1'-methylindol-3'-ylacetaldoxime | 1190220-42-8

• 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'-methylindol-3'-ylacetaldoxime
• CAS: 1190220-42-8
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: NWDGTHZMXJIAPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.52
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1'-methylindol-3'-ylacetaldoxime 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 生成 (1-甲基-1H-吲哚-3-基)甲胺
  参考文献：
  名称：

  1H-Pyrido[4,3-b] 吲哚和 Spiro[indoline-3,3'-pyridine] 衍生物的 Au(I) 催化取代控制合成的量子力学预测和实验验证

  摘要：

  应用密度泛函理论计算预测了金（I）催化的吲哚底物与 1,6-烯炔的环化异构化途径，这与随后的实验结果一致。取代控制合成导致以可调方式形成 1 H-吡啶并[4,3- b ]吲哚和螺[吲哚啉-3,3'-吡啶]衍生物。该反应具有良好的官能团耐受性，并根据计算和实验结果提出了可能的机理。

  DOI：

  10.1021/acs.joc.2c03104
• 作为产物：
  描述：

  2-(1-methyl-1H-indol-3-yl)acetaldehyde 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 以73.3 mg的产率得到1'-methylindol-3'-ylacetaldoxime
  参考文献：
  名称：

  The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: De novo incorporation of deuterated tryptophans and quasi-natural compounds

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2009.05.015

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.
• Quantum Mechanical Prediction and Experimental Verification of Au(I)-Catalyzed Substitution-Controlled Syntheses of 1<i>H</i>-Pyrido[4,3-<i>b</i>]indole and Spiro[indoline-3,3′-pyridine] Derivatives
  作者：Jiang Zhu、Jiaji Li、Lianjie Zhang、Shitao Sun、Zhaobo Wang、Xiang Li、Lu Yang、Maosheng Cheng、Bin Lin、Yongxiang Liu

  DOI：10.1021/acs.joc.2c03104

  日期：2023.5.5

  functional theory calculations were applied to predict the pathways of gold(I)-catalyzed cycloisomerization of the indole substrates with 1,6-enynes, which were consistent with the ensuing experimental results. The substitution-controlled synthesis led to the formation of 1H-pyrido[4,3-b]indole and spiro[indoline-3,3′-pyridine] derivatives in a tunable way. The reactions had good functional group tolerances

  应用密度泛函理论计算预测了金（I）催化的吲哚底物与 1,6-烯炔的环化异构化途径，这与随后的实验结果一致。取代控制合成导致以可调方式形成 1 H-吡啶并[4,3- b ]吲哚和螺[吲哚啉-3,3'-吡啶]衍生物。该反应具有良好的官能团耐受性，并根据计算和实验结果提出了可能的机理。