N-[(E)-5-hydroxy-5-phenylpent-3-enyl]-N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide | 1424888-15-2

• 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: N-[(E)-5-hydroxy-5-phenylpent-3-enyl]-N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide
• CAS: 1424888-15-2
• 化学式: C₂₆H₂₉NO₄S
• 分子量: 451.587
• InChiKey: WVXHETWZBHVCFM-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(E)-5-hydroxy-5-phenylpent-3-enyl]-N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 以89.474%的产率得到
  参考文献：
  名称：

  A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement

  摘要：

  A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to allyl cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and an intramolecular aza-Prins reaction, proceeded sequentially to afford 3-arylpyrrolidine and 4-arylpiperidine derivatives in good yield with high diastereoselectivity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.034
• 作为产物：
  描述：

  N-(4-methoxybenzyl)-4-methyl-N-(3-oxopropyl)benzenesulfonamide 在 manganese(IV) oxide 、 二异丁基氢化铝 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 N-[(E)-5-hydroxy-5-phenylpent-3-enyl]-N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement

  摘要：

  A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to allyl cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and an intramolecular aza-Prins reaction, proceeded sequentially to afford 3-arylpyrrolidine and 4-arylpiperidine derivatives in good yield with high diastereoselectivity. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.034

文献信息

• A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement
  作者：Takuya Yokosaka、Tetsuhiro Nemoto、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2013.01.034

  日期：2013.3

  A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to allyl cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and an intramolecular aza-Prins reaction, proceeded sequentially to afford 3-arylpyrrolidine and 4-arylpiperidine derivatives in good yield with high diastereoselectivity. (c) 2013 Elsevier Ltd. All rights reserved.