N-ethyl-1,2,3,4,5,6,7,8-octahydrocarbazole | 861622-66-4

• 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: N-ethyl-1,2,3,4,5,6,7,8-octahydrocarbazole
• 英文别名: 9-ethyl-2,3,4,5,6,7,8,9-octahydrocarbazole；EOHC；N-Ethyl-1,2,3,4,5,6,7,8-octahydrocarbazol；9-ethyl-1,2,3,4,5,6,7,8-octahydro-carbazole；9-Aethyl-1,2,3,4,5,6,7,8-octahydro-carbazol；9-Ethyl-1,2,3,4,5,6,7,8-octahydrocarbazole
• CAS: 861622-66-4
• 化学式: C₁₄H₂₁N
• 分子量: 203.327
• InChiKey: SWLCQXGMRXJVKP-UHFFFAOYSA-N

物化性质

• 熔点：
  42.5 °C
• 沸点：
  327.1±11.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  N-ethyl-1,2,3,4,5,6,7,8-octahydrocarbazole 在 盐酸 、 tin 作用下， 生成 9-ethyl-1,2,3,4,4a,5,6,7,8,9a-decahydro-carbazole
  参考文献：
  名称：

  v. Braun; Ritter, Chemische Berichte, 1922, vol. 55, p. 3795

  摘要：

  DOI：
• 作为产物：
  描述：

  dodecahydro-N-ethylcarbazole 在 Ir(2,6-bis[di(i-propyl)phosphinomethyl]phenyl)H2 作用下， 反应 6.0h， 以34%的产率得到N-ethyl-1,2,3,4,5,6,7,8-octahydrocarbazole
  参考文献：
  名称：

  Dehydrogenation of N-ethyl perhydrocarbazole catalyzed by PCP pincer iridium complexes: Evaluation of a homogenous hydrogen storage system

  摘要：

  The iridium complexes IrH2{C6H3-2,6-(CH2PBu2t)(2) (1), IrH2{C6H3-2,6-(CH2PPr2i)(2) (2), and IrHCl{C6H3-2,6-(OPBu2t)(2) (3) have been found to be highly active catalysts for the dehydrogenation of N-ethyl perhydrocarbazole at 200 degrees C. However, dehydrogenation to the fully unsaturated ethyl carbazole does not occur in most instances. Complex 3 is the most active catalyst and shows reasonable activity even at 150 degrees C. No signs of dehydrogenation were found in experiments conducted at 100 degrees C. This apparently reflects the thermodynamic constraints imposed by the high enthalpy of dehydrogenation of the substrate. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.03.052

文献信息

• Solvent free selective dehydrogenation of indolic and carbazolic molecules with an iridium pincer catalyst
  作者：Daniel F. Brayton、Craig M. Jensen

  DOI：10.1039/c4cc02073a

  日期：——

  A previously known iridium POCOP pincer catalyst was found to selectively dehydrogenate the heterocyclic portion of several indolic and carbazolic molecules. These molecules were found to have an "activity window" (172-178 °C) upon which only the heterocyclic ring underwent dehydrogenation. All reactions were run solvent free, yields for selected substrates were excellent, and the products were isolated

  发现一种先前已知的铱POCOP夹钳催化剂选择性地使几个吲哚和咔唑分子的杂环部分脱氢。发现这些分子具有“活性窗口”（172-178℃），在该窗口上仅杂环经历了脱氢。所有反应均在无溶剂条件下进行，所选底物的收率非常好，并且通过蒸馏或氧化铝栓塞过滤分离了产物。
• PROCESS FOR PHOTOCATALYTIC ACCEPTOR-FREE DEHYDROGENATION OF HYDROCARBAZOLES AND HYDROINDOLES
  申请人：FRANKE Robert

  公开号：US20150239839A1

  公开（公告）日：2015-08-27

  A process for the photocatalytic acceptor-free dehydrogenation of hydrocarbazoles and hydroindoles is provided, wherein a hydrocarbazole or hydroindole is irradiated in the presence of a catalyst that is a rhodium complex containing organic phosphorus(III) compounds as ligands.

  提供了一种光催化无受体脱氢化氢咔唑和氢吲哚的方法，其中在存在催化剂的情况下，辐照氢咔唑或氢吲哚，所述催化剂为含有有机磷(III)化合物作为配体的铑配合物。
• Melting Points of Potential Liquid Organic Hydrogen Carrier Systems Consisting of <i>N</i>-Alkylcarbazoles
  作者：Katharina Stark、Philipp Keil、Sebastian Schug、Karsten Müller、Peter Wasserscheid、Wolfgang Arlt

  DOI：10.1021/acs.jced.5b00679

  日期：2016.4.14

  hydrogenation, the melting points of pure N-ethylcarbazole derivatives with increasing degree of hydrogenation as well as the liquidus line of the binary mixture of N-ethylcarbazole and N-ethyl-dodecahydro-carbazole were measured. Because of their structural and chemical resemblance binary mixtures consisting of different alkylcarbazole combinations were analyzed regarding their potential for a melting poi...

  液态有机氢载体 (LOHC) 代表了通过通常芳族化合物的氢化来储存氢的有吸引力的概念。研究得最好的 LOHC 之一是 N-乙基咔唑，因为它具有良好的热力学性质。然而，其 343.1 K 的高熔点可能是一个主要缺点，尤其是在移动应用中。因此，希望降低N-乙基咔唑的熔点而不显着改变有利的性能，例如载体化合物的储存密度或反应行为。为了研究加氢过程中的固液行为，测量了纯 N-乙基咔唑衍生物的熔点随加氢程度的增加以及 N-乙基咔唑和 N-乙基-十二氢-咔唑二元混合物的液相线。
• Verfahren zur photokatalytischen akzeptorfreien Dehydrierung von Hydrocarbazolen und Hydroindolen
  申请人：Evonik Degussa GmbH

  公开号：EP2910546A1

  公开（公告）日：2015-08-26

  Die Erfindung betrifft ein Verfahren zur photokatalytischen akzeptorfreien Dehydrierung von Hydrocarbazolen und Hydroindolen bei dem ein Hydrocarbazol oder Hydroindol in Gegenwart einer Rhodiumkomplexverbindung, die organische Phosphor(III)-Verbindungen als Liganden enthält, als Katalysator bestrahlt wird.

  本发明涉及一种烃咔唑和烃吲哚的光催化无受体脱氢工艺，在该工艺中，烃咔唑或烃吲哚作为催化剂，在含有有机磷（III）化合物作为配体的铑络合物存在下进行辐照。
• Method for measuring a degree of hydrogenation
  申请人：FRIEDRICH-ALEXANDER-UNIVERSITÄT ERLANGEN-NÜRNBERG

  公开号：US10359409B2

  公开（公告）日：2019-07-23

  A method for detecting a degree of hydrogenation of a liquid comprises one or more liquid hydrogen carriers, which can be hydrogenated, comprising: detecting a material property of the liquid and determining the degree of hydrogenation of the liquid on the basis of the detected material property of the liquid.

  一种检测液体氢化程度的方法包括一种或多种可被氢化的液态氢载体，该方法包括：检测液体的材料特性，并根据检测到的液体材料特性确定液体的氢化程度。