(2,2-Dichlor-vinyl)-trimethyl-silan | 18163-67-2

• 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-Dichlor-vinyl)-trimethyl-silan
• 英文别名: (2,2-Dichlorovinyl)trimethylsilane；2,2-dichloroethenyl(trimethyl)silane
• CAS: 18163-67-2
• 化学式: C₅H₁₀Cl₂Si
• 分子量: 169.126
• InChiKey: XJOUOIHQTUEEED-UHFFFAOYSA-N

物化性质

• 沸点：
  143.3 °C(Press: 744 Torr)
• 密度：
  1.0380 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (2,2-Dichlor-vinyl)-trimethyl-silan 在 二(三叔丁基膦)钯 、 Cl₂Pd(DPEphos) 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 (E)-trimethyl(2-phenylprop-1-en-1-yl)silane
  参考文献：
  名称：

  Pd-catalyzed selective tandem arylation–alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

  摘要：

  Trans-selective monoarylation of 1, 1-dibromo- and 1,1-dichloro-1-alkenes (1) can be achieved in > 80% yields and in > 98-99% stereo selectivity with arylzinc bromides in the presence of a catalytic amount of Cl2Pd(DPEphos) or Cl2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of (Z)-alpha-bromostyrenes (3) with alkylzincs in the presence of 2 mol% of Pd('Bu3P)(2) proceeds to give the corresponding 2 in >90% yields and in greater than or equal to98-99% stereoselectivity. Although somewhat less satisfactory, the use of Cl2Pd(DPEphos) permits a one-pot tandem arylation-alkylation. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2003.09.008
• 作为产物：
  描述：

  2,2-dichloro-1-trichlorosilylethylene 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2,2-Dichlor-vinyl)-trimethyl-silan
  参考文献：
  名称：

  Mironow; Leites, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1959, p. 2051;engl.Ausg.S.1957

  摘要：

  DOI：

文献信息

• Liquid-phase chlorination ofC-chlorovinylsilanes
  作者：V. G. Lakhtin、V. L. Ryabkov、A. V. Kisin、V. M. Nosova、M. V. Polyakova、E. A. Chernyshev

  DOI：10.1007/bf00696724

  日期：1995.11

  Liquid-phase chlorination of a number of chloro(chlorovinyl)methylsilanes was investigated. A number of novelC-chlorosilanes were characterized by IR and1H NMR spectra. Some regularities of these reactions were determined; correlations between the structure of chloro(chlorovinyl)methylsilanes and their reactivities were identified.

  研究了许多氯（氯乙烯基）甲基硅烷的液相氯化。许多新型 C-氯硅烷通过 IR 和 1 H NMR 光谱进行了表征。确定了这些反应的一些规律；确定了氯（氯乙烯基）甲基硅烷的结构与其反应性之间的相关性。
• Petrow et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 1393; engl. Ausg. S. 1411
  作者：Petrow et al.

  DOI：——

  日期：——
• Reactions of chlorinated vinylsilanes with hydrogen chloride
  作者：V. G. Lakhtin、V. L. Ryabkov、A. V. Kisin、V. M. Nosova、E. A. Chernyshev

  DOI：10.1007/bf02494569

  日期：1999.2

  Catalytic hydrochlorination of a series of chloro(chlorovinyl)methylsilanes was studied. The course of the reaction depends on the number and position of the chlorine atoms in the initial monomers.
• Pd-catalyzed selective tandem arylation–alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives
  作者：Ji-cheng Shi、Ei-ichi Negishi

  DOI：10.1016/j.jorganchem.2003.09.008

  日期：2003.12

  Trans-selective monoarylation of 1, 1-dibromo- and 1,1-dichloro-1-alkenes (1) can be achieved in > 80% yields and in > 98-99% stereo selectivity with arylzinc bromides in the presence of a catalytic amount of Cl2Pd(DPEphos) or Cl2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of (Z)-alpha-bromostyrenes (3) with alkylzincs in the presence of 2 mol% of Pd('Bu3P)(2) proceeds to give the corresponding 2 in >90% yields and in greater than or equal to98-99% stereoselectivity. Although somewhat less satisfactory, the use of Cl2Pd(DPEphos) permits a one-pot tandem arylation-alkylation. (C) 2003 Elsevier B.V. All rights reserved.
• Mironow; Leites, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1959, p. 2051;engl.Ausg.S.1957
  作者：Mironow、Leites

  DOI：——

  日期：——