2-hexyl-1,2,3,4-tetrahydroquinoline | 1115387-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-hexyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-(n-hexyl)-1,2,3,4-tetrahydroquinoline
• CAS: 1115387-16-0
• 化学式: C₁₅H₂₃N
• 分子量: 217.354
• InChiKey: PFVXVBQMKHSJAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-hexylquinoline 在 C₂₆H₂₆ClN₂O₂RhS 、 sodium formate 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 2-hexyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  pH调节喹啉在水中的不对称转移加氢

  摘要：

  在缓冲水中，各种各样的喹啉衍生物在空气中以铑催化剂1和甲酸钠作为氢源进行不对称转移加氢，以提供具有重要对映选择性的重要合成1,2,3,4-四氢喹啉（参见方案； R = H，Me，F，Cl，Br，OMe； R'＝烷基，芳基）。

  DOI：

  10.1002/anie.200902570

文献信息

• The Remarkable Effect of a Simple Ion: Iodide-Promoted Transfer Hydrogenation of Heteroaromatics
  作者：Jianjun Wu、Chao Wang、Weijun Tang、Alan Pettman、Jianliang Xiao

  DOI：10.1002/chem.201201517

  日期：2012.7.27

  I can do it! Accelerated by simple iodide ions, rhodium‐catalysed transfer hydrogenation can be readily performed on quinolines, isoquinolines and quinoxalines, affording the tetrahydro products in high yields with low catalyst loading (see scheme).

  我能做到！通过简单的碘离子加速，铑催化的转移加氢反应可轻松地在喹啉，异喹啉和喹喔啉上进行，从而以高收率和低催化剂负载量提供四氢产物（参见方案）。
• pH-Regulated Asymmetric Transfer Hydrogenation of Quinolines in Water
  作者：Chao Wang、Chaoqun Li、Xiaofeng Wu、Alan Pettman、Jianliang Xiao

  DOI：10.1002/anie.200902570

  日期：2009.8.17

  In buffered water, a broad range of quinoline derivatives underwent asymmetric transfer hydrogenation in air with the rhodium catalyst 1 and sodium formate as the hydrogen source to furnish synthetically important 1,2,3,4‐tetrahydroquinolines with excellent enantioselectivities (see scheme; R=H, Me, F, Cl, Br, OMe; R′=alkyl, aryl).

  在缓冲水中，各种各样的喹啉衍生物在空气中以铑催化剂1和甲酸钠作为氢源进行不对称转移加氢，以提供具有重要对映选择性的重要合成1,2,3,4-四氢喹啉（参见方案； R = H，Me，F，Cl，Br，OMe； R'＝烷基，芳基）。
• Asymmetric Hydrogenation of Quinolines Catalyzed by Iridium Complexes of Monodentate BINOL-Derived Phosphoramidites
  作者：Nataša Mršić、Laurent Lefort、Jeroen A. F. Boogers、Adriaan J. Minnaard、Ben L. Feringa、Johannes G. de Vries

  DOI：10.1002/adsc.200800007

  日期：2008.5.5

  The monodentate BINOL-derived phosphoramidite PipPhos is used as ligand for the iridium-catalyzed asymmetric hydrogenation of 2- and 2,6-substituted quinolines. If tri-ortho-tolylphosphine and/or chloride salts are used as additives enantioselectivities are strongly enhanced up to 89%. NMR indicates that no mixed complexes are formed upon addition of tri-ortho-tolylphosphine.

  单齿BINOL衍生的亚磷酰胺PipPhos用作铱催化的2-和2,6-取代喹啉的不对称氢化的配体。如果使用三邻甲苯基膦和/或氯化物盐作为添加剂，对映选择性将大大提高至89％。NMR表明添加三邻甲苯基膦后没有形成混合的配合物。
• Selective Catalytic Hydrogenation of Heteroarenes with <i>N</i>-Graphene-Modified Cobalt Nanoparticles (Co₃O₄–Co/NGr@α-Al₂O₃)
  作者：Feng Chen、Annette-Enrica Surkus、Lin He、Marga-Martina Pohl、Jörg Radnik、Christoph Topf、Kathrin Junge、Matthias Beller

  DOI：10.1021/jacs.5b06496

  日期：2015.9.16

  Cobalt oxide/cobalt-based nanopartides featuring a core shell structure and nitrogen-doped graphene layers on alumina are obtained by pyrolysis of Co(OAc)(2)/phenanthroline. The resulting core shell material (Co3O4 Co/NGr@alpha-Al2O3) was successfully applied in the catalytic hydrogenation of a variety of N-heteroarenes including quinolines, acridines, benzo[h], and 1,5-naphthyridine as well as unprotected indoles. The peculiar structure of the novel heterogeneous catalyst enables activation of molecular hydrogen at comparably low temperature. Both high activity and selectivity were achieved in these hydrogenation processes, to give important building blocks for bioactive compounds as well as the pharmaceutical industry.
• <b>Benzimidazolylidene-Stabilized Borenium Ion for Catalytic Hydrogenation of N-Heterocycles</b>
  作者：Subir Maji、Pallavi Sarkar、Arpan Das、Swapan K Pati、Swadhin K. Mandal

  DOI：10.1021/acs.inorgchem.2c01841

  日期：2022.9.12

  borane adduct and its borenium ion. This borenium ion was used as a metal-free catalyst for hydrogenating various substituted quinoline N-heterocycles under ambient conditions. Furthermore, this method was utilized to synthesize two drug molecules: galipinine and angustureine. A detailed DFT study was performed to understand this metal-free catalytic hydrogenation.

  在此，我们报告了苯并咪唑亚基稳定的硼烷加合物及其硼鎓离子的合成。这种硼鎓离子用作无金属催化剂，用于在环境条件下氢化各种取代的喹啉 N-杂环。此外，该方法还用于合成两种药物分子：加利平和安古斯汀。进行了详细的 DFT 研究以了解这种无金属催化加氢。