trans-3,4-epoxy-2-methyl-1-toluoyl-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-3,4-epoxy-2-methyl-1-toluoyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 3,4-epoxy-2-methyl-1-(p-toluoyl)-1,2,3,4-tetrahydroquinoline；[(1aS,2S,7bR)-2-methyl-2,7b-dihydro-1aH-oxireno[2,3-c]quinolin-3-yl]-(4-methylphenyl)methanone
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: VQSRXJUFVIFUHB-AFAVFJNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-3,4-epoxy-2-methyl-1-toluoyl-1,2,3,4-tetrahydroquinoline 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以67%的产率得到4-chloro-2-methyl-1-p-toluoyl-1,2,3,4-tetrahydroquinolin-3-ol
  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 在 TEA 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 trans-3,4-epoxy-2-methyl-1-toluoyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Synthesis and in Vitro Multidrug Resistance Modulating Activity of a Series of Dihydrobenzopyrans and Tetrahydroquinolines

  摘要：

  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.

  DOI：

  10.1021/jm980517+

文献信息

• Synthesis of [1,4]dioxino[2,3-<i>c</i>]quinolines and [1,4]dioxepino-[2,3-<i>c</i>]quinolines and their 1-sulfur analogues
  作者：Romana Hiessböck、Martin Kratzel

  DOI：10.1002/jhet.5570360530

  日期：1999.9

  The synthesis of [1,4]dioxino[2,3-c]quinolines and [1,4]dioxepino[2,3-c]quinolines with restrained conformation of the piperidine ring, which represent 1,2,3,4-tetrahydroquinolines containing two heteroatom substituents at positions 3 and 4, is described. In addition, the application of this approach for the synthesis of 1-sulfur analogues is discussed. Both series are helpful tools for three-dimensional

  的[1,4]二氧杂环己二烯并[2,3-合成Ç ]喹啉和[1,4]恶庚因并[2,3- c ^〕喹啉与哌啶环的构象约束，其代表1,2,3,4-描述了在位置3和4处包含两个杂原子取代基的四氢​​喹啉。另外，讨论了该方法在合成1-硫类似物中的应用。这两个系列都是在多药耐药性调节剂领域进行三维定量构效关系研究的有用工具。
• Hiessboeck; Huber; Kratzel, Scientia Pharmaceutica, 1996, vol. 64, # 3-4, p. 445 - 454
  作者：Hiessboeck、Huber、Kratzel

  DOI：——

  日期：——
• 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.
• Synthesis and stereochemistry of 1-acyl-2-alkyl-1,2,3,4-tetrahydroquinoline-3,4-epoxides
  作者：M. Kratzel、R. Hiessb�ck、H. V�llenkle

  DOI：10.1007/bf00812711

  日期：——

  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.
• 2-Alkyl- and 2-Cyano-substituted 1-Acyl-3,4-epoxy-1,2,3,4-tetrahydroquinolines --- Reactions with O-Nucleophiles
  作者：Martin Kratzel、Romana Hiessböck

  DOI：10.3987/com-95-7380

  日期：——