2-methyl-1-(p-toluoyl)-1,2-dihydroquinoline | 159721-62-7

• 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
• 英文名称: 2-methyl-1-(p-toluoyl)-1,2-dihydroquinoline
• 英文别名: (4-methylphenyl)-(2-methyl-2H-quinolin-1-yl)methanone
• CAS: 159721-62-7
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: ZTCBKNYDXOBENQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-1-(p-toluoyl)-1,2-dihydroquinoline 在 吡啶 、 氢氧化钾 、 ammonium cerium(IV) nitrate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.5h， 生成 (2SR,3RS,4SR)-3,4-epoxy-2-methyl-1-p-toluoyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Diastereoselective Synthesis of 2-Alkyl-1,2,3,4-tetrahydroquinolin-3-ols — An Example of Diastereoconversion of a-Alkyl Epoxides

  摘要：

  The efficient synthesis of both diastereomers of 2-alkyl-1,2,3,4-tetrahydroquinolin-3-ols, representing rigid 1,2-amino alcohols, is outlined applying a diastereoconversion approach. The relative configuration of the title compounds is supported by the unequivocal stereochemical course of the reactions used.

  DOI：

  10.3987/com-99-s96
• 作为产物：
  描述：

  2-methyl-1,2-dihydroquinoline 、 对甲基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到2-methyl-1-(p-toluoyl)-1,2-dihydroquinoline
  参考文献：
  名称：

  Synthesis and stereochemistry of 1-acyl-2-alkyl-1,2,3,4-tetrahydroquinoline-3,4-epoxides

  摘要：

  Analogous to the recently described synthesis of Reissert epoxides the treatment of 1-acyl-2-alkyl-1,2-dihydroquinolines with m-chloroperoxybenzoic acid gave diasteromeric pure epoxides which are stable in crystalline state, but reactive in solution versus nucleophiles. Acting as useful intermediates to stereocontrolled functionalized 1,2,3,4-tetrahydroquinolines an X-ray analysis was performed to confirm the relative stereochemistry of the epoxides.

  DOI：

  10.1007/bf00812711

文献信息

• Synthesis and in Vitro Multidrug Resistance Modulating Activity of a Series of Dihydrobenzopyrans and Tetrahydroquinolines
  作者：Romana Hiessböck、Christian Wolf、Elisabeth Richter、Manuela Hitzler、Peter Chiba、Martin Kratzel、Gerhard Ecker

  DOI：10.1021/jm980517+

  日期：1999.6.1

  A series of dihydrobenzopyrans and tetrahydroquinolines was synthesized and pharmacologically tested for their ability to inhibit P-glycoprotein mediated daunomycin efflux in multidrug resistant CCRF-CEM vcr1000 cells. Several compounds exhibit activities in the range of the reference compounds verapamil and propafenone. Preliminary structure-activity relationship studies propose the importance of high molar refractivity values of the compounds and the presence of an additional basic nitrogen atom.
• 1-Acyl-2-alkyl-3,4-epoxy-1,2,3,4-tetrahydroquinolines — Synthesis and Reactions with N-Nucleophiles
  作者：Martin Kratzel、Romana Hiessböck

  DOI：10.3987/com-94-6677

  日期：——

  Epoxide opening of the title compounds (6) with primary or secondary amines using lithium perchlorate as catalyst gave 1,2,3,4-tetrahydroquinolines with stereochemically well defined substitution pattern in the piperidine moiety (7,8). By-products (9,10), formed by acyl migration, were observed.
• Kratzel M., Hiessboeck R., Voellenkle H., Monatsh. Chem., 125 (1994) N 8-9, S 963-967
  作者：Kratzel M., Hiessboeck R., Voellenkle H.

  DOI：——

  日期：——