N-methyl-N-(2-(3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)ethyl)-4-nitrobenzenesulfonamide | 1280171-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-methyl-N-(2-(3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)ethyl)-4-nitrobenzenesulfonamide
• CAS: 1280171-16-5
• 化学式: C₂₂H₂₅N₃O₅S
• 分子量: 443.524
• InChiKey: ZTPZZNGALDZISQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  109.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(2-(3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)ethyl)-4-nitrobenzenesulfonamide 在 alane N,N-dimethylethylamine complex 、 sodium hydride 、 caesium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 4.25h， 生成 (+/-)-1-methyl-3a-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)-1,2,3,3a-tetrahydropyrrolo[2,3-b]indole
  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 1,4-二甲基哌嗪 、 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-methyl-N-(2-(3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)ethyl)-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 Reverse Prenylation of Indol-2-one Enabled a Synthesis of (−)-Debromoflustramine A
  作者：Yi Hou、Jiyou Huo、Ruoxin Li、Jun Hou、Pan Lei、Hongbo Wei、Weiqing Xie

  DOI：10.1021/acs.orglett.3c02296

  日期：2023.9.29

  A catalytic asymmetric nucleophilic reverse prenylation of indol-2-ones in situ generated from 3-bromooxindoles with prenyltributylstannane promoted by Ni(II)/chiral N,N′-dioxide was developed. This reaction provides facile access to C3 reverse-prenylated oxindoles in good to excellent enantioselectivities, which enabled the asymmetric synthesis of debromoflustramine A in five steps.

  开发了由 Ni(II)/手性N,N'-二氧化物促进的异戊烯基三丁基锡烷对 3-溴氧吲哚产生的吲哚-2-酮原位催化不对称亲核反异戊二烯化反应。该反应以良好至优异的对映选择性方便地获得 C3 反向异戊二烯化羟吲哚，从而能够通过五个步骤不对称合成去溴氟曲明 A。