1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,5,8,8a-hexahydroquinoline | 1313538-20-3

• 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: 1-benzenesulfonyl-4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,5,8,8a-hexahydroquinoline
• 英文别名: 1-(benzenesulfonyl)-4-[4-chloro-3-(trifluoromethyl)phenyl]-3,5,8,8a-tetrahydro-2H-quinoline
• CAS: 1313538-20-3
• 化学式: C₂₂H₁₉ClF₃NO₂S
• 分子量: 453.913
• InChiKey: ZFACMYFBCVOEIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(benzenesulfonyl)-4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-pyridine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 selenium(IV) oxide 、 lithium aluminium tetrahydride 、 Jones reagent 、 正丁基锂 、 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 9.41h， 生成 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

文献信息

• Synthesis of tetrahydrobenzoisoquinolinols, tetrahydropyrindines, and hexahydroquinolines from 4-aryltetrahydropyridines
  作者：Meng-Yang Chang、Ming-Fang Lee、Yeh-Long Chen

  DOI：10.1016/j.tet.2011.04.089

  日期：2011.6

  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.