methyl 1-methoxyindole-3-carboxylate | 18377-50-9

• 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: methyl 1-methoxyindole-3-carboxylate
• 英文别名: N-methoxy-3-methoxycarbonyl-indole；(+/-)-phytoalexin；1-methoxy-indole-3-carboxylic acid methyl ester；Methyl 1-methoxy-1H-indole-3-carboxylate
• CAS: 18377-50-9
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: JAAYVMHPQAMBJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  methyl 1-methoxyindole-3-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 以0.7 g的产率得到1-甲氧基吲哚-3-羧酸
  参考文献：
  名称：

  Acheson, R. Morrin; Aldridge, Graham N.; Choi, Michael C. K., Journal of Chemical Research, Miniprint, 1984, # 4, p. 1301 - 1319

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲氧基-1H-吲哚-3-甲醛 在 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 以 甲醇 、 乙醚 、 叔丁醇 为溶剂， 反应 42.0h， 生成 methyl 1-methoxyindole-3-carboxylate
  参考文献：
  名称：

  Syntheses of Wasabi Phytoalexin (Methyl 1-Methoxyindole-3-carboxylate) and Its 5-Iodo Derivative, and Their Nucleophilic Substitution Reactions

  摘要：

  A simple synthetic method for methyl 1-methoxyindole-3-carboxylate, a phytoalexin isolated from Wasabia japonica, syn. Eutrema wasabi, and its 5-iodo derivative is reported. They underwent nucleophilic substitution reactions selectively at the 2-position.

  DOI：

  10.3987/com-00-s(i)12

文献信息

• Efficient Total Syntheses of Phytoalexin and (±)-Paniculidine B and C Based on the Novel Methodology for the Preparation of 1-Methoxyindoles
  作者：N. Selvakumar、G. Govinda Rajulu

  DOI：10.1021/jo040134l

  日期：2004.6.1

  2-unsubstituted-1-methoxyindoles, based on our methodology for the synthesis of 1-methoxyindoles, is reported. This synthesis renders accessibility to a variety of natural products possessing the said skeleton. A direct synthesis of phytoalexin (1), (±)-paniculidine B (2), and (±)-paniculidine C (3) is disclosed based on the methodology. The synthesis of paniculidine B (2) has been achieved from aldehyde 10 in only two

  据报道，基于我们合成1-甲氧基吲哚的方法，制备2-未取代的1-甲氧基吲哚的一般路线。该合成使具有所述骨架的多种天然产物可及。基于该方法公开了植物抗毒素（1），（±）-潘尼古丁B（2）和（±）-潘尼古丁C（3）的直接合成。潘尼古丁B（2）的合成仅由醛10分两步即可实现，产率为88％，而由使用我们较早方法获得的甲氧基吲哚化合物8分五步即可实现。
• Phytoalexin accumulation and antifungal compounds from the crucifer wasabi
  作者：M.Soledade C Pedras、John L Sorensen

  DOI：10.1016/s0031-9422(98)00424-5

  日期：1998.12

  Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm.] were isolated and their chemical structures determined. In addition, the chemical structure and synthesis of the first wasabi phytoalexin, methyl 1-methoxyindole-3-carboxylate, as well as its antifungal activity towards isolates of P. lingam and P. wasabiae were established.

  摘要 芥末 ( Wasabia japonica, syn. Eutrema wasabi ) 产生的组成型抗真菌代谢物，是一种对黑腿真菌 [ Leptosphaeria maculans (Desm.) Ces. 的毒力分离株具有抗性的植物。et de Not., 无性阶段 Phoma lingam (Tode ex Fr.) Desm.] 被分离出来并确定了它们的化学结构。此外，确定了第一个芥末植物抗毒素的化学结构和合成，即 1-甲氧基吲哚-3-羧酸甲酯，以及其对 P. lingam 和 P. wasabiae 的分离物的抗真菌活性。
• Efficient Synthesis of <i>N</i>-Methoxyindoles via Alkylative Cycloaddition of Nitrosoarenes with Alkynes
  作者：Andrea Penoni、Giovanni Palmisano、Gianluigi Broggini、Ayako Kadowaki、Kenneth M. Nicholas

  DOI：10.1021/jo051609r

  日期：2006.1.1

  N-Methoxyindoles are produced in moderate to excellent yields from the reaction between nitrosoarenes and alkynes in the presence of K2CO3/(CH3)2SO4. Terminal alkynes with conjugating substituents afford 3-substituted N-methoxyindoles exclusively. The analogous reactions with methyl propiolate provide a one-step preparation of phytoalexin analogues from Wasabi.

