2,4-diphenyl-1,2,3,4-tetrahydroquinoline

• 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: 2,4-diphenyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (2S,4R)-2,4-diphenyl-1,2,3,4-tetrahydroquinoline
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: UJXHLFHOXNRSGT-CTNGQTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：

  2,4-diphenyl-3,4-dihydroquinoline 在 三乙酰氧基硼氢化钠 作用下， 以 水 、 甲苯 为溶剂， 以63 mg的产率得到2,4-diphenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines

  摘要：

  Rh催化的2-氨基苯硼酸衍生物的共轭加成被用于四氢喹啉的对映选择性和不对称合成。

  DOI：

  10.1039/c4cc04940c

文献信息

• Enantioselective Metal-Free Hydrogenations of Disubstituted Quinolines
  作者：Zhenhua Zhang、Haifeng Du

  DOI：10.1021/acs.orglett.5b03307

  日期：2015.12.18

  A metal-free hydrogenation of 2,4-disubstituted quinolines was realized for the first time using chiral diene derived borane catalysts to furnish the corresponding tetrahydroquinolines in 75–98% yields with 95/5−99/1 dr’s and 86–98% ee’s. This catalytic system was also effective for 2,3-disubstituted quinolines to give moderate to good ee’s.

  首次使用手性二烯衍生的硼烷催化剂实现了2,4-二取代喹啉的无金属氢化，以75–98％的产率提供了95 / 5–99 / 1 dr's和86–98％ee的相应四氢喹啉。 。该催化体系对于2，3-二取代的喹啉也同样有效，以产生中等至良好的ee。
• From Nitrobenzenes to Substituted Tetrahydroquinolines in a Single Step by a Domino Reduction/Imine Formation/Aza-Diels–Alder Reaction
  作者：Hans-Georg Imrich、Jürgen Conrad、Denis Bubrin、Uwe Beifuss

  DOI：10.1021/jo502882y

  日期：2015.2.20

  The three-component reaction between a nitrobenzene, an aldehyde, and a dienophile in the presence of iron powder as a reductant and montmorillonite K10 as a catalyst in aqueous citric acid delivers the products of an aza-Diels–Alder (Povarov) reaction with high endo-selectivity and yields up to 99%.

  柠檬酸水溶液中，在铁粉作为还原剂和蒙脱土K10作为催化剂的存在下，硝基苯，醛和亲二烯体之间的三组分反应可提供高氮杂-Diels-Alder（Povarov）反应的产物内选择性，产率高达99％。
• Mechanochemical milling promoted solvent-free imino Diels–Alder reaction catalyzed by FeCl₃: diastereoselective synthesis of cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines
  作者：Ya-Jun Tan、Ze Zhang、Fang-Jian Wang、Hao-Hao Wu、Qing-Hai Li

  DOI：10.1039/c4ra05252h

  日期：——

  Cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines were diastereoselectively synthesized by FeCl₃-promoted solvent-free Diels–Alder reaction of in situ generated imine with styrene under ball milling.

  通过FeCl3促进的无溶剂Diels–Alder反应，在球磨条件下，利用现场生成的亚胺与苯乙烯，对Cis-2,4-二苯基-1,2,3,4-四氢喹啉进行了对映选择性合成。
• A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines
  作者：Ho Yin Li、Joachim Horn、Amanda Campbell、David House、Adam Nelson、Stephen P. Marsden

  DOI：10.1039/c4cc04940c

  日期：——

  Rh-catalysed conjugate additions of 2-aminophenyl boronic acid derivatives were exploited in diastereoselective and asymmetric syntheses of tetrahydroquinolines.

  Rh催化的2-氨基苯硼酸衍生物的共轭加成被用于四氢喹啉的对映选择性和不对称合成。
• Photosensitized Diels–Alder reactions of N-arylimines: synthesis of tetrahydroquinoline derivatives
  作者：Wei Zhang、Xiaodong Jia、Li Yang、Zhong-Li Liu

  DOI：10.1016/s0040-4039(02)02328-6

  日期：2002.12

  Irradiation (lambda>345 nm) of catalytic amounts of 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) in a CH2Cl2 solution of N-aryl imines and alpha-methyl styrene or styrene produced the corresponding [4+2] cycloaddition products, tetrahydroquinoline derivatives, in good yield. The reaction was controlled by the relative oxidation potentials of the dienophile and the diene. (C) 2002 Elsevier Science Ltd. All rights reserved.