1-(tert-Butyldimethylsilyl)-3-methylindole | 108939-97-5

• 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
• 英文名称: 1-(tert-Butyldimethylsilyl)-3-methylindole
• 英文别名: 1-(t-butyldimethylsilyl)-3-methylindole；1H-Indole, 1-[(1,1-dimethylethyl)dimethylsilyl]-3-methyl-；tert-butyl-dimethyl-(3-methylindol-1-yl)silane
• CAS: 108939-97-5
• 化学式: C₁₅H₂₃NSi
• 分子量: 245.44
• InChiKey: UNEHTEUZVKDUCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(tert-Butyldimethylsilyl)-3-methylindole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 3-甲基吲哚
  参考文献：
  名称：

  REGIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED INDOLES: 3-ETHYLINDOLE

  摘要：

  DOI：

  10.15227/orgsyn.074.0248
• 作为产物：
  描述：

  N-tert-butyldimethylsilylindole 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 1-(tert-Butyldimethylsilyl)-3-methylindole
  参考文献：
  名称：

  Preparation and reactions of 1-(tert-butyldimethylsilyl)-3-lithioindole. Regioselective synthesis of 3-substituted indoles

  摘要：

  DOI：

  10.1021/jo00080a004

文献信息

• Benzylic C(sp³)–C(sp²) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis
  作者：Weonjeong Kim、Jangwoo Koo、Hong Geun Lee

  DOI：10.1039/d0sc06666d

  日期：——

  effectively delivered from an aryl (pseudo)halide or an acid anhydride coupling partner, respectively. The developed method utilizes mild conditions and exhibits a wide substrate scope for both substituted indoles and C(sp2)-based reaction counterparts. Mechanistic studies have shown that competitive hydrogen atom transfer (HAT) processes, which are frequently encountered in conventional methods, are not

  基于吲哚底物的容易氧化事件，开发了一种机械上独特的苄基 C(sp 3 )-H 键功能化策略。这种新颖的途径是通过在底物的苄基位置上有效地产生自由基来启动的，随后通过过渡金属催化来完成整个转化。最终，芳基或酰基可以分别从芳基（拟）卤化物或酸酐偶联配偶体有效地传递。所开发的方法利用温和的条件，并对取代的吲哚和基于 C(sp 2 ) 的反应对应物表现出广泛的底物范围。机理研究表明，传统方法中经常遇到的竞争性氢原子转移（HAT）过程并不参与所开发策略的产物形成过程。
• Dearomative Indole Cycloaddition Reactions of Aza-Oxyallyl Cationic Intermediates: Modular Access to Pyrroloindolines
  作者：Arjun Acharya、Devendar Anumandla、Christopher S. Jeffrey

  DOI：10.1021/jacs.5b10184

  日期：2015.12.2

  A regioselective dearomative aza-(3 + 2) cycloaddition reaction of substituted indoles with α-halohydroxamates has been developed. This transformation provides rapid access to highly functionalized pyrroloindolines that are represented in large number of bioactive compounds. The natural product, physostigmine, has been concisely synthesized utilizing this method.

  已开发出取代吲哚与 α-卤代异羟肟酸酯的区域选择性脱芳香氮杂-(3 + 2) 环加成反应。这种转变提供了对以大量生物活性化合物为代表的高度官能化吡咯并二氢吲哚的快速获取。天然产物毒扁豆碱已使用该方法简明地合成。
• Oxidative (3 + 2) Cycloaddition Reactions of Diaza-Oxyallyl Cationic Intermediates and Indoles for the Synthesis of Imidazoloindolines
  作者：Devendar Anumandla、Arjun Acharya、Christopher S. Jeffrey

  DOI：10.1021/acs.orglett.5b03527

  日期：2016.2.5

  An oxidative diaza-(3 + 2) cycloaddition reaction of simple urea derivatives with substituted indoles has been developed. This transformation provides rapid access to highly functionalized imidazoloindolines that are represented in bioactive compounds. The reported method is compatible with a wide variety of functional groups and directly provides unique heterocyclic scaffolds from indoles and a simple

  已开发出简单的脲衍生物与取代的吲哚的氧化二氮杂-（3 + 2）环加成反应。这种转化使人们能够快速获得以生物活性化合物为代表的高度官能化的咪唑啉二啉。报道的方法与多种官能团兼容，并且直接提供了由吲哚和简单的尿素衍生物组成的独特的杂环骨架。
• Late-stage diversification of indole skeletons through nitrogen atom insertion
  作者：Julia C. Reisenbauer、Ori Green、Allegra Franchino、Patrick Finkelstein、Bill Morandi

  DOI：10.1126/science.add1383

  日期：2022.9.2

  Compared with peripheral late-stage transformations mainly focusing on carbon–hydrogen functionalizations, reliable strategies to directly edit the core skeleton of pharmaceutical lead compounds still remain scarce despite the recent flurry of activity in this area. Herein, we report the skeletal editing of indoles through nitrogen atom insertion, accessing the corresponding quinazoline or quinoxaline bioisosteres by trapping of an electrophilic nitrene species generated from ammonium carbamate and hypervalent iodine. This reactivity relies on the strategic use of a silyl group as a labile protecting group that can facilitate subsequent product release. The utility of this highly functional group-compatible methodology in the context of late-stage skeletal editing of several commercial drugs is demonstrated.

  与主要侧重于碳-氢官能化的外围后期转化相比，直接编辑药物先导化合物核心骨架的可靠策略仍然稀缺，尽管最近该领域的活动十分活跃。在此，我们报告了通过氮原子插入对吲哚进行骨架编辑的方法，通过捕获由氨基甲酸铵和高价碘生成的亲电烯类，获得相应的喹唑啉或喹喔啉生物异构体。这种反应性依赖于战略性地使用硅烷基作为易溶保护基团，从而促进后续产物的释放。这种高度兼容官能团的方法在几种商业药物的后期骨架编辑中的应用得到了证实。
• Asymmetric Synthesis of Indole Homo-Michael Adducts via Dynamic Kinetic Friedel–Crafts Alkylation with Cyclopropanes
  作者：Steven M. Wales、Morgan M. Walker、Jeffrey S. Johnson

  DOI：10.1021/ol4010646

  日期：2013.5.17

  An enantioconvergent Friedel-Crafts alkylation of indoles with donor-acceptor cyclopropanes is described. The reaction is catalyzed by pybox center dot Mgl(2) and proceeds via a type I dynamic kinetic asymmetric transformation (DyKAT).