1-甲氧基吲哚-2-甲醛 | 3289-87-0

• 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
• 中文名称: 1-甲氧基吲哚-2-甲醛
• 英文名称: 1-methoxyindole-2-carboxaldehyde
• 英文别名: 1-Methoxyindole-2-carbaldehyde
• CAS: 3289-87-0
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: KNTNZVQXPFYQIY-UHFFFAOYSA-N

物化性质

• 沸点：
  314.9±34.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲氧基吲哚-2-甲醛 在 吡啶 、 titanium(III) chloride 、 盐酸羟胺 、 ammonium acetate 、 sodium cyanoborohydride 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 17.66h， 生成 1-methoxyisobrassinin
  参考文献：
  名称：

  前所未有的化学结构和仿生合成的芥蓝素，一种来自野生十字花科植物金缕梅的植物抗毒素。

  摘要：

  描述了芥蓝素的分离，结构测定，总合成和抗真菌活性。芥蓝素是野生十字花科狗芥菜产生的一种新型植物抗毒素。芥蓝素是一种结构独特的植物生物碱，代表螺[2H-吲哚-2,5'（4'H）-噻唑] -3-one的第一个实例，可能源自C-3-C-2碳迁移在3-取代的吲哚基核中。

  DOI：

  10.1039/b515331j
• 作为产物：
  描述：

  1-羟基吲哚 在 正丁基锂 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 1-甲氧基吲哚-2-甲醛
  参考文献：
  名称：

  Kawasaki, Toshiya; Kodama, Atsushi; Nishida, Tokiko, Heterocycles, 1991, vol. 32, # 2, p. 221 - 227

  摘要：

  DOI：

文献信息

• Regiodivergent Annulation of Alkynyl Indoles To Construct Spiro-pseudoindoxyl and Tetrahydro-β-carbolines
  作者：Yong-Qiang Zhang、Dao-Yong Zhu、Zhi-Wei Jiao、Bao-Sheng Li、Fu-Min Zhang、Yong-Qiang Tu、Zhigang Bi

  DOI：10.1021/ol201194n

  日期：2011.7.1

  Regiodivergent annulations of 3-phenoxy alkynyl indoles have been developed and tuned by protective groups through gold catalysis. With electron-donating protective groups, the substrate followed a C3-selective annulation and gave structurally interesting tetrahydro-β-carboline derivatives possessing potential bioactivity. Using electron-withdrawing protective groups, the substrate underwent a C2-selective

  已经开发了3-苯氧基炔基吲哚的区域发散环，并通过金催化通过保护基进行了调节。带有给电子保护基团的底物经过C3选择性环化，得到结构上令人感兴趣的具有潜在生物活性的四氢-β-咔啉衍生物。使用吸电子保护基团，底物经历了C2选择性环化，并提供了在天然吲哚生物碱中发现的结构上有用的螺-伪吲哚酚。值得注意的是，在C3选择性过程中发现了一个有趣且不寻常的苯氧基1，2-迁移。
• Yamada, Fumio; Fukui, Yoshikazu; Shinmyo, Daisuke, Heterocycles, 1993, vol. 35, # 1, p. 99 - 104
  作者：Yamada, Fumio、Fukui, Yoshikazu、Shinmyo, Daisuke、Somei, Masanori

  DOI：——

  日期：——
• The Chemistry of 1-Hydroxyindole Derivatives: Nucleophilic Substitution Reactions on Indole Nucleus
  作者：Masanori Somei、Toshiya Kawasaki、Yoshikazu Fukui、Fumio Yamada、Tetsuya Kobayashi、Harumi Aoyama、Daisuke Shinmyo

  DOI：10.3987/com-92-6140

  日期：——

  Nucleophilic substitution reactions were newly found to occur generally in the chemistry of 1-hydroxyindole derivatives. Its application to the synthesis of a phytoalexin, brassicanal A, is reported.
• Metabolism and Metabolites of Dithiocarbamates in the Plant Pathogenic Fungus Leptosphaeria maculans
  作者：M. Soledade C. Pedras、Vijay K. Sarma-Mamillapalle

  DOI：10.1021/jf302038a

  日期：2012.8.15

  Synthetic compounds containing a dithiocarbamate group are known to have a variety of biological effects and applications including antifungal, herbicidal, and insecticidal application. Leptosphaeria maculans is a fungal pathogen of crucifers able to detoxify efficiently the only plant natural product containing a dithiocarbamate group, the phytoalexin brassinin. To evaluate the effects of dithiocarbamates on L. maculans, a number of structurally diverse S-methyl dithiocarbamates containing indolyl, biphenyl, and benzimidazolyl moieties were synthesized, and their antifungal activities and metabolism by L. maculans were investigated. All dithiocarbamates were transformed by L. maculans through hydrolysis to the corresponding amines, which were less antifungal than the parent compounds. Two dithiocarbonates were shown to be much less antifungal than the corresponding dithiocarbamates. Results of this investigation indicate that S-methyl dithiocarbamates are not useful inhibitors of L. maculans and that their rates of transformation by L. maculans did not correlate with the antifungal activity of the particular compound.
• Lithiation of 1-Alkoxyindole Derivatives
  作者：Masanori Somei、Kyoko Nakagawa (Goto)、Tetsuya Kobayashi、Toshiya Kawasaki

  DOI：10.3987/com-18-s(t)77

  日期：——

  Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.