trans-1,3-dimethyl-4-phenyl-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: trans-1,3-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (3S,4R)-1,3-dimethyl-4-phenyl-3,4-dihydro-2H-quinoline
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: GIFNDCZFKWTDLQ-CXAGYDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲基苯乙烯 、 <(Methylphenylamino)methyl>phenylsulfid 在 四氯化钛 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到trans-1,3-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Intermolecular polar [4π⁺+ 2π] cycloadditions of cationic 2-azabutadienes from thiomethylamines: a new and efficient method for the regio- and diastereo-selective synthesis of 1,2,3,4-tetrahydroquinolines

  摘要：

  通过分子间极性[4Ï++ 2Ï]环加成反应，从硫代甲基胺和各种二烯烃中生成阳离子 2-氮杂丁二烯，从而高度区域和非对映选择性地形成了取代的 1,2,3,4-四氢喹啉和相关缩合氮杂环，收率从 57% 到 100% 不等。

  DOI：

  10.1039/c39950002137

文献信息

• Lewis acid assisted reactions of<i>N</i>-(α- aminoalkyl)benzotriazoles and unactivated alkenes for the facile synthesis of 4-, 2,4-, and 3,4-substituted 1,2,3,4-tetrahydroquinolines
  作者：Alan R. Katritzky、Daniel A. Nichols、Ming Qi、Baozhen Yang

  DOI：10.1002/jhet.5570340428

  日期：1997.7

  A range of substituted tetrahydroquinolines have been synthesized from benzotriazole derivatives and unactivated alkenes in the presence of a Lewis acid. These reactions utilize readily available starting materials and mild reaction conditions, and give high yields. The reaction mechanisms are discussed.

  在路易斯酸的存在下，由苯并三唑衍生物和未活化的烯烃合成了一系列取代的四氢喹啉。这些反应利用容易获得的原料和温和的反应条件，并获得高收率。讨论了反应机理。
• Practical One‐Pot Procedure for the Synthesis of 1,2,3,4‐Tetrahydroquinolines by the Imino‐Diels‐Alder Reaction
  作者：Christoph M. Dehnhardt、Yomery Espinal、Aranapkam M. Venkatesan

  DOI：10.1080/00397910701820988

  日期：2008.2.13

  Abstract A novel‐one‐pot procedure for the synthesis of tetrahydroquinolines via the imino‐Diels‐Alder reaction is described. This procedure gives better yields and exhibits better versatility for alkene substrates than the existing hemi‐aminal based methodologies.

  摘要 描述了一种通过亚氨基-狄尔斯-阿尔德反应合成四氢喹啉的新型单锅法。与现有的基于半胺的方法相比，该方法对烯烃底物具有更好的收率和更好的多功能性。
• Asymmetric Syntheses of 3,4-Substituted Tetrahydroquinoline Derivatives by (-)-Sparteine-Mediated Dynamic Thermodynamic Resolution of 2-(α-Lithiobenzyl)-<i>N</i>-pivaloylaniline
  作者：Yong Park、Yongtae Kim、Eun-kyoung Shin、Peter Beak

  DOI：10.1055/s-2006-950299

  日期：2006.11

  (-)-Sparteine-mediated dynamic thermodynamic resolution of 2-(α-lithiobenzyl)-N-pivaloylaniline was investigated. A temperature- and concentration-controlled epimerization-substitution sequence provides a simple protocol for the preparation of a highly enantioenriched benzyl-substituted N-pivaloylaniline product (up to 98:2 er). Also, application of this simple methodology to asymmetric syntheses of 1,3,4- and 3,4-substituted tetrahydroquinoline derivatives is demonstrated.

  研究了 (-)-Sparteine 介导的 2-(δ-硫代苄基)-N-新戊酰基苯胺的动态热力学解析。温度和浓度受控的外嵌合-取代序列为制备高对映体富集的苄基取代 N-新戊酰基苯胺产品（高达 98:2 er）提供了一个简单的方案。此外，还展示了这一简单方法在 1,3,4- 和 3,4- 取代的四氢喹啉衍生物的不对称合成中的应用。
• A Versatile Method for the Preparation of Substituted 1,2,3,4-Tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00128a041

  日期：1995.11

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 1 react with acetaldehyde to give 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 11 in good yields along with minor amounts of diamines 12. Reactions of 1 with higher enolizable aldehydes R(1)CH(2)CHO lead to 4-(benzotriazol-1-yl)tetrahydroquinolines with an R(1) substituent at C-3 (17, 18). Condensation of N-methylaniline with two molecules of aldehyde RCH(2)CHO and one molecule of benzotriazole produces 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 34 bearing an R substituent at C-3 and RCH(2) on C-2. In all of these products, the benzotriazol-1-yl moiety can be replaced by a hydrogen atom (by reduction with lithium aluminum hydride) or by an alkyl or aryl group (by reaction with a Grignard reagent). Treatment of 11 with sodium alkoxides leads to 4-alkoxy-1,2,3,4-tetrahydroquinolines 10. Elimination of a molecule of nitrogen from the benzotriazole system of 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 17, 18, and 35 by sodium hydride produces the corresponding 4-(phenylamino)-1,2-dihydroquinolines 26 (R(1) = alkyl) or 4-(phenylimino)-1,2,3,4-tetrahydroquinolines 27 and 38 (R = Ph), depending on the nature of the substituents at C-3 and the workup conditions.
• Intermolecular polar [4π⁺+ 2π] cycloadditions of cationic 2-azabutadienes from thiomethylamines: a new and efficient method for the regio- and diastereo-selective synthesis of 1,2,3,4-tetrahydroquinolines
  作者：Uwe Beifuss、Sabine Ledderhose

  DOI：10.1039/c39950002137

  日期：——

  Substituted 1,2,3,4-tetrahydioquinolines and related condensed nitrogen-heterocycles are formed highly regio- and diastereo-selectively with yields ranging from 57 to 100% by intermolecular polar [4π++ 2π] cycloadditions of cationic 2-azabutadienes from thiomethylamines and various dienophiles.

  通过分子间极性[4Ï++ 2Ï]环加成反应，从硫代甲基胺和各种二烯烃中生成阳离子 2-氮杂丁二烯，从而高度区域和非对映选择性地形成了取代的 1,2,3,4-四氢喹啉和相关缩合氮杂环，收率从 57% 到 100% 不等。