2-methyl-4,5,6,7-tetrahydro-1H-indole | 90642-57-2

• 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: 2-methyl-4,5,6,7-tetrahydro-1H-indole
• 英文别名: 2-Methyl-4,5,6,7-tetrahydroindole
• CAS: 90642-57-2
• 化学式: C₉H₁₃N
• 分子量: 135.209
• InChiKey: FVKONMYOYYXZAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  96 °C(Press: 2 Torr)
• 密度：
  1.0063 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-methyl-4,5,6,7-tetrahydro-1H-indole 在 异戊醇 、 sodium 作用下， 生成 2-methyl-2,3,4,5,6,7-hexahydro-indole
  参考文献：
  名称：

  Hadano; Matsuno, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1928, vol. 48, p. 111

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-bromoallyl)cyclohexanone 在 copper(l) iodide 、 N,N-二甲基甘氨酸盐酸盐 乙酸铵 、 potassium phosphate 、 叔丁胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以87%的产率得到2-methyl-4,5,6,7-tetrahydro-1H-indole
  参考文献：
  名称：

  Synthesis of Pyrroles via Copper-Catalyzed Coupling of Amines with Bromoenones

  摘要：

  在 K3PO4 和 NH4OAc 的存在下，CuI/N,N-二甲基甘氨酸盐酸盐催化了胺与δ-溴代δ,δ-不饱和酮的反应，生成了相应的多代吡咯，收率从良好到极佳。

  DOI：

  10.1055/s-2007-965980

文献信息

• Nitrogen Fixation: Synthesis of Heterocycles Using Molecular Nitrogen as a Nitrogen Source
  作者：Miwako Mori、Masaya Akashi、Masanori Hori、Katsutoshi Hori、Mayumi Nishida、Yoshihiro Sato

  DOI：10.1246/bcsj.77.1655

  日期：2004.9

  Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium–nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(OiPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium–nitrogen complexes. Although the structures of the titanium–nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.

  过渡金属固氮是一个迷人的过程。我们之前已经报道过使用Yamamoto报道的钛-氮配合物将分子氮引入有机化合物的方法。我们开发了一种新的钛催化氮化过程，使用TiCl4在过量Li和TMSCl的存在下进行。在这种反应中，可以使用1大气压的氮气，反应在室温下进行。这个过程非常简单。将TiCl4或Ti(OiPr)4（1 equiv.）、Li（10 equiv.）和TMSCl（10 equiv.）的THF溶液在氮气气氛下在室温下搅拌过夜，得到钛-氮配合物。尽管钛-氮配合物的结构尚未确定，但它们可能由N(TMS)3、X2TiN(TMS)2和XTi=NTMS组成。使用这种方法，可以通过钛配合物作为定量反应的单锅反应，以良好至中等的收率合成各种杂环化合物，如吲哚、喹啉、吡咯、吡咯啉和吲哚啉衍生物。此外，使用分子氮作为氮源合成了monomorine I和pumiliotoxin C。这种方法进一步扩展，用于使用催化量的钛配合物合成杂环化合物；此外，以高收率获得了吲哚和吡咯衍生物。
• A new synthetic aspect of acetic nitronic anhydrides
  作者：Masaaki Miyashita、Bahlul Z.E. Awen、Akira Yoshikoshi

  DOI：10.1016/s0040-4020(01)89068-2

  日期：1990.1

  A facile and convenient synthesis of acetic nitronic anhydrides from aliphatic nitroalkenes and lithium ketone enolates and the efficient conversion of these anhydrides to 1,4-diketones, alkylpyrroles, diketone monooximes, dihydro-1,2-oxazines, pyrrolidines, 2-hydroxypyrrolidines, and 1-pyrrolines are recorded.

  从脂肪族硝基烯烃和酮酸锂烯醇化物轻松便捷地合成乙酸硝基酸酐，并将这些酸酐有效转化为1,4-二酮，烷基吡咯，二酮一肟，二氢-1,2-恶嗪，吡咯烷，2-羟基吡咯烷和记录1-吡咯啉。
• Regioselective Synthesis of 2,3,4- or 2,3,5-Trisubstituted Pyrroles via [3,3] or [1,3] Rearrangements of <i>O</i>-Vinyl Oximes
  作者：Heng-Yen Wang、Daniel S. Mueller、Rachna M. Sachwani、Rachel Kapadia、Hannah N. Londino、Laura L. Anderson

  DOI：10.1021/jo200061b

  日期：2011.5.6

  base. When enolization is favored, a [3,3] rearrangement followed by a Paal-Knorr cyclization provides a 2,3,4-trisubstituted pyrrole; when enolization is disfavored, a [1,3] rearrangement occurs prior to enolization to produce a 2,3,5-trisubstituted pyrrole after cyclization. Optimization and scope of the O-allyl oxime isomerization and subsequent pyrrole formation are discussed and mechanistic pathways

  2,3,4-或2,3,5-三取代的吡咯的区域选择性合成分别通过O-乙烯基肟的[3,3]和[1,3]σ向重排实现。易于制备的O-烯丙基肟的铱催化异构化作用使得能够快速获得O-乙烯基肟。吡咯形成的区域选择性可以通过α-取代基的身份或通过添加胺碱来控制。当需要烯醇化时，先进行[3,3]重排，然后进行Paal-Knorr环化，即可得到2,3,4-三取代的吡咯；当烯醇化不利时，在烯醇化之前会发生[1,3]重排，从而在环化后产生2,3,5-三取代的吡咯。O的优化和范围讨论了烯丙基肟的异构化和随后吡咯的形成，并提出了机理。提供了选择带有β-酯O-烯丙基肟底物的[3,3]重排或[1,3]重排产物的条件。
• NITROGEN-CONTAINING FUSED RING COMPOUND, NITROGEN-CONTAINING FUSED RING POLYMER, ORGANIC THIN FILM, AND ORGANIC THIN FILM ELEMENT
  申请人：Ie Yutaka

  公开号：US20130041123A1

  公开（公告）日：2013-02-14

  Nitrogen-containing fused ring compound having at least one structural unit selected from the group consisting of a structural unit represented by the formula (1-1) and a structural unit represented by the formula (1-2).

  含氮融合环化合物，其至少具有从由式(1-1)表示的结构单元和由式(1-2)表示的结构单元组成的群体中选择的一个结构单元。
• Palladium-Catalyzed Amino-Heck Reaction of γ,δ-Unsaturated Ketone <i>O</i>-Diethylphosphinyloximes: A New Synthesis of Substituted Pyrroles and Indoles
  作者：Jia-Liang Zhu*、Yu-Hui Chan

  DOI：10.1055/s-2008-1072728

  日期：2008.5

  starting materials for the intramolecular amino-Heck reactions. In the presence of a catalytic amount of Pd(PPh 3 ) 4 in DBU, cyclization reactions occurred preferentially via a 5- EXO fashion to afford a variety of 2-substituted 5-methyl-1 H-pyrroles and several indole derivatives in moderate to high yields.

  γ,δ-不饱和酮 O-二乙基膦肟很容易由相应的酮制备，用作分子内氨基-Heck 反应的起始材料。在 DBU 中存在催化量的 Pd(PPh 3 ) 4 时，环化反应优先通过 5-EXO 方式发生，以提供各种 2-取代的 5-甲基-1 H-吡咯和几种吲哚衍生物。高产量。