(4S,S_S)-ethyl N-(tert-butylsulfinyl)-4-amino-7-(2-bromophenyl)-2-methyleneheptanoate | 1548392-47-7

• 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: (4S,S_S)-ethyl N-(tert-butylsulfinyl)-4-amino-7-(2-bromophenyl)-2-methyleneheptanoate
• CAS: 1548392-47-7
• 化学式: C₂₀H₃₀BrNO₃S
• 分子量: 444.433
• InChiKey: HLJFDHDFVJHLDW-QLXKLKPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4S,S_S)-ethyl N-(tert-butylsulfinyl)-4-amino-7-(2-bromophenyl)-2-methyleneheptanoate 在 盐酸 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到(S)-5-(3-bromophenylpropyl)-3-methylenepyrrolidin-2-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
• 作为产物：
  描述：

  4-苯基丁醛 在 titanium(IV) tetraethanolate 、 indium 、 sodium bromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 (4S,S_S)-ethyl N-(tert-butylsulfinyl)-4-amino-7-(2-bromophenyl)-2-methyleneheptanoate
  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