(R)-2-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoline | 1454914-99-8

• 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: (R)-2-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: (2R)-2-(4-phenylphenyl)-1,2,3,4-tetrahydroquinoline
• CAS: 1454914-99-8
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: GWYGPQGWIFPKJG-OAQYLSRUSA-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

• 作为产物：
  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

文献信息

• A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines
  作者：Erli Sugiono、Magnus Rueping

  DOI：10.3762/bjoc.9.284

  日期：——

  A continuous-flow asymmetric organocatalytic photocyclization–transfer hydrogenation cascade reaction has been developed. The new protocol allows the synthesis of tetrahydroquinolines from readily available 2-aminochalcones using a combination of photochemistry and asymmetric Brønsted acid catalysis. The photocylization and subsequent reduction was performed with catalytic amount of chiral BINOL derived phosphoric acid diester and Hantzsch dihydropyridine as hydrogen source providing the desired products in good yields and with excellent enantioselectivities.

  已开发出一种连续流动的不对称有机催化光环化-转移氢化串联反应。新的方案允许利用光化学和不对称的Brønsted酸催化合成四氢喹啉，从易得的2-氨基茜素开始。光环化和随后的还原是通过催化量的手性BINOL衍生磷酸二酯和Hantzsch二氢吡啶作为氢源进行的，以良好的产率和优异的对映选择性提供所需的产物。
• B(C₆F₅)₃-Promoted hydrogenations of N-heterocycles with ammonia borane
  作者：Fangwei Ding、Yiliang Zhang、Rong Zhao、Yanqiu Jiang、Robert Li-Yuan Bao、Kaifeng Lin、Lei Shi

  DOI：10.1039/c7cc04709f

  日期：——

  A transition-metal-free method for the B(C6F5)3-promoted hydrogenations of N-heterocycles using ammonia borane under mild reaction conditions has been developed. The reaction affords a broad range of hydrogenated products in moderate to good yields. The enantioselective versions for the corresponding products were also investigated via our approach, showing good feasibility.

  已开发出一种无过渡金属的方法，该方法使用硼烷氨在温和的反应条件下进行B（C 6 F 5）3促进的N-杂环加氢反应。该反应以中等至良好的产率提供了广泛的氢化产物。还通过我们的方法对相应产品的对映选择性进行了研究，显示出良好的可行性。
• 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。
• Hyper-Crosslinked Porous Chiral Phosphoric Acids: Robust Solid Organocatalysts for Asymmetric Dearomatization Reactions
  作者：Xian-Yun Huang、Qingshu Zheng、Lei-Ming Zou、Qing Gu、Tao Tu、Shu-Li You

  DOI：10.1021/acscatal.2c00397

  日期：2022.4.15

  an effective strategy for the synthesis of porous polymers in recent years. Here, we report the synthesis of porous chiral phosphoric acids by this strategy. Moreover, these porous chiral phosphoric acids were found to enable highly enantioselective dearomatization reactions. Remarkably, after being reused for 10 runs, no obvious loss in catalytic activity and selectivity was observed. The features of

  近年来，使用外部交联剂编织刚性芳烃结构单元已发展成为合成多孔聚合物的有效策略。在这里，我们报告了通过这种策略合成多孔手性磷酸。此外，发现这些多孔手性磷酸能够实现高度对映选择性的脱芳构化反应。值得注意的是，在重复使用 10 次后，没有观察到催化活性和选择性的明显损失。这些超交联多孔手性磷酸的高反应性、选择性、稳定性和可回收性等特点对实际催化剂设计具有重要意义。
• Enantioselective Synthesis of Tetrahydroquinolines by Borrowing Hydrogen Methodology: Cooperative Catalysis by an Achiral Iridacycle and a Chiral Phosphoric Acid
  作者：Ching Si Lim、Thanh Truong Quach、Yu Zhao

  DOI：10.1002/anie.201703704

  日期：2017.6.12

  We report herein the highly enantioselective synthesis of 2‐substituted tetrahydroquinolines through borrowing hydrogen, a process recognized for its environmentally benign and atom‐economical nature. The use of an achiral iridacycle complex in combination with a chiral phosphoric acid as catalysts was the key to the development of this highly efficient and enantioselective transformation.

  我们在这里报告了通过借用氢对2-取代的四氢喹啉的高度对映选择性的合成方法，该方法因其对环境的友好性和原子经济性而得到认可。非手性iridacycle配合物与手性磷酸的组合使用作为催化剂是开发这种高效和对映选择性转化的关键。