[1-benzenesulfonyl-4-methoxy-4-(4-chloro-3-trifluoromethylphenyl)piperidin-3-ylidene]acetic acid ethyl ester | 1313537-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [1-benzenesulfonyl-4-methoxy-4-(4-chloro-3-trifluoromethylphenyl)piperidin-3-ylidene]acetic acid ethyl ester
• CAS: 1313537-75-5
• 化学式: C₂₃H₂₃ClF₃NO₅S
• 分子量: 517.954
• InChiKey: KBTBAUQRVYUDPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [1-benzenesulfonyl-4-methoxy-4-(4-chloro-3-trifluoromethylphenyl)piperidin-3-ylidene]acetic acid ethyl ester 在 lithium aluminium tetrahydride 、 正丁基锂 、 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 为溶剂， 反应 1.08h， 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
• 作为产物：
  描述：

  (3S,4R)-1-(benzenesulfonyl)-4-[4-chloro-3-(trifluoromethyl)phenyl]-4-methoxypiperidin-3-ol 在 Jones reagent 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.33h， 生成 [1-benzenesulfonyl-4-methoxy-4-(4-chloro-3-trifluoromethylphenyl)piperidin-3-ylidene]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