N-(4-methoxybenzyl)-4-methyl-N-(3-oxopropyl)benzenesulfonamide | 1378478-43-3

• 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: N-(4-methoxybenzyl)-4-methyl-N-(3-oxopropyl)benzenesulfonamide
• CAS: 1378478-43-3
• 化学式: C₁₈H₂₁NO₄S
• 分子量: 347.435
• InChiKey: CFNFPPVNWVKDMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-4-methyl-N-(3-oxopropyl)benzenesulfonamide 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成
  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：

  在 二异丁基氢化铝 、 水 、 rochelle salt 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 N-(4-methoxybenzyl)-4-methyl-N-(3-oxopropyl)benzenesulfonamide
  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

• An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel–Crafts-type addition to 3-alkylidene indolenium cations
  作者：Takuya Yokosaka、Tetsuhiro Nemoto、Yasumasa Hamada

  DOI：10.1039/c2cc31699d

  日期：——

  An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives

  描述了一种酸促进的新型骨骼重排。使用三氟乙酸作为酸促进剂，将分子内的ipso-Friedel-Crafts型酚添加到3-亚烷基吲哚阳离子中，通过螺环己二烯酮单元的重新芳构化形成亚胺阳离子，并依次进行分子内的Pictet-Spengler反应，从而生成三环吲哚衍生品。
• Synthesis of fused-tricyclic indole derivatives through an acid-promoted skeletal rearrangement
  作者：Takuya Yokosaka、Tomoya Kanehira、Hiroki Nakayama、Tetsuhiro Nemoto、Yasumasa Hamada

  DOI：10.1016/j.tet.2014.01.074

  日期：2014.3

  We developed a novel method for synthesizing fused-tricyclic indole derivatives with a 3-aminomethyl indole motif through a reaction cascade involving ipso-Friedel-Crafts alkylation of phenols, rearomatization of the spirocyclohexadienone unit, and iso-Pictet-Spengler reaction. Using TFA as an acid promoter, six-, seven-, and eight-membered ring-fused indoles were obtained in 31-99% yield. (C) 2014 Elsevier Ltd. All rights reserved.