1-Methanesulfonyl-4-phenyl-1,2,3,6-tetrahydropyridine | 1217795-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-Methanesulfonyl-4-phenyl-1,2,3,6-tetrahydropyridine
• 英文别名: 1-methylsulfonyl-4-phenyl-3,6-dihydro-2H-pyridine
• CAS: 1217795-68-0
• 化学式: C₁₂H₁₅NO₂S
• mdl: MFCD21366520
• 分子量: 237.323
• InChiKey: GIJNSQWIEHCSKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Methanesulfonyl-4-phenyl-1,2,3,6-tetrahydropyridine 在 selenium(IV) oxide 、 Jones reagent 、 双氧水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 8.33h， 生成 (1-methanesulfonyl-4-methoxy-4-phenylpiperidin-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

文献信息

• Selectfluor-promoted fluorination of piperidinyl olefins
  作者：Meng-Yang Chang、Nien-Chia Lee、Ming-Fang Lee、Yu-Ping Huang、Chung-Han Lin

  DOI：10.1016/j.tetlet.2010.08.090

  日期：2010.11

  4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate (Selectfluor) is reported. Two transformations from endo-olefin 1 to allylic fluoride 3 and from exo-olefin 2 to fluorohydrin 6 proceed via allylic fluorination and fluorohydroxylation in moderate yields. It presents two novel reactions promoted by Selectfluor and broadens the scope of application.

  通过哌啶子基外表皮的处理，简单而直接地合成1-取代的4-芳基-5-氟-1,2,3,6-四氢吡啶（3）或1-取代的4-二芳基甲酰基-4-氟哌啶（6）-或内烯烃与1-氯甲基-4-氟-1,4-二氮鎓双环[2.2.2]辛烷双（四氟硼酸盐（的Selectfluor）报道从两次转变。内切α-烯烃1至烯丙基氟化物3和从外烯烃2至氟代醇6通过烯丙基氟化和氟羟基化进行中等收率。它展示了Selectfluor促进的两个新颖反应，并扩大了应用范围。
• 10.1021/ol1000721n
  作者：Chang, Meng-Yang、Lin, Chung-Han、Chen, Yeh-Long、Chang, Ching-Yao、Hsu, Ru-Ting

  DOI：10.1021/ol1000721n

  日期：——
• Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin
  作者：Meng-Yang Chang、Chung-Han Lin、Yeh-Long Chen

  DOI：10.1016/j.tetlet.2010.01.020

  日期：2010.3

  Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin with the modest yields is described. This facile strategy was also used to synthesize several 4-arylpyridines, 3-hydroxy-4-arylpyridines, and 3,4-diarylpyridines. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• 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.