di(tert-butyl) 1-oxo-1,3-dihydroazepino[3,4-b]indole-2,10-dicarboxylate | 519033-28-4

• 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: di(tert-butyl) 1-oxo-1,3-dihydroazepino[3,4-b]indole-2,10-dicarboxylate
• 英文别名: di-tert-butyl 1-oxo-1,3-dihydroazepino[3,4-b]indole-2,10-dicarboxylate；(Z)-di-tert-butyl 1-oxoazepino[3,4-b]indole-2,10(1H,3H)-dicarboxylate；di-tert-butyl 1-oxoazepino[3,4-b]indole-2,10(1H,3H)-dicarboxylate；ditert-butyl 1-oxo-3H-azepino[3,4-b]indole-2,10-dicarboxylate
• CAS: 519033-28-4
• 化学式: C₂₂H₂₆N₂O₅
• 分子量: 398.459
• InChiKey: LGWQCRGMGDZYSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di(tert-butyl) 1-oxo-1,3-dihydroazepino[3,4-b]indole-2,10-dicarboxylate 在 potassium sulfate 、 potassium hydrogensulfate 、 oxone 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以83%的产率得到di-tert-butyl 4-oxo-1a,2,4,9c-tetrahydrooxireno[2',3':5,6]azepino[3,4-b]indole-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of novel hymenialdisine analogues using solvent-free and silica gel-promoted ring opening of epoxides

  摘要：

  A silica gel-promoted regioselective ring-opening reaction of epoxides with indoles and pyrrole under mild and solvent-free conditions is described. This reaction provides a synthetic pathway for a diverse class of novel hymenialdisine analogues. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.092
• 作为产物：
  描述：

  tert-butyl 2-{[(allyl-tert-butoxycarbonyl)amino]carbonyl}-3-vinyl-1H-indole-1-carboxylate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以60%的产率得到di(tert-butyl) 1-oxo-1,3-dihydroazepino[3,4-b]indole-2,10-dicarboxylate
  参考文献：
  名称：

  吲哚2-羧酸烯丙基酰胺衍生物的闭环复分解

  摘要：

  3-烯丙基或3-乙烯基吲哚-2-羧酸衍生物的闭环易位使得可以得到稠合的七元至八元内酰胺。1-烯丙基吲哚-2-羧酸高烯丙基酰胺得到九元内酰胺。还研究了1，3-二取代-2-羧酸衍生物的反应性。

  DOI：

  10.1016/s0040-4020(02)01404-7

文献信息

• Preparation of Novel Unsymmetrical Bisindoles under Solvent-Free Conditions:  Synthesis, Crystal Structures, and Mechanistic Aspects
  作者：Hanns Martin Kaiser、Ivo Zenz、Wei Fun Lo、Anke Spannenberg、Kristin Schröder、Haijun Jiao、Dirk Gördes、Matthias Beller、Man Kin Tse

  DOI：10.1021/jo7016026

  日期：2007.11.1

  O-nucleophiles demonstrate their versatility as key intermediates in diversity oriented synthesis. The hydroxyl precursor leads also to unsymmetrical bisindoles under similar reaction conditions. Important intermediates and final library compounds were confirmed by X-ray analysis. Theoretical studies on these systems show the possible cationic intermediate in the substitution pathway.

  吲哚氮丙啶及其羟基衍生物已用于制备新型官能化双吲哚的小型文库。在温和的反应条件下，通过无溶剂的C-C键在固体支持物上形成这些结构单元的多样化，产生了环状的Hymenialdisine类似物。作为C-亲核试剂的吲哚通过亲电子芳族取代途径以良好或优异的收率形成潜在的药理活性双吲哚。H-，N-和O进一步转化吲哚氮丙啶-亲核试剂证明了其作为多样性导向合成中的关键中间体的多功能性。羟基前体在相似的反应条件下也导致不对称的双吲哚。通过X射线分析证实了重要的中间体和最终的文库化合物。对这些系统的理论研究表明，取代途径中可能存在阳离子中间体。
• New Synthetic Protocols for the Preparation of Unsymmetrical Bisindoles
  作者：Hanns Martin Kaiser、Wei Fun Lo、Abdol Majid Riahi、Anke Spannenberg、Matthias Beller、Man Kin Tse

  DOI：10.1021/ol062338p

  日期：2006.12.1

  Novel unsymmetrical bisindoles were synthesized by a solvent-free C-C bond-formation reaction under mild conditions. Starting from aziridines or hydroxyl precursors, indoles have been used as C-nucleophiles to form new pharmacologically interesting bisindoles via an electrophilic aromatic substitution pathway in good to excellent yields.
• Synthesis of novel hymenialdisine analogues using solvent-free and silica gel-promoted ring opening of epoxides
  作者：Naveenkumar Mangu、Hanns Martin Kaiser、Anirban Kar、Anke Spannenberg、Matthias Beller、Man Kin Tse

  DOI：10.1016/j.tet.2008.05.092

  日期：2008.7

  A silica gel-promoted regioselective ring-opening reaction of epoxides with indoles and pyrrole under mild and solvent-free conditions is described. This reaction provides a synthetic pathway for a diverse class of novel hymenialdisine analogues. (c) 2008 Elsevier Ltd. All rights reserved.
• Ring closure metathesis of indole 2-carboxylic acid allylamide derivatives
  作者：Lidwine Chacun-Lefèvre、Valérie Bénéteau、Benoı̂t Joseph、Jean-Yves Mérour

  DOI：10.1016/s0040-4020(02)01404-7

  日期：2002.12

  Ring-closing metathesis of 3-allyl- or 3-vinylindole-2-carboxylic derivatives gave access to fused seven- to eight-membered lactams; 1-allylindole-2-carboxylic homoallylamide afforded the nine-membered lactam. The reactivity of 1,3-disubstituted-2-carboxylic acid derivatives was also investigated.

  3-烯丙基或3-乙烯基吲哚-2-羧酸衍生物的闭环易位使得可以得到稠合的七元至八元内酰胺。1-烯丙基吲哚-2-羧酸高烯丙基酰胺得到九元内酰胺。还研究了1，3-二取代-2-羧酸衍生物的反应性。