(dichloro)(ethyl)(2-methylphenyl)silane | 159259-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (dichloro)(ethyl)(2-methylphenyl)silane
• 英文别名: Dichloro-ethyl-(2-methylphenyl)silane
• CAS: 159259-37-7
• 化学式: C₉H₁₂Cl₂Si
• 分子量: 219.186
• InChiKey: JJSMEUJVMAIGLT-UHFFFAOYSA-N

物化性质

• 沸点：
  241.4±9.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (dichloro)(ethyl)(2-methylphenyl)silane 、 alkaline earth salt of/the/ methylsulfuric acid 在 palladium diacetate potassium fluoride 、 三(2-呋喃基)膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 以82%的产率得到2’-甲基联苯-4-甲酸
  参考文献：
  名称：

  Solid phase cross-coupling reaction of aryl(halo)silanes with 4-iodobenzoic acid

  摘要：

  Aryl(alkyl)(halo)silanes undergo facile and efficient palladium catalyzed cross-coupling reaction with iodobenzoic acid tethered to the Wang resin. Acid cleavage releases unsymmetrical biaryl carboxylic acids with high conversions, purities and yields. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00664-7
• 作为产物：
  描述：

  乙基三氯硅烷 、 2-溴甲苯 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到(dichloro)(ethyl)(2-methylphenyl)silane
  参考文献：
  名称：

  Solid phase cross-coupling reaction of aryl(halo)silanes with 4-iodobenzoic acid

  摘要：

  Aryl(alkyl)(halo)silanes undergo facile and efficient palladium catalyzed cross-coupling reaction with iodobenzoic acid tethered to the Wang resin. Acid cleavage releases unsymmetrical biaryl carboxylic acids with high conversions, purities and yields. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00664-7

文献信息

• Highly selective cross-coupling reactions of aryl(halo)silanes with aryl halides: A general and practical route to functionalized biaryls
  作者：Yasuo Hatanaka、Ken-ichi Goda、Yoshinori Okahara、Tamejiro Hiyama

  DOI：10.1016/s0040-4020(01)85554-x

  日期：1994.1

  The palladium catalyzed cross-coupling reaction of aryl halides with aryl(halo)silanes (halogen= F, Cl) gives good yields of unsymmetrical biaryls and p-terphenyls. The reaction takes place smoothly in N,N-dimethylformamide in the presence of an appropriate palladium catalyst and potassium fluoride. Since this reaction is tolerant of a variety of reactive functional groups, highly functionalized 4,4'-, 3,4'-, 2,4'- and even sterically crowded 2,2'-disubstituted biaryls can be obtained in moderate to high yields. The synthetic utility of the method has been demonstrated by its application to a short synthesis of liquid crystals. Mechanistic aspects of transmetalation of an aryl(fluoro)silicate intermediate with a palladium complex are discussed on the basis of the substituent effects on the rate of the cross-coupling reactions.
• Hatanaka Yasuo, Goda Ken-ichi, Okahara Yoshinori, Hiyama Tamejiro, Tetrahedron, 50 (1994) N 28, S 8301-8316
  作者：Hatanaka Yasuo, Goda Ken-ichi, Okahara Yoshinori, Hiyama Tamejiro

  DOI：——

  日期：——