N-(2-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide | 1280171-15-4

• 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-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]-N-methyl-4-nitrobenzenesulfonamide
• CAS: 1280171-15-4
• 化学式: C₁₇H₁₇N₃O₄S
• 分子量: 359.406
• InChiKey: PNISTLCPXFNGQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide 在 1,4-二甲基哌嗪 、 N-氯代丁二酰亚胺 、 sodium hydride 、 caesium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.25h， 生成 3-(2-(methylamino)ethyl)-3-reverse-prenyl-N-prenyl oxindole
  参考文献：
  名称：

  Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy

  摘要：

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.020
• 作为产物：
  描述：

  色胺 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-(2-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy

  摘要：

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.020

文献信息

• Catalytic Asymmetric Friedel–Crafts Alkylation of Indole via In Situ Generated Indol‐2‐one
  作者：Yuanai Fei、Jun Hou、Huiying Song、Mei‐li Yang、Pan Lei、Xiayu Ge、Hongbo Wei、Yuanzhen Xu、Weiqing Xie

  DOI：10.1002/ejoc.202300122

  日期：2023.3.21

  Friedel–Crafts alkylation of indole derivatives with in situ generated indol-2-ones from functionalized 3-bromooxinidoles to construct 3-substituted 3’-indolyloxindole skeleton catalyzed by chiral N,N’-dioxide/Ni(BF4)2 has been developed, which enabled the formal synthesis of (+)-folicanthine.

  吲哚衍生物的不对称 Friedel-Crafts 烷基化与原位生成的 indol-2-ones 从功能化的 3-bromooxinidoles 构建 3-取代的 3'-indolyloxindole 骨架由手性 N,N'-dioxide/Ni( BF 4 ) 2催化具有已经开发出来，这使得 (+)-folicanthine 的正式合成成为可能。
• Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy
  作者：Vasily A. Ignatenko、Ping Zhang、Rajesh Viswanathan

  DOI：10.1016/j.tetlet.2011.01.020

  日期：2011.3

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.