(dichloro)(ethyl)(4-methoxyphenyl)silane | 130952-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (dichloro)(ethyl)(4-methoxyphenyl)silane
• 英文别名: dichloro-ethyl-(4-methoxyphenyl)silane
• CAS: 130952-94-2
• 化学式: C₉H₁₂Cl₂OSi
• 分子量: 235.185
• InChiKey: RAXCHOOUUHKMNT-UHFFFAOYSA-N

物化性质

• 沸点：
  268.0±23.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (dichloro)(ethyl)(4-methoxyphenyl)silane 在 四(三苯基膦)钯 、 水 、 苯胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.0h， 生成 4-甲氧基联苯
  参考文献：
  名称：

  氧化银（I）促进的钯催化的硅烷醇，硅烷二醇和硅烷三醇的交叉偶联

  摘要：

  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）。

  DOI：

  10.1021/jo000679p
• 作为产物：
  描述：

  4-溴苯甲醚 、 乙基三氯硅烷 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到(dichloro)(ethyl)(4-methoxyphenyl)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

• Synthesis of trifluoromethylamino-substituted pyridines and pyrimidines by oxidative desulfurization-fluorination
  作者：Manabu Kuroboshi、Katsuya Mizuno、Kiyoshi Kanie、Tamejiro Hiyama

  DOI：10.1016/0040-4039(94)02253-8

  日期：1995.1

  Oxidative desulfurization-fluorination of methyl N-pyridyl(or N-pyrimidyl)-N-alkyldithiocarbamates gave the corresponding trifluoromethylamino-substituted pyridines (or pyrimidines), which underwent cross-coupling reaction to give a new type of liquid crystalline compounds having trifluoromethylamino group.

  N-吡啶基甲基（或N-嘧啶基）-N-烷基二硫代氨基甲酸酯的氧化脱硫-氟化得到相应的三氟甲基氨基取代的吡啶（或嘧啶），其经历交叉偶联反应以得到具有三氟甲基氨基基团的新型液晶化合物。
• Silicone as an Organosilicon Reagent 2. Rhodium-catalyzed Conjugate Addition of the Silicone Reagent to α,β-Unsaturated Carbonyl Compounds
  作者：Tooru Koike、Xiaoli Du、Atsunori Mori、Kohtaro Osakada

  DOI：10.1055/s-2002-19787

  日期：——

  The reaction of poly(phenylmethylsiloxane) with α,β-unsaturated carbonyl compounds in the presence of aqueous K 2 CO 3 and 3 mol% of [Rh(OH)(cod)] 2 gives 1,4-conjugate addition product in good yields. Arylchlorosilanes also undergo the conjugate addition in excellent yields under similar conditions.

  聚（苯基甲基硅氧烷）与 α,β-不饱和羰基化合物在 K 2 CO 3 水溶液和 3 mol% [Rh(OH)(cod)] 2 的存在下反应，以良好的产率得到 1,4-共轭加成产物. 芳基氯硅烷也在类似条件下以优异的产率进行共轭加成。
• Syntheses and Properties of Novel Liquid Crystals Containing a Trifluoromethylamino Group
  作者：Kiyoshi Kanie、Katsuya Mizuno、Manabu Kuroboshi、Sadao Takehara、Tamejiro Hiyama

  DOI：10.1246/bcsj.72.2523

  日期：1999.11

  Liquid crystals (LCs) containing a trifluoromethylamino group are prepared by the cross-coupling reaction of p-bromo-substituted-(hetero)aryl(trifluoromethyl)amines that are derived from the corresponding dithiocarbamates through oxidative desulfurization–fluorination. The novel LCs are shown to exhibit mainly a smectic phase over a wide range of temperatures. Their electro-optical properties as a component of nematic LCs are compared with those of the corresponding methylamines.

  含三氟甲基氨基团的液晶（LCs）是通过 p-溴取代的（杂）芳基（三氟甲基）胺与相应的二硫氨基甲酸酯经过氧化脱硫–氟化反应的交叉偶联反应制备的。新型液晶在较宽的温度范围内主要表现出层状相。它们作为向列相液晶的组成部分，其电光性能与相应的甲基胺进行了比较。
• 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