1-p-toluoyl-1,2-dihydro-quinoline-2-carbonitrile | 70391-32-1

• 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: 1-p-toluoyl-1,2-dihydro-quinoline-2-carbonitrile
• 英文别名: 1-p-Toluoyl-1,2-dihydro-chinolin-2-carbonitril；1-(4-methylbenzoyl)-2H-quinoline-2-carbonitrile
• CAS: 70391-32-1
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: XDWWHAZSPYDPLI-UHFFFAOYSA-N

物化性质

• 沸点：
  501.4±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-p-toluoyl-1,2-dihydro-quinoline-2-carbonitrile 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(2RS,3SR,4RS)-2-cyano-3,4-epoxy-1-(4-methylbenzoyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Reissert epoxides: Novel oxidation products of quinoline reissert compounds

  摘要：

  Treatment of quinoline Reissert compounds with m-chloroperoxybenzoic acid gave epoxides which are remarkably stable in crystalline state, but reactive in solution versus nucleophiles. They represent useful intermediates to regioselectively functionalized quinolines.

  DOI：

  10.1007/bf00810030
• 作为产物：
  描述：

  喹啉 、 对氯甲苯 、 氰化钾 在 水 作用下， 生成 1-p-toluoyl-1,2-dihydro-quinoline-2-carbonitrile
  参考文献：
  名称：

  The Rearrangement and Condensation of Reissert Compounds with Grignard Reagents¹

  摘要：

  DOI：

  10.1021/ja01585a043

文献信息

• Regioselective Introduction of Homoallylic Amine Moiety to Quinolines: Preparation of Reissert Compound Followed by In-Mediated Allylation of Nitrile
  作者：Sung-Hwan Kim、Sang-Ku Lee、Yu-Mi Kim、Jae-Nyoung Kim

  DOI：10.5012/bkcs.2010.31.12.3822

  日期：2010.12.20
• Reissert epoxides: Novel oxidation products of quinoline reissert compounds
  作者：Martin Kratzel、Romana Hiessböck

  DOI：10.1007/bf00810030

  日期：1993.11

  Treatment of quinoline Reissert compounds with m-chloroperoxybenzoic acid gave epoxides which are remarkably stable in crystalline state, but reactive in solution versus nucleophiles. They represent useful intermediates to regioselectively functionalized quinolines.
• KAMATH H. V.; NARGUND K. S.; KULKARNI S. N., INDIAN J. CHEM., 1978, B 16, 903-906
  作者：KAMATH H. V.、 NARGUND K. S.、 KULKARNI S. N.

  DOI：——

  日期：——
• REISSERT COMPOUNDS AS ANTI-HIV AGENTS
  申请人：THE UPJOHN COMPANY

  公开号：EP0579695A1

  公开（公告）日：1994-01-26
• [EN] REISSERT COMPOUNDS AS ANTI-HIV AGENTS
  申请人：THE UPJOHN COMPANY

  公开号：WO1992016508A1

  公开（公告）日：1992-10-01

  (EN) Disclosed are heterocyclic compounds of formula (I). The compounds of the invention are useful in the treatment of AIDS and AIDS related complex. The compounds of the invention are generally synthesized by following the reactions and conditions used to make Reissert compounds. Compounds included within the scope of formula (I) are 1,2-dihydroquinolines, 1,4-dihydroquinolines, 1,2,3,4-tetrahydroquinolines, 1,2-dihydroquinazolines, and the 1,2-dihydroquinoxalines. Representative compounds include 1-(4-bromobenzoyl)-2-cyano-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-5-fluoro-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-6-fluoro-1,4-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,2,3,4-tetrahydroquinoline, 1-(4-chlorobenzoyl)-2-carboximidamide-8-fluoro-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,4-dihydroquinoxaline, 1-E-(3-(4-chlorophenyl)-1-oxo-2-propenyl)-2-cyano-1,2-dihydroquinoline, and 1-E-(3-(4-chlorophenyl)-1-oxo-2-propenyl)-2-carboximidamide-1,2-dihydroquinoline. Also included within the scope of the invention is a method of treating a human having AIDS or ARC with an effective amount of a compound of the invention.(FR) L'invention se rapporte à des composés hétérocycliques représentés par la formule (I), qui servent au traitement du sida et du syndrome associé au sida. Ces composés sont généralement synthétisés en suivant les réactions et les conditions utilisées pour produire les composés Reissert. Les composés de la formule (I) sont les 1,2-dihydroquinolines, les 1,4-dihydroquinolines, les 1,2,3,4-tétrahydroquinolines, les 1,2-dihydroquinazolines et les 1,2-dihydroquinoxalines. Les composés types sont 1-(4-bromobenzoyl)-2-cyano-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-5-fluoro-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-6-fluoro-1,4-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,2,3,4-tétrahydroquinoline, 1-(4-chlorobenzoyl)-2-carboximidamide-8-fluoro-1,2-dihydroxyquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,4-dihydroquinoxaline, 1-E-(3-(4-chlorophényl)-1-oxo-2-propényl)-2-cyano-1,2-dihydroquinoline et 1-E-(3-(4-chlorophényl)-1-oxo-2-propényl)-2-carboximidamide-1,2-dihydroquinoline. L'invention décrit également un procédé de traitement du sida ou du syndrome associé au sida grâce à une quantité efficace d'un de ces composés.