2-[Dimethyl(phenyl)silyl]pent-3-ynyl 2-chloroacetate | 1246176-17-9

• 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-[Dimethyl(phenyl)silyl]pent-3-ynyl 2-chloroacetate
• CAS: 1246176-17-9
• 化学式: C₁₅H₁₉ClO₂Si
• 分子量: 294.853
• InChiKey: KFBVHHVCNJWJHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[Dimethyl(phenyl)silyl]pent-3-ynyl 2-chloroacetate 在 Lipase QLM 作用下， 以 丙酮 为溶剂， 反应 96.0h， 以43%的产率得到(2R)-2-[dimethyl(phenyl)silyl]pent-3-yn-1-ol
  参考文献：
  名称：

  Practical synthesis of (E)- and (Z)-2-silyl-3-penten-1-ols with high enantiopurity

  摘要：

  Practical methods for the synthesis of the optically active (E)- and (Z)-2-silyl-3-pentene-1-ols are described. The optically pure (E)-allylsilane was synthesized from commercially available (R)-3-butyn-2-ol in five steps involving hydrozirconation followed by alkylation of the resulting alkenylmetal with BnOCH2Cl. On the other hand, both enantiomers of the corresponding (Z)-allylsilane were prepared from commercially available dimethylphenylvinylsilane through epoxidation, the regioselective epoxide-opening reaction with 1-propynylmagnesium bromide, and the subsequent optical resolution using a lipase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.104
• 作为产物：
  描述：

  2-[Dimethyl(phenyl)silyl]pent-3-yn-1-ol 、 氯乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到2-[Dimethyl(phenyl)silyl]pent-3-ynyl 2-chloroacetate
  参考文献：
  名称：

  Practical synthesis of (E)- and (Z)-2-silyl-3-penten-1-ols with high enantiopurity

  摘要：

  Practical methods for the synthesis of the optically active (E)- and (Z)-2-silyl-3-pentene-1-ols are described. The optically pure (E)-allylsilane was synthesized from commercially available (R)-3-butyn-2-ol in five steps involving hydrozirconation followed by alkylation of the resulting alkenylmetal with BnOCH2Cl. On the other hand, both enantiomers of the corresponding (Z)-allylsilane were prepared from commercially available dimethylphenylvinylsilane through epoxidation, the regioselective epoxide-opening reaction with 1-propynylmagnesium bromide, and the subsequent optical resolution using a lipase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.104

文献信息

• Practical synthesis of (E)- and (Z)-2-silyl-3-penten-1-ols with high enantiopurity
  作者：Koichiro Fukuda、Masaaki Miyashita、Keiji Tanino

  DOI：10.1016/j.tetlet.2010.06.104

  日期：2010.8

  Practical methods for the synthesis of the optically active (E)- and (Z)-2-silyl-3-pentene-1-ols are described. The optically pure (E)-allylsilane was synthesized from commercially available (R)-3-butyn-2-ol in five steps involving hydrozirconation followed by alkylation of the resulting alkenylmetal with BnOCH2Cl. On the other hand, both enantiomers of the corresponding (Z)-allylsilane were prepared from commercially available dimethylphenylvinylsilane through epoxidation, the regioselective epoxide-opening reaction with 1-propynylmagnesium bromide, and the subsequent optical resolution using a lipase. (C) 2010 Elsevier Ltd. All rights reserved.