N-(2-bromo-2-methylpropanoyl)-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: N-(2-bromo-2-methylpropanoyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-(2-Bromo-2-methylpropanoyl)-1,2,3,4-tetrahydroquinoline；2-bromo-1-(3,4-dihydro-2H-quinolin-1-yl)-2-methylpropan-1-one
• 化学式: C₁₃H₁₆BrNO
• 分子量: 282.18
• InChiKey: AAJXPPABGJWGIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  N-(2-bromo-2-methylpropanoyl)-1,2,3,4-tetrahydroquinoline 在 potassium phosphate 、 四(三苯基膦)镍 、 1,3-双(二苯基膦)丙烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以72%的产率得到5,6-dihydro-1,1-dimethyl-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one
  参考文献：
  名称：

  Nickel-Catalyzed Aromatic C–H Alkylation with Secondary or Tertiary Alkyl–Bromine Bonds for the Construction of Indolones

  摘要：

  A nickel-catalyzed aromatic C-H alkylation with tertiary or secondary alkyl-Br bonds for the construction of indolones was demonstrated. Various functional groups were well tolerated. Moreover, the challenging secondary alkyl bromides were well introduced in this transformation. Radical trapping and photocatalysis conditions exhibited that it is most likely to be a radical process for this aromatic C-H alkylation.

  DOI：

  10.1021/ol403021p

文献信息

• Photochemical Reactions of N-(2-Halogenoalkanoyl) Derivatives of Anilines
  作者：Takehiko Nishio、Hidenori Asai、Takenori Miyazaki

  DOI：10.1002/1522-2675(20000705)83:7<1475::aid-hlca1475>3.0.co;2-y

  日期：2000.7.5

  The photochemical reactions of 2-substituted N-(2-halogenoalkanoyl) derivatives 1 of anilines and 5 of cyclic amines are described. Under irradiation, 2-bromo-2-methylpropananilides 1a – e undergo exclusively dehydrobromination to give N-aryl-2-methylprop-2-enamides (=methacrylanilides) 3a – e (Scheme 1 and Table 1). On irradiation of N-alkyl- and N-phenyl-substituted 2-bromo-2-methylpropananilides

  描述了苯胺的 2-取代的 N-(2-卤代烷酰基) 衍生物 1 和环胺的 5 的光化学反应。在辐照下，2-溴-2-甲基丙酰苯胺 1a – e 仅进行脱溴氢反应，得到 N-芳基-2-甲基丙酰苯胺（=甲基丙烯酰苯胺）3a – e（方案 1 和表 1）。在辐照 N-烷基和 N-苯基取代的 2-溴-2-甲基丙苯胺 1f – m 时，环化产物，即 1,3-二氢-2H-吲哚-2-酮 (=oxindoles) 2f – m 和 3 ,4-二氢喹啉-2(1H)-ones (=dihydrocarbostyrils) 4f – m, 除了 3f – m。另一方面，N-甲基取代的 2-氯-2-苯基乙酰苯胺 1o - q 和 2-氯乙酰苯胺 1r 的辐照产生了羟吲哚 2o - r 作为唯一的产物，但收率低（方案 3 和表 2）。相应的 N-苯基衍生物 1s - v 光环化为羟吲哚 2s - v 进行顺利。提出了形成光产物的合理机制（方案
• Nickel-Catalyzed Aromatic C–H Alkylation with Secondary or Tertiary Alkyl–Bromine Bonds for the Construction of Indolones
  作者：Chao Liu、Dong Liu、Wei Zhang、Liangliang Zhou、Aiwen Lei

  DOI：10.1021/ol403021p

  日期：2013.12.20

  A nickel-catalyzed aromatic C-H alkylation with tertiary or secondary alkyl-Br bonds for the construction of indolones was demonstrated. Various functional groups were well tolerated. Moreover, the challenging secondary alkyl bromides were well introduced in this transformation. Radical trapping and photocatalysis conditions exhibited that it is most likely to be a radical process for this aromatic C-H alkylation.