N-(2-(benzo[d][1,3]dioxol-5-yl)-2-(4-chlorophenyl)ethyl)-4-methylbenzenesulfonamide

• 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-(2-(benzo[d][1,3]dioxol-5-yl)-2-(4-chlorophenyl)ethyl)-4-methylbenzenesulfonamide
• 英文别名: N-[2-(1,3-benzodioxol-5-yl)-2-(4-chlorophenyl)ethyl]-4-methylbenzenesulfonamide
• 化学式: C₂₂H₂₀ClNO₄S
• 分子量: 429.924
• InChiKey: QUZFKMMNHOAYKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对溴苯甲醛 、 N-(2-(benzo[d][1,3]dioxol-5-yl)-2-(4-chlorophenyl)ethyl)-4-methylbenzenesulfonamide 在 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以56%的产率得到
  参考文献：
  名称：

  Lewis acid promoted three-component reactions of aziridines, arenes and aldehydes: an efficient and diastereoselective synthesis of cis-1,4-disubstituted tetrahydroisoquinolines

  摘要：

  A new Lewis acid promoted three-component reaction between the aziridine, arene and aldehyde has been developed. This reaction involves sequential ring opening of aziridine and Pictet-Spengler condensation and gives a broad range of cis-1,4-disubstituted tetrahydroisoquinolines in moderate yields with good diastereoselectivities under mild conditions. The methodology provides a rapid and convergent synthesis for the scaffold of tetrahydroisoquinoline and serves as a good tool for constructing the libraries of substituted tetrahydroisoquinolines. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.013
• 作为产物：
  描述：

  胡椒环 、 N-(p-toluenesulfonyl)-2-(4-chlorophenyl)aziridine 在 gold(III) chloride 、 silver trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 反应 0.03h， 以89%的产率得到N-(2-(benzo[d][1,3]dioxol-5-yl)-2-(4-chlorophenyl)ethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  氯化金/三氟甲磺酸银：氮丙啶与电子富集的芳烃开环反应的高效催化剂

  摘要：

  发现氯化金（III）/三氟甲磺酸银是在氮丙啶与富电子芳烃的开环中作为高效催化剂的催化剂，在温和的反应条件下，以良好或极好的收率提供了所需的β-芳基胺。

  DOI：

  10.1002/adsc.200700101

文献信息

• FeCl3: an efficient catalyst for reactions of electron-rich arenes with imines or aziridines
  作者：Zhiyong Wang、Xiaoyu Sun、Jie Wu

  DOI：10.1016/j.tet.2008.03.081

  日期：2008.5

  Iron(III) chloride was discovered highly effective as catalyst in the Friedel-Crafts reactions of electron-rich arenes with imines or aziridines. It was found that reactions of imines were highly substrate-dependent, which generated mono- or double-addition products, while arenes reacted with aziridines regioselectively leading to the formation of desired ring-opening products in 2 min with moderate to good yields. (C) 2008 Elsevier Ltd. All rights reserved.
• First examples of C-arylation of aziridines catalyzed by indium triflate
  作者：J.S Yadav、B.V Subba Reddy、R Srinivasa Rao、G Veerendhar、K Nagaiah

  DOI：10.1016/s0040-4039(01)01699-9

  日期：2001.11

  Aziridines react smoothly with arenes in the presence of a catalytic amount of indium triflate at ambient temperature to afford the corresponding P-aryl amine derivatives in excellent yields with high regioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.