1-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole | 169384-00-3

• 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-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole
• 英文别名: 1H-Pyrrolo[1,2-a]indole, 2,3-dihydro-1-methyl-；3-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole
• CAS: 169384-00-3
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: IKNSDMRGLFLBTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-溴吲哚 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 36.0h， 生成 1-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole
  参考文献：
  名称：

  合成中的杂芳基：2-溴吲哚的自由基环化反应

  摘要：

  描述了带有不饱和N-烷基的2-溴吲哚的合成和自由基环化。

  DOI：

  10.1016/s0040-4020(97)10423-9

文献信息

• Palladium-Catalyzed, Ring-Forming Aromatic C–H Alkylations with Unactivated Alkyl Halides
  作者：Alexander R. O. Venning、Patrick T. Bohan、Erik J. Alexanian

  DOI：10.1021/jacs.5b01365

  日期：2015.3.25

  using unactivated alkyl halides and a variety of arenes and heteroarenes is described. This ring-forming process is successful with a variety of unactivated primary and secondary alkyl halides, including those with β-hydrogens. In contrast to standard polar or radical cyclizations of aromatic systems, electronic activation of the substrate is not required. The mild, catalytic reaction conditions are highly

  描述了使用未活化的烷基卤化物和各种芳烃和杂芳烃的催化 CH 烷基化。这种成环过程适用于各种未活化的伯和仲烷基卤化物，包括具有 β-氢的那些。与芳香系统的标准极性或自由基环化相比，不需要底物的电子活化。温和的催化反应条件具有高度的官能团耐受性，有助于获得各种合成和医学上重要的碳环和杂环系统。
• Nickel-catalyzed, ring-forming aromatic C–H alkylations with unactivated alkyl halides
  作者：Quentin D. Tercenio、Erik J. Alexanian

  DOI：10.1016/j.tet.2019.05.047

  日期：2019.8

  alkylation of aromatic substrates with unactivated alkyl halides is described. This carbocyclization facilitates the synthesis of diverse fused ring systems from simple aromatic substrates and is an attractive alternative to traditional polar or radical-mediated ring formations. The present system uses unactivated primary and secondary alkyl bromides and chlorides, while avoiding the use of precious palladium

  描述了镍催化芳香族底物与未活化的烷基卤化物的 C-H 烷基化反应的发展。这种碳环化促进了从简单的芳香族底物合成多种稠合环系统，并且是传统极性或自由基介导的环形成的有吸引力的替代方案。本系统使用未活化的伯和仲烷基溴和氯化物，同时避免使用贵重的钯催化剂和相关C-H烷基化中常用的反应性更强的烷基卤。
• Indole radical cyclisations: a rapid route to mitosenes
  作者：Adrian P. Dobbs、Keith Jones、Ken T. Veal

  DOI：10.1016/0040-4039(95)00838-4

  日期：1995.7

  The syntheses and radical cyclisations of 2-bromoindoles carrying an unsaturated N-alkyl group is described.

  描述了带有不饱和N-烷基的2-溴吲哚的合成和自由基环化。
• General and Efficient Approaches to Fused [1,2-<i>a</i>]Pyrroles and [1,2-<i>a</i>]Indoles
  作者：Alan R. Katritzky、Clara N. Fali、Jianqing Li

  DOI：10.1021/jo9623191

  日期：1997.6.13

  2-[(Benzotriazol-1-yl)methyl]pyrroles 4a-c, and 15a,b and -indoles 23, prepared as previously reported,(1,2) were converted into the corresponding fused [1,2-a]pyrroles 8a-c, and 18a,b and fused [1,2-a]indoles 25, 27 by intramolecular cyclizations; the formations of 25 and 27 involve [3 + 2] and [3 + 3] annulations. The benzotriazoly-CH-ring moieties of intermediates 8a,b, 18a,b, 25, and 27 were further elaborated: (i) acylation of 8a and subsequent reduction and elimination promoted by LiAlH4 to give product 6; (ii) nucleophilic displacements of the benzotriazolyl moiety with NaCN, NaSPh, and Grignard reagents to afford compounds 9, 11, 12, 20, 29, and 32, respectively; (iii) base-assisted eliminations of benzotriazole from 8b and 18a to form the unsaturated fused [1,2-a]pyrroles 10 and 17; (iv) reactions of 18b and 25 with alpha,beta-unsaturated ketone and aldehyde followed by acid-assisted elimination of the benzotriazolyl group to yield tricyclic compound 21 and product 31; and (v) Lewis acid promoted dimerization of 27 to form the fused indolo[3,2-b]carbazole 33.
• Heteroaryl radicals in synthesis: Radical cyclisation reactions of 2-bromoindoles
  作者：Adrian P. Dobbs、Keith Jones、Ken T. Veal

  DOI：10.1016/s0040-4020(97)10423-9

  日期：1998.3

  The synthesis and radical cyclisations of 2-bromoindoles carrying an unsaturated N-alkyl group is described.

  描述了带有不饱和N-烷基的2-溴吲哚的合成和自由基环化。

表征谱图