2,3,4,5,6,7,8,9-octahydro-1H-carbazole | 26727-32-2

• 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: 2,3,4,5,6,7,8,9-octahydro-1H-carbazole
• 英文别名: 1,2,3,4,5,6,7,8-octahydrocarbazole；1,2,3,4,5,6,7,8-octahydro-carbazole；1,2,3,4,5,6,7,8-Octahydro-carbazol；1,2,3,3,5,6,7,8-Octahydro-carbazol；1,2,3,4,5,6,7,8-Octahydrocarbazol
• CAS: 26727-32-2
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: BKHWUYCOIGYJIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  165-170 °C(Press: 15 Torr)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,3,4,5,6,7,8,9-octahydro-1H-carbazole 在 溶剂黄146 、 铂 作用下， 生成 十二氢咔唑
  参考文献：
  名称：

  Masamune, Nippon Kagaku Zasshi, 1952, vol. 73, p. 48

  摘要：

  DOI：
• 作为产物：
  描述：

  dicyclohexylidenehydrazine 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以95%的产率得到2,3,4,5,6,7,8,9-octahydro-1H-carbazole
  参考文献：
  名称：

  N-取代的哌啶-4-一嗪的Piloty-Robinson反应。3,6-二氮杂咔唑合成的新途径

  摘要：

  在Piloty-Robinson反应中研究了制备1,2,3,4,6,7,8,9-八氢-5H-吡咯并[3,2-c：4,5-c']二吡啶的可能性各种条件。提出了一种由2,8-二苯甲酰基-1,2,3,4合成芳族3,6-二氮咔唑（5H-吡咯并[3,2-c：4,5-c']二吡啶）的新方法通过Piloty-Robinson方法在热条件下首次获得的6,7,8,9-八氢-5H-吡咯并[3,2-c：4,5-c']二吡啶。

  DOI：

  10.1007/s10593-011-0802-4

文献信息

• Hydrogenation of arenes and N-heteroaromatic compounds over ruthenium nanoparticles on poly(4-vinylpyridine): a versatile catalyst operating by a substrate-dependent dual site mechanism
  作者：Minfeng Fang、Nataliya Machalaba、Roberto A. Sánchez-Delgado

  DOI：10.1039/c1dt10801h

  日期：——

  A nanostructured catalyst composed of Ru nanoparticles immobilized on poly(4-vinylpyridine) (PVPy) has been synthesized by NaBH4 reduction of RuCl3·3H2O in the presence of the polymer in methanol at room temperature. TEM measurements show well-dispersed Ru nanoparticles with an average diameter of 3.1 nm. Both powder XRD patterns and XPS data indicate that the Ru particles are predominantly in the zerovalent state. The new catalyst is efficient for the hydrogenation of a wide variety of aromatic hydrocarbons and N-heteroaromatic compounds representative of components of petroleum-derived fuels. The experimental data indicate the existence of two distinct active sites in the nanostructure that lead to two parallel hydrogenation pathways, one for simple aromatics involving conventional homolytic hydrogen splitting on Ru and a second one for N-heteroaromatics taking place via a novel heterolytic hydrogen activation on the catalyst surface, assisted by the basic pyridine groups of the support.

  通过在室温下将RuCl3·3H2O在聚(4-乙烯基吡啶)(PVPy)存在下用NaBH4还原于甲醇中，合成了一种由Ru纳米颗粒固定在PVPy上的纳米结构催化剂。TEM测量显示，平均直径为3.1 nm的良好分散Ru纳米颗粒。粉末XRD图谱和XPS数据显示，Ru颗粒主要处于零价态。这种新型催化剂对广泛芳香烃和代表石油衍生燃料成分的N-杂芳香化合物的氢化反应效率高。实验数据表明，纳米结构中存在两种不同的活性位点，导致两种平行的氢化途径，一种是对简单芳香烃，涉及Ru上的传统均裂氢裂解，另一种是对N-杂芳香化合物，通过催化剂表面上的新型异裂氢活化进行，得到了载体中碱性吡啶基团的辅助。
• A general synthesis of pyrroles from aldehydes and ketones
  作者：Jack E. Baldwin、Jeffrey C. Bottaro

  DOI：10.1039/c39820000624

  日期：——

  The azines of enolisable aldehydes and ketones are converted into pyrroles via thermal rearrangement of the derived benzoyl derivatives and subsequent hydrazinolysis of the resulting N-benzoylpyrroles.

  通过衍生的苯甲酰基衍生物的热重排和随后的所得N-苯甲酰基吡咯的肼解作用，可烯化的醛和酮的嗪被转化为吡咯。
• 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。
• Reduction of the indole ring system: synthesis of 4,5,6,7-tetrahydroindoles
  作者：Casey C. McComas、David L. Van Vranken

  DOI：10.1016/s0040-4039(99)01687-1

  日期：1999.11

  A general two-step procedure for the reduction of indoles to the corresponding 4,5,6,7-tetrahydroindoles has been developed. A regioselective Birch reduction followed by catalytic hydrogenation is employed to accomplish this transformation. Yields for the sensitive pyrrole products are typically between 40 and 50%. This method provides access to complex chiral pyrroles that cannot be readily prepared

  已经开发了将吲哚还原为相应的4,5,6,7-四氢吲哚的通用两步方法。使用区域选择性的桦木还原，然后进行催化氢化来完成该转化。敏感的吡咯产物的产率通常在40％至50％之间。该方法提供了难以通过其他方法制备的复杂手性吡咯的途径。
• Ruthenium nanoparticles supported on magnesium oxide: A versatile and recyclable dual-site catalyst for hydrogenation of mono- and poly-cyclic arenes, N-heteroaromatics, and S-heteroaromatics
  作者：Minfeng Fang、Roberto A. Sánchez-Delgado

  DOI：10.1016/j.jcat.2013.12.017

  日期：2014.3

  development of catalysts capable of promoting hydrogenation of aromatics while being resistant to poisoning by nitrogen- and sulfur-containing species is of much interest in connection with hydrotreating of fossil fuels. We report a catalyst composed of ruthenium nanoparticles supported on magnesia, designed to promote heterolytic hydrogen splitting and surface ionic hydrogenation pathways. The catalyst, prepared

  与化石燃料的加氢处理有关，能够开发能够促进芳族化合物加氢同时抵抗含氮和硫的物质中毒的催化剂的研究备受关注。我们报告了一种由负载在氧化镁上的钌纳米颗粒组成的催化剂，旨在促进杂化氢分裂和表面离子加氢途径。通过一锅法制备的催化剂可促进单环和多环芳烃以及代表化石燃料组分的N和S杂芳烃的氢化。特别重要的是，相对于其他已知的负载贵金属，该催化剂具有出色的活性和更广阔的底物范围，以及出色的可回收性和长催化剂寿命。根据我们的实验数据，