6-苯基-5,6,7,8-四氢喹啉 | 583871-10-7

• 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
• 中文名称: 6-苯基-5,6,7,8-四氢喹啉
• 英文名称: 6-phenyl-5,6,7,8-tetrahydroquinoline
• 英文别名: Quinoline, 5,6,7,8-tetrahydro-6-phenyl-
• CAS: 583871-10-7
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: BKWKYDPEPIAOQN-UHFFFAOYSA-N

物化性质

• 沸点：
  328.2±21.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-苯基环己酮 、 氨基乙腈 在 C₁₉H₁₅AuClN₂PS 、 silver trifluoromethanesulfonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以53%的产率得到6-苯基-5,6,7,8-四氢喹啉
  参考文献：
  名称：

  Au-complex containing phosphino and imidazolyl moieties as a bi-functional catalyst for one-pot synthesis of pyridine derivatives

  摘要：

  The complex of Au-L1 containing imidazolyl ring and the phosphine-ligated-Au moiety was synthesized and applied as the efficient bi-functional catalyst for the one-pot sequential condensation/annulation reaction for the synthesis of pyridine derivatives. It was found that, as for Au-L1, the involved imidazolyl group acted as a Lewis base to catalyze the condensation of carbonyl compounds with propargylamine to form the imino intermediate, and the involved Au+-complex species with alkynophilicity corresponded to the subsequent activation of imino-tailed alkynyl to afford dehydropyridine intermediate. The latter proceeded auto-oxidation reaction to afford the pyridine derivatives. The observed sequential catalysis over Au-L1 proved more efficient than that over the mechanical mixtures of the Au-complex (Au-L2) and N-methylimidazole, because the free N-methylimidazole as an N-containing donor competed with the alkyne substrate to coordinate to Au-center. Moreover, Au-L1 exhibited good generality to a wide range of the substrates for the synthesis of 2,3-fused pyridine derivatives and 2-aryl(heteroaryl)-substituted pyridines. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2016.09.008

文献信息

• Sequential Amination/Annulation/Aromatization Reaction of Carbonyl Compounds and Propargylamine:  A New One-Pot Approach to Functionalized Pyridines
  作者：Giorgio Abbiati、Antonio Arcadi、Gabriele Bianchi、Sabrina Di Giuseppe、Fabio Marinelli、Elisabetta Rossi

  DOI：10.1021/jo0347260

  日期：2003.9.1

  A general one-pot synthesis of pyridines 4a-t from the reaction of dialkyl acyclic/cyclic ketones 1a-i, methyl, aryl/heteroaryl ketones 1m-r, and aldehydes bearing alpha-hydrogens 1s,t with propargylamine 2 is described. Gold and copper salts are efficient catalysts for the reaction of ketones with 2. The formation of the pyridines 4 is suggested to proceed through the sequential amination of carbonyl

  描述了由二烷基无环/环状酮1a-i，甲基，芳基/杂芳基酮1m-r和带有α-氢1s，t的醛与炔丙基胺2反应的吡啶的一般一锅合成。金盐和铜盐是使酮与2发生反应的有效催化剂。建议通过依次胺化羰基化合物，然后对N-炔丙基亚胺（N-炔丙基二胺）进行区域选择性6-内-挖环化来进行吡啶4的形成。 ）中间体3（5）和芳构化反应。线性多环吡啶4i的制备可以通过使胆甾烷-3-酮1i与2反应来进行，而从胆甾-5-烯-3-酮1j开始已经获得了角型多环吡啶4j。还研究了多环二羰基1k，l与2的反应的选择性。
• Cu-MOF型催化剂在制备多取代吡啶衍生物 中的应用
  申请人：郑州轻工业学院

  公开号：CN107739334B

  公开（公告）日：2020-07-28

  本发明公开了一类Cu‑MOF型催化剂在制备多取代吡啶衍生物中的应用。所述Cu‑MOF型催化剂催化制备多取代吡啶衍生物的方法包括：使包含Cu‑MOF型催化剂、羰基化合物、炔丙基胺和溶剂的均匀混合体系于室温～100℃进行环化反应12～48h，获得多取代吡啶衍生物。本发明初次实现了Cu‑MOF型催化剂催化羰基化合物与炔丙基胺的胺化/环化/芳化反应，高产率地得到了多种多取代的吡啶衍生物；本发明所使用的Cu‑MOF型催化剂为非均相催化剂，对空气和水都很稳定，减少了环境污染，无需惰性气体保护，合成方法简单，原料价格低廉，可以回收并且重复使用；同时，本发明反应温度低、反应选择性高、效率高、底物适用范围广。
• PYRIDINE CGRP RECEPTOR ANTAGONISTS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2846801B1

  公开（公告）日：2017-04-05
• Au-complex containing phosphino and imidazolyl moieties as a bi-functional catalyst for one-pot synthesis of pyridine derivatives
  作者：Da Yang、Huan Liu、Dong-Liang Wang、Yong Lu、Xiao-Li Zhao、Ye Liu

  DOI：10.1016/j.molcata.2016.09.008

  日期：2016.12

  The complex of Au-L1 containing imidazolyl ring and the phosphine-ligated-Au moiety was synthesized and applied as the efficient bi-functional catalyst for the one-pot sequential condensation/annulation reaction for the synthesis of pyridine derivatives. It was found that, as for Au-L1, the involved imidazolyl group acted as a Lewis base to catalyze the condensation of carbonyl compounds with propargylamine to form the imino intermediate, and the involved Au+-complex species with alkynophilicity corresponded to the subsequent activation of imino-tailed alkynyl to afford dehydropyridine intermediate. The latter proceeded auto-oxidation reaction to afford the pyridine derivatives. The observed sequential catalysis over Au-L1 proved more efficient than that over the mechanical mixtures of the Au-complex (Au-L2) and N-methylimidazole, because the free N-methylimidazole as an N-containing donor competed with the alkyne substrate to coordinate to Au-center. Moreover, Au-L1 exhibited good generality to a wide range of the substrates for the synthesis of 2,3-fused pyridine derivatives and 2-aryl(heteroaryl)-substituted pyridines. (C) 2016 Elsevier B.V. All rights reserved.