2-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoline | 1454914-88-5

• 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-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-(Biphenyl-4-yl)-1,2,3,4-tetrahydroquinoline；2-(4-phenylphenyl)-1,2,3,4-tetrahydroquinoline
• CAS: 1454914-88-5
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: GWYGPQGWIFPKJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoline 在 盐酸 、 (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 、 bis(2,6-dichlorobenzyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 、 N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate 作用下， 以 正己烷 、 水 、 甲苯 为溶剂， 反应 60.0h， 以95%的产率得到(R)-2-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Single-Operation Deracemization of 3H-Indolines and Tetrahydroquinolines Enabled by Phase Separation

  摘要：

  The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

  DOI：

  10.1021/ja4082827
• 作为产物：
  描述：

  2-氯喹啉 在 四(三苯基膦)钯 、 sodium cyanoborohydride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 反应 48.0h， 生成 2-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

  摘要：

  四氢喹啉与酮亚胺在手性磷酸存在下的标题反应以高效转化和优异对映选择性进行。

  DOI：

  10.1039/c5cc06436h

文献信息

• Asymmetric Synthesis of Hydroquinolines with α,α‐Disubstitution through Organocatalyzed Kinetic Resolution
  作者：Yunrong Chen、Chaofan Zhu、Zheng Guo、Wei Liu、Xiaoyu Yang

  DOI：10.1002/anie.202015008

  日期：2021.3

  The first kinetic resolution of hydroquinoline derivatives with α,α‐disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate‐ and enantio‐determining electrophilic attack promoted by a network of attractive non‐covalent interactions between

  通过手性磷酸催化偶氮二羧酸酯的不对称远程胺化，实现了具有α，α-二取代的氢喹啉衍生物的第一动力学拆分。机理研究表明，单体催化剂途径通过确定底物和催化剂之间有吸引力的非共价相互作用网络促进速率和对映体确定亲电性进攻。新引入的肼部分的后续轻松移除和转化使这些方案成为强大的工具，可用于不对称合成具有α，α-取代基的N-杂环。
• Organocatalytic Approach for Transfer Hydrogenation of Quinolines, Benzoxazines and Benzothiazines
  作者：Xiang Qiao、Zongbi Bao、Huabin Xing、Yiwen Yang、Qilong Ren、Zhiguo Zhang

  DOI：10.1007/s10562-017-2061-1

  日期：2017.7

  AbstractThis study reports on the thiourea dioxide catalyzed transfer hydrogenation of diverse C=N–containing heterocyclic compounds with Hantzsch ester as the hydrogen source. With this cost effective and readily available catalyst, a wide range of 2-substituted quinolines, 3-substituted-2H-1,4-benzoxazines and 3-substituted-2H-1,4-benzothiazines were efficiently reduced to the corresponding tetrahydroquinolines

  摘要 本研究报道了二氧化硫脲催化多种含 C=N 杂环化合物以 Hantzsch 酯为氢源的转移氢化。使用这种具有成本效益且易于获得的催化剂，广泛的 2-取代喹啉、3-取代-2H-1,4-苯并恶嗪和 3-取代-2H-1,4-苯并噻嗪被有效地还原为相应的四氢喹啉、二氢-2H-苯并恶嗪和二氢-2H-苯并噻嗪在温和条件下。图形摘要本研究报告了二氧化硫脲催化的 2-取代喹啉、3-取代-2H-1,4-苯并恶嗪和 3-取代-2H-以 Hantzsch 1,4-二氢吡啶为氢源的 1,4-苯并噻嗪。
• Cyclopentadiene-based Brønsted acid as a new generation of organocatalyst for transfer hydrogenation of 2-substituted quinoline derivatives
  作者：Xiang Qiao、Mahmoud El-Shahat、Bakhtar Ullah、Zongbi Bao、Huabin Xing、Li Xiao、Qilong Ren、Zhiguo Zhang

  DOI：10.1016/j.tetlet.2017.04.038

  日期：2017.5

  A simple and readily available cyclopentadiene-based Brønsted acid was employed to catalyze the transfer hydrogenation of 2-substituted quinolines using Hantzsch ester as the hydrogen source. This conceptually new designed organocatalyst demonstrates remarkably high efficiency for this transformation and a variety of substituted 1,2,3,4-tetrahydroquinoline derivatives were afforded in excellent yields

  使用Hantzsch酯作为氢源，使用一种简单易用的基于环戊二烯的布朗斯台德酸催化2-取代的喹啉的转移加氢反应。这种概念上新颖设计的有机催化剂证明了这种转化的高效性，并且在温和的反应条件下，以优异的收率提供了各种取代的1,2,3,4-四氢喹啉衍生物。
• Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Brønsted Acid
  作者：Raja Mitra、Hui Zhu、Stefan Grimme、Jochen Niemeyer

  DOI：10.1002/anie.201704647

  日期：2017.9.11

  Interlocked molecules, such as catenanes, rotaxanes, and molecular knots, have become interesting candidates for the development of sophisticated chemical catalysts. Herein, we report the first application of a catenane-based catalyst in asymmetric organocatalysis, revealing that the catenated catalyst shows dramatically increased stereoselectivities (up to 98 % ee) in comparison to its non-interlocked

  连锁分子，例如链烷，轮烷和分子链结，已成为开发复杂化学催化剂的有趣候选物。在此，我们报道了基于链烷烃的催化剂在不对称有机催化中的首次应用，揭示了与非链状类似物相比，链状催化剂显示出极大的立体选择性（高达98％ee）。通过DFT研究得出了观察到的差异的机械原理，表明立体确定反应步骤中两个催化活性基团的参与是联锁催化剂优越的选择性的原因。
• S-Benzyl-N,N'-diphenyl substituted isothiouronium iodide as a highly efficient organocatalyst for transfer hydrogenation of 2-substituted quinolines
  作者：Sungmin Kang、Taek Hyeon Kim

  DOI：10.1016/j.tetlet.2021.153450

  日期：2021.11

  prepared from thiourea was first employed to catalyze the transfer hydrogenation of various 2-alkyl and arylquinolines with Hantzsch ester as the hydrogen source. This metal-free catalyzed reduction of 2-substituted quinoline efficiently rendered good to excellent yields of tetrahydroquinolines under mild conditions with a small amount of catalyst (5 mol%).

  由硫脲制备的异硫脲有机催化剂首先用于以汉茨酯为氢源催化各种 2-烷基和芳基喹啉的转移氢化。这种无金属催化的 2-取代喹啉还原反应在温和条件下使用少量催化剂 (5 mol%) 有效地提高了四氢喹啉的产率。