(S)-2-allyl-1,2,3,4-tetrahydroquinoline | 1548395-98-7

• 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-allyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (2S)-2-prop-2-enyl-1,2,3,4-tetrahydroquinoline
• CAS: 1548395-98-7
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: SKVKLIVRXCNENZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-allyl-1,2,3,4-tetrahydroquinoline 在 Hoveyda-Grubbs catalyst second generation 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-4,4a,5,6-tetrahydro-1H-pyrido[1,2-a]quinolin-1-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：

  (S)-N-(3-(2-bromophenyl)propylidene)-2-methylpropane-2-sulfinamide 在 盐酸 、 indium 、 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 28.0h， 生成 (S)-2-allyl-1,2,3,4-tetrahydroquinoline
  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

文献信息

• Bio-mediated oxidative resolution of racemic 2-substituted 1,2,3,4-tetrahydroquinolines
  作者：Lei Qin、Daijun Zheng、Baodong Cui、Nanwei Wan、Xiaojian Zhou、Yongzheng Chen

  DOI：10.1016/j.tetlet.2016.04.066

  日期：2016.6

  Whole cell of Pseudomonas monteilii ZMU-T01 strains mediated oxidative resolution of racemic 2-substituted 1,2,3,4-tetrahydroquinolines has been successfully described. A series of highly enantioselective 2-substituted 1,2,3,4-tetrahydroquinoline derivatives were obtained in up to 50% conversion and >99% ee.

  已经成功地描述了蒙特氏假单胞菌ZMU -T01菌株的全细胞介导的外消旋2-取代的1,2,3,4-四氢喹啉的氧化拆分。以高达50％的转化率和> 99％的ee获得了一系列高度对映选择性的2-取代的1,2,3,4-四氢喹啉衍生物。