4-(trimethylsilyl)benzoic acid ethyl ester | 18028-09-6

• 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-(trimethylsilyl)benzoic acid ethyl ester
• 英文别名: ethyl p-(trimethylsilyl)benzoate；me3Si(ph-4-COOet)；4-trimethylsilanyl-benzoic acid ethyl ester；4-Trimethylsilyl-benzoesaeure-aethylester；ethyl p-trimethylsilylbenzoate；p-Trimethylsilyl-benzoesaeure-ethylester；Ethyl 4-trimethylsilylbenzoate
• CAS: 18028-09-6
• 化学式: C₁₂H₁₈O₂Si
• 分子量: 222.359
• InChiKey: MDXSTWMOMHCNDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 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

• 作为反应物：
  描述：

  4-(trimethylsilyl)benzoic acid ethyl ester 在 magnesium 、 乙酰氯 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 tris<4-(trimethylsilyl)phenyl>methyl chloride
  参考文献：
  名称：

  Substituent effect on the electrochemical oxidation of trityl anions. 2. Effect of an electron-withdrawing group

  摘要：

  DOI：

  10.1021/jo00320a003
• 作为产物：
  描述：

  1,4-二溴苯 在 magnesium 作用下， 反应 38.0h， 生成 4-(trimethylsilyl)benzoic acid ethyl ester
  参考文献：
  名称：

  Substituent effect on the electrochemical oxidation of trityl anions. 2. Effect of an electron-withdrawing group

  摘要：

  DOI：

  10.1021/jo00320a003

文献信息

• A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups
  作者：Aiichiro Nagaki、Heejin Kim、Yuya Moriwaki、Chika Matsuo、Jun-ichi Yoshida

  DOI：10.1002/chem.201000876

  日期：——

  A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para‐, meta‐, and ortho‐positions. Alkyl p‐ and m‐lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting

  由微混合器和微管反应器组成的流动微反应器系统为在对位，间位和邻位带有烷氧羰基的芳基锂的生成和反应提供了有效的工具。烷基p和-米通过与PhLi的I /锂交换反应生成-lithiobenzoates。与s BuLi的Br / Li交换反应不成功。所得芳基锂与亲电试剂的随后反应以良好收率得到所需产物。在另一方面，烷基ö -lithiobenzoates成功通过用溴/锂交换反应生成的小号卜力 随后与亲电试剂的反应以高收率得到所需产物。
• Design, Synthesis, and Implementation of Sodium Silylsilanolates as Silyl Transfer Reagents
  作者：Hiroki Yamagishi、Hayate Saito、Jun Shimokawa、Hideki Yorimitsu

  DOI：10.1021/acscatal.1c02733

  日期：2021.8.20

  There is an increasing demand for facile delivery of silyl groups onto organic bioactive molecules. One of the common methods of silylation via a transition-metal-catalyzed coupling reaction employs hydrosilane, disilane, and silylborane as major silicon sources. However, the labile nature of the reagents or harsh reaction conditions sometimes render them inadequate for the purpose. Thus, a more versatile

  对将甲硅烷基轻松传递到有机生物活性分子上的需求不断增加。通过过渡金属催化偶联反应进行硅烷化的一种常用方法是使用氢硅烷、乙硅烷和甲硅烷基硼烷作为主要的硅源。然而，试剂的不稳定性质或苛刻的反应条件有时使其不适合该目的。因此，需要更通用的甲硅烷基替代来源。我们在此报告了可储存的甲硅烷基硅烷醇钠的设计、合成和实施，该钠可用于在钯催化剂存在下芳基卤化物和拟卤化物的甲硅烷基化。所开发的方法允许对具有各种甲硅烷基的多官能化合物进行后期官能化。
• Diphenylphosphinophenolate: a ligand for the palladium-catalysed silylation of aryl halides activating simultaneously both palladium and silicon
  作者：Eiji Shirakawa、Takuya Kurahashi、Hiroto Yoshida、Tamejiro Hiyama

  DOI：10.1039/b006165o

  日期：——

  Diphenylphosphinophenolate was found to be an effective ligand for the palladium-catalysed silylation of aryl halides, activating not only palladium but also silicon of a disilane, where aryl bromides and iodides having such substituents as methyl, methoxy, amino, ethoxycarbonyl, trifluoromethyl, formyl or phenyl are applicable to the reaction with hexamethyldisilane to give the corresponding trimethylsilylarenes.

  二苯基膦酚酯被发现是一种有效的配体 对于钯催化的芳基卤化物的硅烷化，不仅活化 钯，还有乙硅烷的硅，其中芳基溴化物和碘化物 具有诸如甲基、甲氧基、氨基、乙氧基羰基等取代基， 三氟甲基、甲酰基或苯基适用于与 六甲基二硅烷生成相应的三甲基硅芳烃。
• The Electrical Effect of the Trimethylsilyl Group. II.
  作者：John D. Roberts、Clare M. Regan

  DOI：10.1021/ja01112a528

  日期：1953.8

  earlier investigation, we presented evidence based on Hammett σ-constants that the trimethylsilyl [(CH_3)_3Si-] group is electron-donating in character as judged by the manner in which it influences the acidity of the carboxyl group in benzoic acid. Since the electrical influence of the group is not apparently clear-cut in other types of compounds we have reinvestigated the reactivities of the trimethylsilyl

  在较早的调查中，我们提供了基于 Hammett σ 常数的证据，表明三甲基甲硅烷基 [(CH_3)_3Si-] 基团具有供电子特性，根据它影响苯甲酸中羧基酸度的方式来判断。由于该基团的电影响在其他类型的化合物中并不明显，我们重新研究了三甲基甲硅烷基取代的苯甲酸的反应性，并制备了相应的乙酯并确定了它们的碱性皂化率。
• Diphenylsilylsilanolates Enable the Transfer of a Wide Range of Silyl Groups
  作者：Hiroki Yamagishi、Fuyuki Harata、Jun Shimokawa、Hideki Yorimitsu

  DOI：10.1021/acs.orglett.2c03558

  日期：2023.1.13

  Development of silylating reagents that can transfer a wide range of silyl groups has been a long-standing challenge. Herein we report sodium diphenylsilylsilanolates as new stable and handy silylating reagents that could be synthesized from chlorosilanes. The new reagents retain the ability of dimethylsilylsilanolates for the delivery of a variety of silyl groups in palladium-catalyzed silylation

  开发可转移多种甲硅烷基的甲硅烷基化试剂一直是一项长期挑战。在这里，我们报告了二苯基甲硅烷基硅烷醇钠作为新型稳定且方便的甲硅烷基化试剂，可以从氯硅烷合成。新试剂保留了二甲基甲硅烷基硅烷醇盐在钯催化的芳基溴甲硅烷基化反应中传递各种甲硅烷基的能力，而不管要转移的甲硅烷基的空间和电子特性如何。