(S)-2-methylene-3,3a,4,5-tetrahydropyrrolo[1,2-a]quinolin-1(2H)-one | 1548393-02-7

• 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: (S)-2-methylene-3,3a,4,5-tetrahydropyrrolo[1,2-a]quinolin-1(2H)-one
• CAS: 1548393-02-7
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: HIPRPQSAGNQUDR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (S)-N-(3-(2-bromophenyl)propylidene)-2-methylpropane-2-sulfinamide 在 盐酸 、 indium 、 copper(l) iodide 、 potassium carbonate 、 sodium bromide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 71.0h， 生成 (S)-2-methylene-3,3a,4,5-tetrahydropyrrolo[1,2-a]quinolin-1(2H)-one
  参考文献：
  名称：

  Stereoselective Synthesis of Indoline, Tetrahydroquinoline, and Tetrahydrobenzazepine Derivatives from o-Bromophenyl N-tert-Butylsulfinyl Aldimines

  摘要：

  The diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substituted heterocycles 14 could also be prepared by means of a palladium-catalyzed N-arylation of the corresponding free amines. The synthesis of the alkaloid (-)-angustureine was easily accomplished from (S)-2-allyltetrahydroquinoline (14b).

  DOI：

  10.1021/jo402759v