4-trimethylsilylmethylbenzoic acid methyl ester | 99192-55-9

• 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: 4-trimethylsilylmethylbenzoic acid methyl ester
• 英文别名: Methyl 4-[(trimethylsilyl)methyl]benzoate；methyl 4-(trimethylsilylmethyl)benzoate
• CAS: 99192-55-9
• 化学式: C₁₂H₁₈O₂Si
• 分子量: 222.359
• InChiKey: GMZSCERCXPVZKL-UHFFFAOYSA-N

物化性质

• 沸点：
  275.2±23.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 4-溴甲基苯甲酸甲酯 在 四乙基对甲苯磺酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49%的产率得到4-trimethylsilylmethylbenzoic acid methyl ester
  参考文献：
  名称：

  AN ELECTROREDUCTIVE SYNTHESIS OF ALLYLSILANES AND BENZYLSILANES

  摘要：

  在氯三甲基硅烷存在下，苄基和烯丙基卤化物的电化学还原反应得到相应的苄基硅烷和烯丙基硅烷，产率令人满意。

  DOI：

  10.1246/cl.1985.463

文献信息

• Nickel-catalyzed coupling reaction of lithium organoborates and aryl mesylates possessing an electron withdrawing group
  作者：Yuichi Kobayashi、Ryo Mizojiri

  DOI：10.1016/0040-4039(96)01984-3

  日期：1996.11

  In the presence of NiCl2(PPh3)2 as catalyst, p-methoxycarbonylphenyl mesylate (5) and tosylate (6) react with lithium arylborates 4 (Ar = 2-furyl, Ph, p-Me-Ph; p-Me-Ph) at room temperature to afford the coupling products in high yields. Similarly, mesylates 9–11 coupled with these borates 4 efficiently.

  在作为催化剂的NiCl 2（PPh 3）2存在下，对甲氧基羰基苯基甲磺酸酯（5）和甲苯磺酸酯（6）与芳基硼酸锂4（Ar = 2-呋喃基，Ph，p-Me-Ph; p-Me-在室温下，以高收率获得偶联产物。同样，甲磺酸盐9-11与这些硼酸盐4高效结合。
• Rhodium-Catalyzed Silylation and Intramolecular Arylation of Nitriles via the Silicon-Assisted Cleavage of Carbon−Cyano Bonds
  作者：Mamoru Tobisu、Yusuke Kita、Yusuke Ano、Naoto Chatani

  DOI：10.1021/ja804992n

  日期：2008.11.26

  A rhodium-catalyzed silylation reaction of carbon-cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from eta(2)-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.
• AN ELECTROREDUCTIVE SYNTHESIS OF ALLYLSILANES AND BENZYLSILANES
  作者：Tatsuya Shono、Yoshihiro Matsumura、Susumu Katoh、Naoki Kise

  DOI：10.1246/cl.1985.463

  日期：1985.4.5

  The electrochemical reduction of benzyl and allyl halides carried out in the presence of chlorotrimethylsilane afforded the corresponding benzylsilanes and allylsilanes in satisfactory yields.

  在氯三甲基硅烷存在下，苄基和烯丙基卤化物的电化学还原反应得到相应的苄基硅烷和烯丙基硅烷，产率令人满意。