1-benzyl-2,6,7,8-tetrahydro-2,2-dimethylquinolin-5(1H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-2,6,7,8-tetrahydro-2,2-dimethylquinolin-5(1H)-one
• 英文别名: 1-Benzyl-2,6,7,8-tetrahydro-2,2-dimethylquinolin-5(1h)-one；1-benzyl-2,2-dimethyl-7,8-dihydro-6H-quinolin-5-one
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: FZWNQQCNAQCOLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄胺 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 1-benzyl-2,6,7,8-tetrahydro-2,2-dimethylquinolin-5(1H)-one
  参考文献：
  名称：

  Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition

  摘要：

  A simple and efficient method to synthesize a variety of tetrahydroquinolinones was successfully achieved by reacting various beta-enaminones with several alpha,beta-unsaturated aldehydes. This strategy can be viewed as a Bronsted acid-mediated formal [3+3] cycloaddition.

  DOI：

  10.1007/s00706-012-0762-0

文献信息

• Stereodivergent Approach to Both C2,8a-syn and C2,8a-anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCl4-Promoted Aza-[3+3] Annulation
  作者：Richard Hsung、Gang Li、Lauren Carlson、Irina Sagamanova、Brian Slafer、Claudio Gilardi、Heather Sklenicka、Nadiya Sydorenko

  DOI：10.1055/s-0029-1216920

  日期：2009.9

  Details in developing a stereodivergent approach to the lepadin family and establishing an entry to both C2,8a-syn and C2,8a-anti relative stereochemical manifolds through a common intermediate are described here. This works paves the foundation for constructing all members of the lepadin family, which consists of three subsets based on an array of interesting relative configurations. These efforts underline the prominence of aza-[3+3] annulation as a unified strategy in alkaloid synthesis.

  本文详细描述了开发立体选择性方法合成lepadin家族化合物，并通过一个共同中间体建立了C2,8a-syn和C2,8a-anti相对立体化学空间的入口。这项工作为构建基于一系列有趣相对构型的三个亚组的lepadin家族所有成员奠定了基础。这些努力突显了氮杂-[3+3]环化作为生物碱合成统一策略的重要性。
• Formal Cycloaddition Reactions of Vinylogous Amides with α,β-Unsaturated Iminiums. A Strategy for Constructing Piperidinyl Heterocycles
  作者：Richard P. Hsung、Lin-Li Wei、Heather M. Sklenicka、Christopher J. Douglas、Michael J. McLaughlin、Jason A. Mulder、Letitia J. Yao

  DOI：10.1021/ol990107v

  日期：1999.8.1

  A formal [3 + 3] cycloaddition strategy for constructing piperidinyl heterocycles from vinylogous amides and alpha,beta-unsaturated iminiums is described here, These reactions proceed well, leading to various heterocycles that could serve as useful synthetic building blocks. Comparative studies between the reactivities of vinylogous amides and other 1,3-diketo systems have also been examined. Preferences for the nitrogen atom during the electrocyclic ring closure step are noted in these reactions, and preliminary calculations suggest that these preferences could result from electronic factors.
• Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition
  作者：Quang Huy To、Yong Rok Lee、Sung Hong Kim

  DOI：10.1007/s00706-012-0762-0

  日期：2012.10

  A simple and efficient method to synthesize a variety of tetrahydroquinolinones was successfully achieved by reacting various beta-enaminones with several alpha,beta-unsaturated aldehydes. This strategy can be viewed as a Bronsted acid-mediated formal [3+3] cycloaddition.