rac-(1-chloroethyl)dimethylphenylsilane | 17877-00-8

• 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: rac-(1-chloroethyl)dimethylphenylsilane
• 英文别名: (1-chloroethyl)dimethylphenylsilane；<2-Chlor-aethyl>-dimethyl-phenyl-silan；(1-Chloroethyl)(dimethyl)phenylsilane；1-chloroethyl-dimethyl-phenylsilane
• CAS: 17877-00-8
• 化学式: C₁₀H₁₅ClSi
• 分子量: 198.768
• InChiKey: ZRRIFLWTPREPSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  rac-(1-chloroethyl)dimethylphenylsilane 在 吡啶 、 4,6-二苯基噻吩[3,4-D]-1,3-二氧代-2-酮-5,5-二氧化物 、 氨 、 三乙胺 、 sodium iodide 作用下， 以 丙酮 为溶剂， 25.0~135.0 ℃ 、7.5 MPa 条件下， 反应 270.5h， 生成 rac-dimethylphenyl<1-(phenylacetamido)ethyl>silane
  参考文献：
  名称：

  Synthesis and enantioselective enzymatic hydrolysis of rac-dimethylphenyl[1-phenylacetamido)ethyl]silane

  摘要：

  Racemic dimethylphenyl[1-(phenylacetamido)ethyl]silane [rac-5] has been made by a four-step synthesis starting from (chloromethyl)dimethylphenylsilane [PhMe2SiCH2Cl (1) --> PhMe2SiCH(Cl)Me (rac-2) --> PhMe2SiCH(I)Me (rac-3) --> PhMe2SiCH(NH2)Me (rac-4) --> PhMe2SiCH[N(H)C(O)CH2Ph]Me (rac-5); total yield 41%]. Enantioselective enzymatic hydrolysis of rac-5, catalyzed by immobilized penicillin G acylase (E.C. 3.5.1.11) from Escherichia coli 5K (pHM 12), gave (R)-(1-aminoethyl)dimethylphenylsilane [(R)-4] in 40% yield with an enantiomeric purity of 92% ee.

  DOI：

  10.1016/0022-328x(91)83279-d
• 作为产物：
  描述：

  二甲基氯甲基苯基硅烷 、 碘甲烷 在 四甲基乙二胺 、 仲丁基锂 作用下， 生成 rac-(1-chloroethyl)dimethylphenylsilane
  参考文献：
  名称：

  Synthesis and enantioselective enzymatic hydrolysis of rac-dimethylphenyl[1-phenylacetamido)ethyl]silane

  摘要：

  Racemic dimethylphenyl[1-(phenylacetamido)ethyl]silane [rac-5] has been made by a four-step synthesis starting from (chloromethyl)dimethylphenylsilane [PhMe2SiCH2Cl (1) --> PhMe2SiCH(Cl)Me (rac-2) --> PhMe2SiCH(I)Me (rac-3) --> PhMe2SiCH(NH2)Me (rac-4) --> PhMe2SiCH[N(H)C(O)CH2Ph]Me (rac-5); total yield 41%]. Enantioselective enzymatic hydrolysis of rac-5, catalyzed by immobilized penicillin G acylase (E.C. 3.5.1.11) from Escherichia coli 5K (pHM 12), gave (R)-(1-aminoethyl)dimethylphenylsilane [(R)-4] in 40% yield with an enantiomeric purity of 92% ee.

  DOI：

  10.1016/0022-328x(91)83279-d

文献信息

• Use of a Novel α-Hydroxyethylating Reagent in the Stereoselective Synthesis of Lincosamine
  作者：Floris L. van Delft、Martin de Kort、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1021/jo951931+

  日期：1996.1.1
• Synthesis and enantioselective enzymatic hydrolysis of rac-dimethylphenyl[1-phenylacetamido)ethyl]silane
  作者：Heidi Hengelsberg、Reinhold Tacke、Kirsten Fritsche、Christoph Syldatk、Fritz Wagner

  DOI：10.1016/0022-328x(91)83279-d

  日期：1991.9

  Racemic dimethylphenyl[1-(phenylacetamido)ethyl]silane [rac-5] has been made by a four-step synthesis starting from (chloromethyl)dimethylphenylsilane [PhMe2SiCH2Cl (1) --> PhMe2SiCH(Cl)Me (rac-2) --> PhMe2SiCH(I)Me (rac-3) --> PhMe2SiCH(NH2)Me (rac-4) --> PhMe2SiCH[N(H)C(O)CH2Ph]Me (rac-5); total yield 41%]. Enantioselective enzymatic hydrolysis of rac-5, catalyzed by immobilized penicillin G acylase (E.C. 3.5.1.11) from Escherichia coli 5K (pHM 12), gave (R)-(1-aminoethyl)dimethylphenylsilane [(R)-4] in 40% yield with an enantiomeric purity of 92% ee.