1-Boc-2-三甲基锡吲哚 | 146337-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-Boc-2-三甲基锡吲哚
• 英文名称: tert-butyl 2-(trimethylsilyl)-1H-indole-1-carboxylate
• 英文别名: tert-butyl 2-trimethylsilylindole-1-carboxylate
• CAS: 146337-49-7
• 化学式: C₁₆H₂₃NO₂Si
• 分子量: 289.45
• InChiKey: ABGOFOVJJKPFNA-UHFFFAOYSA-N

物化性质

• 沸点：
  373.6±34.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-Boc-2-三甲基锡吲哚 以 二甲基亚砜 为溶剂， 反应 2.0h， 以482.3 mg的产率得到2-(trimethylsilyl)-1H-indole
  参考文献：
  名称：

  Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes

  摘要：

  Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.

  DOI：

  10.1021/acs.orglett.0c02526
• 作为产物：
  描述：

  1-(tert-butyl)-2-(trimethylsilyl)diazene 、 1-Boc-吲哚 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到1-Boc-2-三甲基锡吲哚
  参考文献：
  名称：

  未活化的 C(sp2)-H 键与叔丁基取代的甲硅烷基二氮烯的无过渡金属甲硅烷基化

  摘要：

  带有 C(sp 2 )-Si 键的芳族有机硅烷在化学科学中的应用越来越多，但主要是通过原子不经济的化学计量程序生产的。还描述了使用氢硅烷作为硅源的催化替代品，但它们显示出不利的热力学，并且主要基于昂贵的催化系统，通常源自贵金属，或缺乏通用性。在此，我们描述了替代硅源的使用，即叔丁基取代的甲硅烷基二氮烯 ( t Bu-N=N-SiR 3 )，它很容易从市售前体中获得，并且其结构使 C(sp 2)-H 键硅烷化未活化的杂芳基和芳基化合物在无过渡金属的环境催化条件下。

  DOI：

  10.1021/acscatal.1c03824

文献信息

• Direct Access to α,β-Unsaturated Ketones via Rh/MgCl₂-Mediated Acylation of Vinylsilanes
  作者：Xue-Zu Deng、Zi-Yan Chen、Yang Song、Fei Xue、Motoki Yamane、Yan-Ni Yue

  DOI：10.1021/acs.joc.1c01205

  日期：2021.9.17

  We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized

  我们在此报告了通过铑催化的乙烯基硅烷与易得且丰富的羧酸的直接酰化来构建 α,β-不饱和酮的简便实用的结构。该协议的特点是可以访问各种综合有用的功能，并具有中等至出色的产量。更重要的是，药物的后期功能化也以合成有用的产率实现。
• Visible light mediated desilylative C(sp²)–C(sp²) cross-coupling reactions of arylsilanes with aryldiazonium salts under Au(<scp>i</scp>)/Au(<scp>iii</scp>) catalysis
  作者：Indradweep Chakrabarty、Manjur O. Akram、Suprakash Biswas、Nitin T. Patil

  DOI：10.1039/c8cc03925a

  日期：——

  Desilylative C(sp2)–C(sp2) cross-coupling reactions of arylsilanes with aryldiazonium salts under Au(I)/photoredox catalysis have been reported. The addition of Cu-salts as catalysts was found to be crucial for the success of this transformation.

  已经报道了在Au（I）/光氧化还原催化下，芳基硅烷与芳基重氮盐的脱甲硅基C（sp 2）-C（sp 2）交叉偶联反应。发现添加铜盐作为催化剂对于该转化的成功至关重要。
• .alpha.-Lithioamine synthetic equivalents: syntheses of diastereoisomers from Boc derivatives of cyclic amines
  作者：Peter Beak、Won Koo Lee

  DOI：10.1021/jo00057a024

  日期：1993.2

  Sequences of alpha'-lithiations and electrophilic substitutions of Boc-pyrrolidines, Boc-piperidines, and Boc-hexahydroazepines that provide compounds which are substituted adjacent to nitrogen are reported, and the pathways of the reactions are discussed. By this methodology monosubstituted 2 and disubstituted 2,4,2,6, and 2,5 Boc-piperidines are obtained as single or separable diastereoisomers consistent with equatorial lithiations and retentive electrophilic substitution in chair conformations. Both cis and trans 2,6-disubstituted diastereoisomers can be prepared, and control of diastereoselectivity is demonstrated by syntheses of solenopsin A, a 2,6-trans-disubstituted piperidine, and of Boc-dihydropinidine, a 2,6-cis-disubstituted piperidine. In the case of 3-methoxy-Boc-piperidine elimination of methoxide occurs upon lithiation, and with cis-2,4-disubstituted Boc-piperidines the electrophile is introduced with trans stereochemistry at C-6. These reactions are suggested to involve twist boat conformations consistent with an X-ray crystal structure of 2-methyl-6-(trimethylstannyl)-4-phenyl-N-Boc-piperidine. Boc-pyrrolidine lithiates more rapidly than Boc-piperidine, provides 2-substituted products with electrophiles, and on further lithiation-substitution gives 2,5-cis- and -trans-substituted products. Boc-perhydroazepine provides 2-substituted products by the sequence and on further lithiation-substitution gives 2,7-trans-disubstituted products.