14-(4',6'-dimethoxy-1'H-indol-1'-yl)tetradecan-2-one | 944128-42-1

• 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: 14-(4',6'-dimethoxy-1'H-indol-1'-yl)tetradecan-2-one
• 英文别名: 14-(4,6-Dimethoxyindol-1-yl)tetradecan-2-one
• CAS: 944128-42-1
• 化学式: C₂₄H₃₇NO₃
• 分子量: 387.563
• InChiKey: NGMRHLSVQDAGQR-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C
• 沸点：
  528.7±30.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  14-(4',6'-dimethoxy-1'H-indol-1'-yl)tetradecan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以83%的产率得到14-(4',6'-dimethoxy-1'H-indol-1'-yl)tetradecan-2-ol
  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：

  1-(9'-decen-1'-yl)-4,6-dimethoxy-1H-indole 在 四丙基高钌酸铵 、 palladium dichloride 1,1-二溴乙烷 、 偶氮二异丁腈 、 dimethyl sulfide borane 、 4 A molecular sieve 、 碘 、 氧气 、 三正丁基氢锡 、 magnesium 、 N-甲基吗啉氧化物 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 32.25h， 生成 14-(4',6'-dimethoxy-1'H-indol-1'-yl)tetradecan-2-one
  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

• Synthesis of indole analogues of the anti-Helicobacter pylori compounds CJ-13,015, CJ-13,102, CJ-13,104 and CJ-13,108
  作者：Zoe E. Wilson、Amanda M. Heapy、Margaret A. Brimble

  DOI：10.1016/j.tet.2007.04.067

  日期：2007.6

  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.