  在K 2 CO 3 /（CH 3）2 SO 4的存在下，亚硝基芳烃与炔烃之间的反应可中等至极高的产率生产N-甲氧基吲哚。具有共轭取代基的末端炔烃仅提供3-取代的N-甲氧基吲哚。与丙酸甲酯的类似反应提供了从芥末中一步制备植物抗毒素新类似物的方法。
• Two concise total syntheses of the wasabi phytoalexin methyl 1-methoxyindole-3-carboxylate
  作者：Bing Li、John D. Williams、Norton P. Peet

  DOI：10.1016/j.tetlet.2013.04.009

  日期：2013.6

  intermediate. Methyl 2-(2-nitrophenyl)acrylate (2) was directly converted into phytoalexin 1 using modified Cadogan–Sundberg indole synthesis conditions with trimethyl phosphite. Acrylate 2 also underwent reductive cyclization with stannous chloride to give methyl 1-hydroxyindole-3-carboxylate (3), which was methylated to produce phytoalexin 1.

  已开发出使用相同关键中间体的植物新毒素1-甲氧基吲哚-3-羧酸甲酯（1）的两种新合成方法。在亚磷酸三甲酯修饰的Cadogan-Sundberg吲哚合成条件下，将2-（2-硝基苯基）丙烯酸甲酯（2）直接转化为植物抗毒素1。丙烯酸酯2还经历了氯化亚锡的还原环化作用，得到了1-羟基吲哚-3-羧酸甲酯（3），该甲酯被甲基化生成了植物抗毒素1。
• PESTICIDAL COMPOSITION COMPRISING INDOLE DERIVATES
  申请人：Bednarek Pawel

  公开号：US20090028796A1

  公开（公告）日：2009-01-29

  The present invention is directed to pesticidal compositions comprising indole derivatives. These indole derivatives are especially active against phytopathogenic fungi. Furthermore, the invention relates to the use of indole derivatives for the production of pesticides and the use of the compositions according to the invention as pesticides. The present invention is also directed to a process for producing a pesticidal composition and to pesticidal compositions prepared by this process. In addition, the invention relates to a process for preventing or combating pests and to a process for protecting plants against pests, especially against phytopathogenic fungi. Further, the invention is directed to plants or seeds as well as objects or materials which have been protected against pests by treatment with a composition according to the invention. Further, the invention is directed to a method for identifying a substance having pesticidal activity. Further, the invention is directed to a method of identifying the mode of action of and/or of providing binding proteins for a pesticidal compound of the present invention. Finally, the invention is directed to a method for diagnosing pest infection of a plant and to the use of a pesticidal compound of the present invention as diagnostic markers.

  本发明涉及包含吲哚衍生物的杀虫组合物。这些吲哚衍生物特别对植物病原真菌具有活性。此外，本发明涉及使用吲哚衍生物制备杀虫剂以及使用本发明中的组合物作为杀虫剂。本发明还涉及制备杀虫组合物的过程以及通过该过程制备的杀虫组合物。此外，本发明还涉及预防或对抗害虫的过程以及保护植物免受害虫，特别是植物病原真菌的过程。此外，本发明还涉及经过本发明中的组合物处理后受到保护的植物或种子以及物体或材料。本发明还涉及识别具有杀虫活性的物质的方法。此外，本发明还涉及识别本发明中杀虫化合物的作用方式和/或提供结合蛋白的方法。最后，本发明涉及诊断植物害虫感染的方法以及使用本发明中的杀虫化合物作为诊断标记的方法。