5,6-diallyl-1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine | 1313538-16-7

• 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: 5,6-diallyl-1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine
• CAS: 1313538-16-7
• 化学式: C₂₄H₂₃ClF₃NO₂S
• 分子量: 481.966
• InChiKey: QNLVHZMDNZERRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5,6-diallyl-1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 1,2-二氯乙烷 为溶剂， 以62%的产率得到1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,5,8,8a-hexahydroquinoline
  参考文献：
  名称：

  Synthesis of tetrahydrobenzoisoquinolinols, tetrahydropyrindines, and hexahydroquinolines from 4-aryltetrahydropyridines

  摘要：

  A straightforward synthesis of tetrahydrobenzoisoquinolinols 2, tetrahydropyrindines 3, and hexahydroquinolines 4 from versatile intermediate 6 is reported. Two key transformations were carried out by intramolecular Friedel-Crafts cyclization and ring-closing metathesis in moderate yields. Skeleton 6 was easily prepared from the known starting material 4-aryl-4-methoxypiperidin-3-ones 7 via Wittig olefination with Ph3P=CHCO2Et, deconjugation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF3-OEt2)-catalyzed addition of the corresponding iminium ion with allyltrimethylsilane. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.089
• 作为产物：
  描述：

  2-(2-allyl-1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridin-3-yl)ethanol 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 5,6-diallyl-1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Synthesis of tetrahydrobenzoisoquinolinols, tetrahydropyrindines, and hexahydroquinolines from 4-aryltetrahydropyridines

  摘要：

  A straightforward synthesis of tetrahydrobenzoisoquinolinols 2, tetrahydropyrindines 3, and hexahydroquinolines 4 from versatile intermediate 6 is reported. Two key transformations were carried out by intramolecular Friedel-Crafts cyclization and ring-closing metathesis in moderate yields. Skeleton 6 was easily prepared from the known starting material 4-aryl-4-methoxypiperidin-3-ones 7 via Wittig olefination with Ph3P=CHCO2Et, deconjugation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF3-OEt2)-catalyzed addition of the corresponding iminium ion with allyltrimethylsilane. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.089