N-(5-(5-benzyloxy-1H-indol-3-yl)-1-oxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-4-yl)tosylamide

• 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-(5-(5-benzyloxy-1H-indol-3-yl)-1-oxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-4-yl)tosylamide
• 英文别名: 4-methyl-N-[(4S,5R)-1-oxo-5-(5-phenylmethoxy-1H-indol-3-yl)-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-4-yl]benzenesulfonamide
• 化学式: C₃₄H₃₀N₄O₄S
• 分子量: 590.703
• InChiKey: SSYZZCXDFWPHMN-JSOSNVBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  di(tert-butyl) 1-oxo-1,3-dihydroazepino[3,4-b]indole-2,10-dicarboxylate 在 silica gel 、 phenyltrimethylammonium tribromide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 13.0h， 生成 N-(5-(5-benzyloxy-1H-indol-3-yl)-1-oxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-4-yl)tosylamide
  参考文献：
  名称：

  New Synthetic Protocols for the Preparation of Unsymmetrical Bisindoles

  摘要：

  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.

  DOI：

  10.1021/ol062338p

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.