[3,4,5,6-(2)H4]-2-nitrophenylacetonitrile | 927182-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3,4,5,6-(2)H4]-2-nitrophenylacetonitrile
• 英文别名: [3,4,5,6-2H4]2-nitrophenyl-acetonitrile
• CAS: 927182-47-6
• 化学式: C₈H₆N₂O₂
• 分子量: 166.116
• InChiKey: YPRFCQAWSNWRLM-RHQRLBAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [3,4,5,6-(2)H4]-2-nitrophenylacetonitrile 在 palladium on activated charcoal 盐酸 、 copper-zinc-aluminum 、 氢气 、 羟胺 、 三乙胺 、 三氯氧磷 作用下， 生成 [4',5',6',7'-²H₄]brassinin
  参考文献：
  名称：

  十字花科植物抗毒素黄铜素和环油菜素是黄铜素生物合成的中间体。

  摘要：

  在用四氘化十字花科植物抗毒素黄铜素（5b）和环花青素（6b）进行饲喂实验后，用引起细菌真菌Phoma lingam的黑腿引发了芸苔属的叶子。光谱和HPLC分析表明，在十字花科植物抗毒素黄铜素（7a）中掺入了油菜素（5a）和环油菜素（6a）。

  DOI：

  10.1016/s0960-894x(98)00564-2
• 作为产物：
  描述：

  硝基苯-d5 、 氯乙腈 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 [2,3,5,6‐D₄]‐4‐nitrophenylacetonitrile 、 [3,4,5,6-(2)H4]-2-nitrophenylacetonitrile
  参考文献：
  名称：

  Syntheses of perdeuterated indoles and derivatives as probes for the biosyntheses of crucifer phytoalexins

  摘要：

  开发了一种简单的两步制备[2H4]吲哚的方法，这是合成各种十字花科代谢物所必需的起始材料，起始于容易获得的1H NMR溶剂[2H5]硝基苯（99%氘代）。然后使用在指定位置上99%氘代的[4,5,6,7-2H4]吲哚来合成[4′,5′,6′,7′-2H4]吲哚-3-乙酰肟、[4′,5′,6′,7′-2H4]1-甲氧基吲哚-3-乙酰肟、[1″,1″,1″,4′,5′,6′,7′-2H7]1-甲氧基吲哚-3-乙酰肟、[4′,5′,6′,7′-2H4]1-甲氧基油菜素内酯和[3,3,3,4′,5′,6′,7′-2H7]1-甲氧基油菜素内酯。版权所有 © 2005 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1028

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.