[2-allyl-1-benzenesulfonyl-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridin-3-yl]acetic acid ethyl ester | 1313537-81-3

• 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: [2-allyl-1-benzenesulfonyl-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridin-3-yl]acetic acid ethyl ester
• 英文别名: ethyl 2-[1-(benzenesulfonyl)-6-prop-2-enyl-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-pyridin-5-yl]acetate
• CAS: 1313537-81-3
• 化学式: C₂₅H₂₆F₃NO₄S
• 分子量: 493.547
• InChiKey: PVEJZYIOAYOHGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [2-allyl-1-benzenesulfonyl-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridin-3-yl]acetic acid ethyl ester 在 lithium aluminium tetrahydride 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到2-(2-allyl-1-benzenesulfonyl-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridin-3-yl)ethanol
  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：

  1-(benzenesulfonyl)-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-pyridine 在 selenium(IV) oxide 、 Jones reagent 、 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.91h， 生成 [2-allyl-1-benzenesulfonyl-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridin-3-yl]acetic acid ethyl ester
  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.