The effect of the acyl group of acylating agents on the enantioselectivity in the Pseudomonas cepacia lipase-catalyzed acylations of racemic alcohols has been studied. 2-[(N,N-Dimethylcarbamoyl)methyl]-3-cyclopenten-1-ol (1) and 2-[2-(tert-butyldimethylsilyloxy)ethyl]-3-cyclopenten-1-ol (4) were resolved with a variety of enantioselectivities. In the case of alcohol 1, the enantiomeric ratio (the E value) was increased by changing the acylating agent from vinyl acetate (E = 30) to vinyl butyrate (E = 156) and dropped substantially with longer acyl donors. With vinyl chloroacetate, the reaction rate was fast and the enantioselectivity was high (E = 89), whereas the resolution with vinyl trifluoroacetate resulted in a very poor enantioselectivity (E = 4). The bulky acylating agent, vinyl pivalate, gave a moderate enantioselectivity (E = 15). In the case of alcohol 4, the enantioselectivities were excellent (E > 142) except vinyl pivalate (E = 12). It is indicated that the acyl group transiently attached at the active site of the lipase acts as a stereochemical controller. The solvent effect is also described briefly. A clear correlation was observed between the E values and the log P values of the organic solvents; the smaller the log P value of the solvent, the higher the E value.

  DOI：

  10.1021/jo961144s