1-(9'-decen-1'-yl)-4,6-dimethoxy-1H-indole | 944128-32-9

• 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: 1-(9'-decen-1'-yl)-4,6-dimethoxy-1H-indole
• 英文别名: 1-Dec-9-enyl-4,6-dimethoxyindole；1-dec-9-enyl-4,6-dimethoxyindole
• CAS: 944128-32-9
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: ILHOCUWBWZOAAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(9'-decen-1'-yl)-4,6-dimethoxy-1H-indole 在 四丙基高钌酸铵 、 palladium dichloride 4-二甲氨基吡啶 、 1,1-二溴乙烷 、 dimethyl sulfide borane 、 4 A molecular sieve 、 碘 、 氧气 、 magnesium 、 N-甲基吗啉氧化物 、 copper(l) chloride 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.25h， 生成 14-(4',6'-dimethoxy-1'H-indol-1'-yl)-2-oxo-tetradecan-5-yl acetate
  参考文献：
  名称：

  Synthesis of indole analogues of the anti-Helicobacter pylori compounds CJ-13,015, CJ-13,102, CJ-13,104 and CJ-13,108

  摘要：

  Racemic syntheses of indole analogues of four phthalide-containing anti-Helicobacter pylori agents CJ-13,015, CJ-13,102, CJ-13,104 and CJ-13,108 are reported via manipulation of a common intermediate. This intermediate was formed by the N-alkylation of 4,6-dimethoxyindole with a long chain bromide followed by further chain extension. Oxidation, acetylation, or Barton-McCombie deoxygenation of the intermediate followed by Wacker oxidation afforded three analogues whilst further reduction of one analogue afforded the final analogue. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.067
• 作为产物：
  描述：

  9-十烯-1-醇 在 氢氧化钾 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 1-(9'-decen-1'-yl)-4,6-dimethoxy-1H-indole
  参考文献：
  名称：

  Synthesis of indole analogues of the anti-Helicobacter pylori compounds CJ-13,015, CJ-13,102, CJ-13,104 and CJ-13,108

  摘要：

  Racemic syntheses of indole analogues of four phthalide-containing anti-Helicobacter pylori agents CJ-13,015, CJ-13,102, CJ-13,104 and CJ-13,108 are reported via manipulation of a common intermediate. This intermediate was formed by the N-alkylation of 4,6-dimethoxyindole with a long chain bromide followed by further chain extension. Oxidation, acetylation, or Barton-McCombie deoxygenation of the intermediate followed by Wacker oxidation afforded three analogues whilst further reduction of one analogue afforded the final analogue. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.067

文献信息

• Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015
  作者：Fiona J. Radcliff、John D. Fraser、Zoe E. Wilson、Amanda M. Heapy、James E. Robinson、Christina J. Bryant、Christopher L. Flowers、Margaret A. Brimble

  DOI：10.1016/j.bmc.2008.04.037

  日期：2008.6

  The naturally occurring phthalide-containing antibiotics spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,015, CJ-13,102, CJ-13,103, CJ-13,104 and CJ-13,108, have been reported to exhibit anti-H. pylori activity. However, the exact stereochemistry of spirolaxine methyl ether, CJ-12,954 or CJ-13,013, contributing to this observed activity has not been confirmed. The anti-H. pylori activity of several analogues of spirolaxine methyl ether, CJ-12,954 and CJ-13,013 of defined stereochemistry together with the anti-H. pylori activity of several indole analogues of the simpler phthalide-containing antibiotics CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015 is reported herein. A 1:1 mixture of spiroacetals 5b and 6b in which the phthalide substituent exhibited (3R)-stereochemistry was sixty times more active than the corresponding 1:1 mixture of spiroacetals with (3S)-stereochemistry. Notably, the unnatural (2 '' S)-diastereomer of spirolaxine methyl ether exhibited more potent anti-H. pylori activity than the natural product spirolaxine methyl ether. The 4,6-dimethoxyindoles 9, 10, 11 and 13 were all found to be less active than their parent compounds 1, 2, 3 and 4, respectively. Chain-shortened 4,6-dimethoxyindole analogue 12 of CJ-13,108 3 and 4,6-dimethoxyindole-spiroacetal 13 exhibited weak anti-H. pylori activity thus providing future opportunity for drug discovery programs. (C) 2008 Elsevier Ltd. All rights reserved.