2-methylsulfanyl-1H-indole-3-carbaldehyde | 113866-44-7

• 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: 2-methylsulfanyl-1H-indole-3-carbaldehyde
• 英文别名: 2-Methylthioindole-3-carbaldehyde；brassicanal A
• CAS: 113866-44-7
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: QSSMEVWVRIEBSR-UHFFFAOYSA-N

物化性质

• 熔点：
  233-234 °C
• 沸点：
  393.0±27.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  58.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylsulfanyl-1H-indole-3-carbaldehyde 在 sodium tetrahydroborate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-(hydroxymethyl)indole 2-methylsulfoxide
  参考文献：
  名称：

  Biotransformation of the Brassica Phytoalexin Brassicanal A by the Blackleg Fungus

  摘要：

  The biotransformation of the brassica phytoalexin brassicanal A by the blackleg fungus [Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm] was investigated. Three main biotransformation products were detected and isolated; their chemical structures were determined by spectroscopic methods and concomitant synthesis. Additionally, the antifungal activities of brassicanal A and its biotransformation products were compared. Overall, the biotransformation pathway suggests that the blackleg fungus has enzymes to carry out this biotransformation different from those involved in the biotransformation of the brassica phytoalexin brassinin.

  DOI：

  10.1021/jf960098u
• 作为产物：
  描述：

  1,3-二氢-2H-吲哚-2-硫酮 在 sodium hydride 作用下， 以 乙醚 为溶剂， 生成 2-methylsulfanyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  A convenient synthesis of the cruciferous phytoalexins brassicanal A and brassilexin by mimicry of a fungal detoxification pathway

  摘要：

  十字花科植物抗毒素brassilxin 3是由二氢吲哚-2-硫酮通过3-(氨基亚甲基)吲哚-2-硫酮2（植物抗毒素环芸苔素1解毒途径的代谢中间体）分四个步骤合成的；此外，植物抗毒素芸苔醛 A 8 是由 2-二氢吲哚硫酮分两步合成的。

  DOI：

  10.1039/a803485k

文献信息

• Strategies of Cruciferous Pathogenic Fungi:  Detoxification of the Phytoalexin Cyclobrassinin by Mimicry
  作者：M. Soledade C. Pedras、Francis I. Okanga

  DOI：10.1021/jf980854r

  日期：1999.3.1

  (Rhizoctonia solani Kuhn) and blackleg [Phoma lingam (Tode ex Fr.) Desm., asexual stage of Leptosphaeria maculans (Desm.) Ces. et de Not.] fungi is reported. It was established that R. solani metabolized and detoxified cyclobrassinin via the phytoalexin brassicanal A, which was further transformed into nontoxic products. Detoxification of cyclobrassinin in P. lingam avirulent isolate Unity occurred via

  致病性根腐烂菌（Rhizoctonia solani Kuhn）和黑腿病（Phoma lingam（Tode ex Fr.）Desm。，十字花科黄斑狼疮（Desm。）Ces的无性繁殖期，十字花科植物抗毒素环花青素的显着代谢。等]真菌的报道。已经确定，茄尼色单胞菌通过植物抗毒素黄铜素A代谢和解毒了环孢素，并将其进一步转化为无毒产品。灵芝P. lingam无毒分离株中环花青素的解毒通过植物抗毒素黄铜素而发生，而灵芝P.毒性分离株BJ 125中的解毒则通过植物抗毒素二氧西ass素发生。描述了这三种明显不同途径的中间体的结构确定中涉及的化学及其抗真菌活性。此外，据报道，通过模仿真菌的生物转化途径，高效合成了植物抗毒素类芸苔素A和黄铜抗毒素。讨论了这些前所未有的转变的含义。
• Syntheses of Wasabi Phytoalexin (Methyl 1-Methoxyindole-3-carboxylate) and Its 5-Iodo Derivative, and Their Nucleophilic Substitution Reactions
  作者：Masanori Somei、Asuka Tanimoto、Hitomi Orita、Fumio Yamada、Toshiharu Ohta

  DOI：10.3987/com-00-s(i)12

  日期：——

  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.
• Nucleophilic Substitution Reaction of 1-Methoxyindole-3-carbaldehyde
  作者：Masanori Somei、Fumio Yamada、Daisuke Shinmyo、Masahiro Nakajou

  DOI：10.3987/com-12-s(n)41

  日期：——

  1-Methoxyindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-position with various types of nucleophiles providing 2-substituted indole-3-carbaldehydes.
• 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.
• Tomchin; Marysheva, Russian Journal of Organic Chemistry, 1999, vol. 35, # 7, p. 1060 - 1068
  作者：Tomchin、Marysheva

  DOI：——

  日期：——