2-octadecyl-1H-indole | 1195790-21-6

• 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: 2-octadecyl-1H-indole
• CAS: 1195790-21-6
• 化学式: C₂₆H₄₃N
• 分子量: 369.634
• InChiKey: KTPODUFSMKSQGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-octadecyl-1H-indole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以33%的产率得到2-octadecyl-2-(2-octadecyl-3-oxo-2,3-dihydro-1H-indol-2-yl)-1,2-dihydro-3H-indol-3-one
  参考文献：
  名称：

  Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin

  摘要：

  A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannyl-substituted 1-methoxy-1-alkene from a Fischer chromium carbene, intermolecular Kosugi-Migita-Stille coupling, and a palladium-catalyzed reductive N-heteroannulation. Demethylation of 3-methoxy-2-octadecylindole, a possible immediate precursor to 3-hydroxy-2-octadecylindole, was unsuccessful and gave instead methyl 2-(1-oxononadecanyl)aminobenzoate. The structure of the isolated alkaloid was suggested to be 2-(1-oxooctaclecanyl)aminobenzoate by comparison of analytical data with a synthetic sample. In addition. oxidation of 2-octadecylindole gave a 2,2'-dimer, a compound identical to previously prepared 3-hydroxy-2-octadecylindole. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.055
• 作为产物：
  描述：

  triethyl((E)-1-(2-nitrophenyl)icos-1-enyl)silane 在 1,10-菲罗啉 、 一氧化碳 、 1,3-双(二苯基膦)丙烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、607.99 kPa 条件下， 反应 16.0h， 以70%的产率得到2-octadecyl-1H-indole
  参考文献：
  名称：

  Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin

  摘要：

  A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannyl-substituted 1-methoxy-1-alkene from a Fischer chromium carbene, intermolecular Kosugi-Migita-Stille coupling, and a palladium-catalyzed reductive N-heteroannulation. Demethylation of 3-methoxy-2-octadecylindole, a possible immediate precursor to 3-hydroxy-2-octadecylindole, was unsuccessful and gave instead methyl 2-(1-oxononadecanyl)aminobenzoate. The structure of the isolated alkaloid was suggested to be 2-(1-oxooctaclecanyl)aminobenzoate by comparison of analytical data with a synthetic sample. In addition. oxidation of 2-octadecylindole gave a 2,2'-dimer, a compound identical to previously prepared 3-hydroxy-2-octadecylindole. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.055

文献信息

• [EN] BIS-AMINO ACID BASED COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ À BASE D'ACIDES AMINÉS BIS ET SON UTILISATION
  申请人：UNIV MISSOURI

  公开号：WO2017223098A1

  公开（公告）日：2017-12-28

  Compositions comprising bis(tryptophan) derivatives are provided that act as antimicrobials. Also provided are methods for reversing antibiotic resistance in a bacterium, or recovering or enhancing antimicrobial activity of an antibiotic against a variety of microbes, by co-administration with a bis(tryptophan) derivative.

  提供了包含双色氨酸衍生物的组合物，其作为抗微生物剂。同时还提供了一种通过与双色氨酸衍生物联合给药来逆转细菌的抗生素耐药性，或恢复或增强抗生素对各种微生物的抗微生物活性的方法。
• Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin
  作者：Ronald W. Clawson、Christopher A. Dacko、Robert E. Deavers、Novruz G. Akhmedov、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2009.08.055

  日期：2009.10

  A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannyl-substituted 1-methoxy-1-alkene from a Fischer chromium carbene, intermolecular Kosugi-Migita-Stille coupling, and a palladium-catalyzed reductive N-heteroannulation. Demethylation of 3-methoxy-2-octadecylindole, a possible immediate precursor to 3-hydroxy-2-octadecylindole, was unsuccessful and gave instead methyl 2-(1-oxononadecanyl)aminobenzoate. The structure of the isolated alkaloid was suggested to be 2-(1-oxooctaclecanyl)aminobenzoate by comparison of analytical data with a synthetic sample. In addition. oxidation of 2-octadecylindole gave a 2,2'-dimer, a compound identical to previously prepared 3-hydroxy-2-octadecylindole. (c) 2009 Elsevier Ltd. All rights reserved.