[1',1',1'-(2)H3]-1-methoxyindole | 253305-65-6

• 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: [1',1',1'-(2)H3]-1-methoxyindole
• 英文别名: 1-[2H3]methoxyindole
• CAS: 253305-65-6
• 化学式: C₉H₉NO
• 分子量: 150.153
• InChiKey: GTVWPXDPNQJYNV-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  14.16
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [1',1',1'-(2)H3]-1-methoxyindole 在 sodium tetrahydroborate 、 ammonium acetate 、 silica gel 、 三氯氧磷 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 4.0h， 生成 3-(2-nitroethyl)-1-[2H3]methoxyindole
  参考文献：
  名称：

  氘标记的去磺基芥子油苷的合成作为LC-MS分析的内标

  摘要：

  描述了三种氘标记的去磺基硫代葡萄糖苷的合成。这些是苯乙基，1-甲氧基吲哚基和4-甲氧基吲哚基衍生物。制备这些化合物作为内标，用于芥子油苷的定量LC-MS分析，以提高分析程序的灵敏度。

  DOI：

  10.1016/s0040-4020(99)00817-0
• 作为产物：
  描述：

  甲基硝基苯 在 sodium hydroxide 、 甲基三辛基氯化铵 、 氯化铵 、 锌 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 [1',1',1'-(2)H3]-1-methoxyindole
  参考文献：
  名称：

  氘标记的去磺基芥子油苷的合成作为LC-MS分析的内标

  摘要：

  描述了三种氘标记的去磺基硫代葡萄糖苷的合成。这些是苯乙基，1-甲氧基吲哚基和4-甲氧基吲哚基衍生物。制备这些化合物作为内标，用于芥子油苷的定量LC-MS分析，以提高分析程序的灵敏度。

  DOI：

  10.1016/s0040-4020(99)00817-0

文献信息

• The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: De novo incorporation of deuterated tryptophans and quasi-natural compounds
  作者：M. Soledade C. Pedras、Denis P. Okinyo-Owiti、Ken Thoms、Adewale M. Adio

  DOI：10.1016/j.phytochem.2009.05.015

  日期：2009.6

  Although several biosynthetic intermediates in pathways to cruciferous phytoalexins and phytoanticipins are common, questions regarding the introduction of substituents at N-1 of the indole moiety remain unanswered. Toward this end, we investigated the potential incorporations of several perdeuterated D- and L-1'-methoxytryptophans, D- and L-tryptophans and other indol-3-yl derivatives into pertinent phytoalexins and phytoanticipins (indolyl glucosinolates) produced in rutabaga (Brassica napus L. ssp. rapifera) roots. In addition, we probed the potential transformations of quasi-natural compounds, these being analogues of biosynthetic intermediates that might lead to "quasi-natural" products (products similar to natural products but not produced under natural conditions). No detectable incorporations of deuterium labeled 1'-methoxytryptophans into phytoalexins or glucobrassicin were detected. L-tryptophan was incorporated in a higher percentage than D-tryptophan into both phytoalexins and phytoanticipins. However, in the case of the phytoalexin rapalexin A, both D- and L-tryptophan were incorporated to the same extent. Furthermore, the transformations of both 1'-methylindolyl-3'-acetaldoxime and 1'-methylindolyl-3'-acetothiohydroxamic acid (quasi-natural products) into 1'-methylglucobrassicin but not into phytoalexins suggested that post-aldoxime enzymes in the biosynthetic pathway of indolyl glucosinolates are not substrate-specific. Hence, it would appear that the 1-methoxy substituent of the indole moiety is introduced downstream from tryptophan and that the post-aldoxime enzymes of the glucosinolate pathway are different from the enzymes of the phytoalexin pathway. A higher substrate specificity of some enzymes of the phytoalexin pathway might explain the relatively lower structural diversity among phytoalexins than among glucosinolates. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of deuterium labelled desulfoglucosinolates as internal standards for LC-MS analysis
  作者：Avril A.B. Robertson、Nigel P. Botting

  DOI：10.1016/s0040-4020(99)00817-0

  日期：1999.11

  The syntheses of three deuterium labelled desulfoglucosinolates are described. These are the phenethyl, 1-methoxyindolyl and 4-methoxyindolyl derivatives. The compounds were prepared as internal standards for use in the quantitative LC-MS analysis of glucosinolates to improve the sensitivity of the analytical procedure.

  描述了三种氘标记的去磺基硫代葡萄糖苷的合成。这些是苯乙基，1-甲氧基吲哚基和4-甲氧基吲哚基衍生物。制备这些化合物作为内标，用于芥子油苷的定量LC-MS分析，以提高分析程序的灵敏度。