2-ethyl-4,5,6,7-tetrahydro-1H-indole | 125405-80-3

• 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: 2-ethyl-4,5,6,7-tetrahydro-1H-indole
• CAS: 125405-80-3
• 化学式: C₁₀H₁₅N
• 分子量: 149.236
• InChiKey: HEHCRFARFOPQFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 锌铜偶 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以67%的产率得到2-ethyl-4,5,6,7-tetrahydro-1H-indole
  参考文献：
  名称：

  由酮和硝基烯烃方便而通用地合成聚烷基吡咯

  摘要：

  已经开发了一种方便且通用的方法，该方法通过还原中间体乙酸硝基酸酐，从酮和硝基烯烃开始合成聚烷基吡咯。

  DOI：

  10.1039/c39890000841

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。
• [EN] QUINOLONE COMPOUND<br/>[FR] COMPOSÉ QUINOLONE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2013029548A1

  公开（公告）日：2013-03-07

  The present invention provides a compound represented by the formula (I) wherein X is a hydrogen atom or a fluorine atom; R is a hydrogen atom or alkyl; R1 is (1) cyclopropyl optionally substituted by to 3 halogen atoms or (2) phenyl optionally substituted by 1 to 3 halogen atoms; R2 is alkyl, alkoxy, haloalkoxy, a halogen atom, cyano, etc.; and R3 is 7-oxo-7,8-dihydro-1,8-naphthyridinyl, 3-pyridyl, etc., or a salt thereof. The compound of the present invention has excellent antimicrobial activity against Clostridium difficile and is useful for the prevention or treatment of intestinal infection such as Clostridium difficile- associated diarrhea.

  本发明提供了一种化合物，其表示为式(I)，其中X为氢原子或氟原子；R为氢原子或烷基；R1为（1）环丙基，可选择地被1至3个卤原子取代，或（2）苯基，可选择地被1至3个卤原子取代；R2为烷基、烷氧基、卤代烷氧基、卤原子、氰基等；R3为7-氧代-7,8-二氢-1,8-萘啶基，3-吡啶基等，或其盐。本发明的化合物对厌氧菌艰难梭菌具有优异的抗菌活性，并可用于预防或治疗肠道感染，如厌氧菌艰难梭菌相关性腹泻。
• The synthesis of pyrroles via acceptorless dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols mediated by a robust and reusable catalyst based on nanometer-sized iridium particles
  作者：Daniel Forberg、Johannes Obenauf、Martin Friedrich、Sven-Martin Hühne、Werner Mader、Günter Motz、Rhett Kempe

  DOI：10.1039/c4cy01018c

  日期：——

  Pyrroles are important compounds with several applications in medicine and material science. They can be synthesized sustainably from secondary alcohols and amino alcohols. Hydrogen and water are liberated in the course of this reaction. Here, we present that this sustainable catalytic pyrrole synthesis can be mediated efficiently by a novel iridium nanoparticle catalyst. The catalyst synthesis starts

  吡咯是重要的化合物，在医学和材料科学中有多种应用。它们可以由仲醇和氨基醇可持续地合成。在该反应过程中释放出氢气和水。在这里，我们目前可以通过新型铱纳米粒子催化剂有效地介导这种可持续的催化吡咯合成。催化剂的合成从分子前体，N-配体稳定的Ir络合物和市售的聚硅氮烷开始。实现了纳米级铱粒子的生成（由于载体中存在N原子）。载体的坚固性质允许催化剂的再利用。通过合成23种吡咯衍生物（分离产率高达93％）验证了反应的范围。因此，有吸引力的官能团耐受性（例如胺和烯烃）。市售的非均相Ir催化剂在该吡咯合成中效率低下，并且在可重复使用性方面受到极大限制。
• Manganese-Catalyzed Sustainable Synthesis of Pyrroles from Alcohols and Amino Alcohols
  作者：Fabian Kallmeier、Beata Dudziec、Torsten Irrgang、Rhett Kempe

  DOI：10.1002/anie.201702543

  日期：2017.6.12

  can be obtained from indigestible biomass such as lignocellulose. The conservation of our rare noble metals is of similar importance, and their replacement by abundantly available transition metals, such as Mn, Fe, or Co (base or nonprecious metals), in key technologies such as catalysis is a promising option. Herein, we report on the first base‐metal‐catalyzed synthesis of pyrroles from alcohols and

  将醇转化为重要化合物的反应的发展节省了我们的化石碳资源，因为可以从不可消化的生物质（如木质纤维素）中获得醇。我们稀有贵金属的保护也具有相似的重要性，在催化等关键技术中，用大量可用的过渡金属（例如Mn，Fe或Co（贱金属或非贵金属）代替它们）是一种有前途的选择。在此，我们报道了由醇和氨基醇进行的第一种贱金属催化的吡咯合成。最有效的催化剂是由PN 5稳定的Mn络合物P配体，而相关的Fe和Co络合物则无活性。该反应在温和的条件下以低至0.5 mol％的催化剂负载量进行，具有广泛的范围和有吸引力的官能团耐受性。这些发现可能会启发其他人在挑战性的脱氢反应中使用锰催化剂代替Ir或Ru络合物。