2-(三甲基硅烷基)苯甲腈 | 86863-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(三甲基硅烷基)苯甲腈
• 英文名称: 2-(trimethylsilyl)benzonitrile
• 英文别名: 2-Trimethlysilanylbenzonitrile；2-trimethylsilylbenzonitrile
• CAS: 86863-90-3
• 化学式: C₁₀H₁₃NSi
• mdl: MFCD09039083
• 分子量: 175.305
• InChiKey: FSTZAERATRQAGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为产物：
  描述：

  N-cumylbenzamide 在 吡啶 、 四甲基乙二胺 、 三氟甲磺酸酐 、 仲丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2-(三甲基硅烷基)苯甲腈
  参考文献：
  名称：

  N-Cumyl Benzamide, Sulfonamide, and Aryl O-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics

  摘要：

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.

  DOI：

  10.1021/ol990846b

文献信息

• In situ trapping of ortho lithiated benzenes containing electrophilic directing groups
  作者：Timothy D. Krizan、J. C. Martin

  DOI：10.1021/ja00357a034

  日期：1983.9

  Description du piegeage in situ, utilisant des pieges electrophiles: (chlorotrimethyl) silane, (dichlorodimethyl) silane, trimethoxyborane, des especes aryllithium derivees de la reaction d'une base encombree le tetramethyl-2,2,6,6 piperidinure de lithium avec des substrats tels que: benzonitriles, benzoates arylcetones et arylsulfones

  Du piegeage in situ, utilisant des piegeselectrophiles: (chlorotrimethyl) 硅烷, (dichlorodimethyl) 硅烷, 三甲氧基硼烷, des eseses aryllithiumderived de la reaction d'une base encombree le tetramethyl-2,2,6,6 piperidinure delithium avec des底物 tels que：苯甲腈、苯甲酸酯、芳基丙酮和芳砜
• Cyanide‐Free Cyanation of sp ² and sp‐Carbon Atoms by an Oxazole‐Based Masked CN Source Using Flow Microreactors
  作者：Brijesh M. Sharma、Arun V. Nikam、Santosh Lahore、Gwang‐Noh Ahn、Dong‐Pyo Kim

  DOI：10.1002/chem.202103777

  日期：2022.4.6

  desired cyano compounds with reasonably good yields in a four-step flow manner. A unique feature of this cyanation protocol in flow enables to cyanate a variety of sp2 and sp carbons to produce a broad spectrum of aryl acetonitrile. It is envisaged that the OxBA based cyanation would replace existing unstable and toxic approaches as well as non-toxic cyanation using two different sources of "C" and "N"

  这项工作报告了一种无氰连续流动工艺，用于将 sp2 和 sp 碳氰化以从 (5-methyl-2-phenyloxazol-4-yl) 硼酸 [OxBA] 试剂作为唯一来源合成芳基、乙烯基和炔属腈碳结合掩蔽-CN 源。无毒且稳定的 OxBA 试剂是通过溴恶唑的锂化-硼化，以及连续的 Suzuki-Miyaura 与芳基、乙烯基或炔属卤化物的交叉偶联和去掩蔽 [4+2]/retro-[4+2] 生成的以四步流动的方式成功完成了以相当好的收率得到所需氰基化合物的序列。这种氰化方案在流动中的一个独特特点是能够氰化各种 sp2 和 sp 碳以产生广谱的芳基乙腈。
• Generation and reaction of cyano-substituted aryllithium compounds using microreactors
  作者：Aiichiro Nagaki、Heejin Kim、Hirotsugu Usutani、Chika Matsuo、Jun-ichi Yoshida

  DOI：10.1039/b919325c

  日期：——

  microflow method for the generation and reactions of aryllithiums bearing a cyano group, including o-lithiobenzonitrile, m-lithiobenzonitrile and p-lithiobenzonitrile. The method was effective at much higher temperatures than are required for conventional macrobatch reactions, by virtue of rapid mixing, short residence time, and efficient temperature control. In addition, reactions of o-lithiobenzonitrile

  我们开发了一种微流方法，用于带有氰基的芳基锂的生成和反应，包括 邻硫代苄腈， 间-硫代苄腈 和 对-硫代苄腈。由于快速混合，短的停留时间和有效的温度控制，该方法在比常规大批量反应所需的温度高得多的温度下是有效的。另外，反应邻硫代苄腈 在集成的微流系统中，用羰基化合物先后用亲电试剂捕集所得的烷氧基锂。
• Novel silylation of aromatic nitriles via photo-induced electron transfer
  作者：Soichiro Kyushin、Yasushi Ehara、Yasuhiro Nakadaira、Mamoru Ohashi

  DOI：10.1039/c39890000279

  日期：——

  Photo-induced electron transfer reactions of hexamethyldisilane and aromatic nitriles have been examined; hexamethyldisilane acts as an effective σ-donor, and undergoes novel photochemical silylation of aromatic nitriles.

  已经研究了六甲基乙硅烷和芳族腈的光致电子转移反应。六甲基乙硅烷可作为有效的σ供体，并经历芳族腈的新型光化学甲硅烷基化反应。
• KRIZAN, T. D.;MARTIN, J. C., J. AMER. CHEM. SOC., 1983, 105, N 19, 6155-6157
  作者：KRIZAN, T. D.、MARTIN, J. C.

  DOI：——

  日期：——