S-methyl [(1-methyl-2-sulfanyl-1H-indolyl-3)methyl]carbamothioate | 1418290-93-3

• 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: S-methyl [(1-methyl-2-sulfanyl-1H-indolyl-3)methyl]carbamothioate
• 英文别名: S-methyl N-[(1-methyl-2-sulfanylindol-3-yl)methyl]carbamothioate
• CAS: 1418290-93-3
• 化学式: C₁₂H₁₄N₂OS₂
• 分子量: 266.388
• InChiKey: YIHLIYCUJKABLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-methyl [(1-methyl-2-sulfanyl-1H-indolyl-3)methyl]carbamothioate 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.08h， 以63%的产率得到S-methyl [(1-methyl-2-sulfanylmethyl-1Hindolyl-3)methyl]carbamothioate
  参考文献：
  名称：

  Unprecedented spirocyclization of 3-methyleneindoline-2-thiones during hydrolysis of the phytoalexin cyclobrassinin

  摘要：

  The phytoalexin cyclobrassinin is a plant defense that has additional importance since it inhibits brassinin hydrolase, a phytoalexin detoxifying enzyme produced by the plant pathogen Alternaria brassicicola. Hence, the 1,3-thiazino[6,5-b] indole scaffold of cyclobrassinin has great application as a lead structure to design potential inhibitors of brassinin detoxification. For this reason, it is necessary to determine whether A. brassicicola is able to transform cyclobrassinin. During this work new reactions of 1,3-thiazino[6,5-b] indoles and indoline-2-thiones and their unique [4+2] cycloaddition products were discovered and characterized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.042
• 作为产物：
  描述：

  1-methylcyclobrassinin 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以35%的产率得到S-methyl [(1-methyl-2-sulfanyl-1H-indolyl-3)methyl]carbamothioate
  参考文献：
  名称：

  Unprecedented spirocyclization of 3-methyleneindoline-2-thiones during hydrolysis of the phytoalexin cyclobrassinin

  摘要：

  The phytoalexin cyclobrassinin is a plant defense that has additional importance since it inhibits brassinin hydrolase, a phytoalexin detoxifying enzyme produced by the plant pathogen Alternaria brassicicola. Hence, the 1,3-thiazino[6,5-b] indole scaffold of cyclobrassinin has great application as a lead structure to design potential inhibitors of brassinin detoxification. For this reason, it is necessary to determine whether A. brassicicola is able to transform cyclobrassinin. During this work new reactions of 1,3-thiazino[6,5-b] indoles and indoline-2-thiones and their unique [4+2] cycloaddition products were discovered and characterized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.042

文献信息

• Unprecedented spirocyclization of 3-methyleneindoline-2-thiones during hydrolysis of the phytoalexin cyclobrassinin
  作者：M. Soledade C. Pedras、Abbas Abdoli、Paulos B. Chumala、Pijus Saha、Gabriele Schatte

  DOI：10.1016/j.bmcl.2012.11.042

  日期：2013.1

  The phytoalexin cyclobrassinin is a plant defense that has additional importance since it inhibits brassinin hydrolase, a phytoalexin detoxifying enzyme produced by the plant pathogen Alternaria brassicicola. Hence, the 1,3-thiazino[6,5-b] indole scaffold of cyclobrassinin has great application as a lead structure to design potential inhibitors of brassinin detoxification. For this reason, it is necessary to determine whether A. brassicicola is able to transform cyclobrassinin. During this work new reactions of 1,3-thiazino[6,5-b] indoles and indoline-2-thiones and their unique [4+2] cycloaddition products were discovered and characterized. (C) 2012 Elsevier Ltd. All rights reserved.