(dichloro)(ethyl)(4-methylphenyl)silane | 135273-60-8

• 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)(4-methylphenyl)silane
• 英文别名: Dichloro(ethyl)(4-methylphenyl)silane；Dichloro-ethyl-(4-methylphenyl)silane
• CAS: 135273-60-8
• 化学式: C₉H₁₂Cl₂Si
• 分子量: 219.186
• InChiKey: FSSCRWFSYKXLHU-UHFFFAOYSA-N

物化性质

• 沸点：
  243.8±19.0 °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)(4-methylphenyl)silane 在 bis(η3-allyl-μ-chloropalladium(II)) potassium fluoride 、 三氟化锑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 1-甲氧基-2-(4-甲基苯基)苯
  参考文献：
  名称：

  Hatanaka, Yasuo; Fukushima, Satoshi; Hiyama, Tamejiro, Chemistry Letters, 1989, p. 1711 - 1714

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基三氯硅烷 、 对溴甲苯 在 magnesium 作用下， 生成 (dichloro)(ethyl)(4-methylphenyl)silane
  参考文献：
  名称：

  氟离子和钯催化剂促进有机氟硅烷与有机卤化物的羰基化偶联反应

  摘要：

  在氟离子和一氧化碳的大气压下，实现了有机氟硅烷与有机卤化物的钯催化羰基交叉偶联反应。烯基-或芳基氟硅烷与烯基或芳基碘化物有效地进行该反应，产率中等至良好。因此，在不保护反应性官能团例如醛，酮，酯，腈和醇的情况下，容易获得高度官能化的酮。为了顺利生成酮，必须使用有机氟硅烷。与芳基碘化物反应后，四芳基硅烷（如芳基（三甲基）硅烷）代替芳酰氟。

  DOI：

  10.1016/s0040-4020(01)88878-5

文献信息

• Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) Oxide
  作者：Kazunori Hirabayashi、Atsunori Mori、Jun Kawashima、Masahiro Suguro、Yasushi Nishihara、Tamejiro Hiyama

  DOI：10.1021/jo000679p

  日期：2000.8.1

  Palladium-catalyzed cross-coupling of aryl- or alkenylsilanols, silanediols, and silanetriols with a variety of iodoarenes by the catalysis of palladium(0) and in the presence of silver(I) oxide furnished the coupling products in good to excellent yields. The reactions of silanediols or silanetriols under similar conditions proceeded much faster than those of silanols to afford the corresponding coupling

  通过钯（0）的催化并在氧化银（I）的存在下，钯催化的芳基或链烯基硅烷醇，硅烷二醇和硅烷三醇与各种碘代芳烃的交叉偶联为偶联产物提供了良好或优异的收率。硅烷二醇或硅烷三醇在相似条件下的反应比硅烷醇的反应进行得快得多，从而可以在较短的反应时间内（5-12小时）以优异的产率提供相应的偶联产物。反应后银残余物的X射线衍射（XRD）图谱的测量表明，氧化银（I）被转化为碘化银（I）。
• Solid phase cross-coupling reaction of aryl(halo)silanes with 4-iodobenzoic acid
  作者：Fadi Homsi、Kazushi Hosoi、Kyoko Nozaki、Tamejiro Hiyama

  DOI：10.1016/s0022-328x(01)00664-7

  日期：2001.4

  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.
• 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.
• NaOH-Promoted cross-coupling reactions of organosilicon compounds with organic halides: Practical routes to biaryls, alkenylarenes and conjugated dienes
  作者：Emiko Hagiwara、Ken-ichi Gouda、Yasuo Hatanaka、Tamejiro Hiyama

  DOI：10.1016/s0040-4039(96)02320-9

  日期：1997.1

  The use of NaOH has been found to be extremely effective in promoting the palladium-catalyzed cross-coupling reactions of aryl and alkenylchlorosilanes with organic halides such as aryl bromides and chlorides under very mild conditions. Copyright (C) 1996 Elsevier Science Ltd
• Cross-Coupling Reactions of Aryl Chlorides with Organochlorosilanes:  Highly Effective Methods for Arylation or Alkenylation of Aryl Chlorides
  作者：Ken-ichi Gouda、Emiko Hagiwara、Yasuo Hatanaka、Tamejiro Hiyama

  DOI：10.1021/jo9611172

  日期：1996.1.1