1-[[(4S,5S)-2,2-dimethyl-5-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]-1,3-dioxolan-4-yl]methyl]indole-3-carbonitrile | 147727-20-6

• 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-[[(4S,5S)-2,2-dimethyl-5-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]-1,3-dioxolan-4-yl]methyl]indole-3-carbonitrile
• CAS: 147727-20-6
• 化学式: C₁₉H₁₉N₃O₂S₂
• 分子量: 385.511
• InChiKey: MSCHYUWDZYFKSJ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  60.07
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-[[(4S,5S)-2,2-dimethyl-5-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]-1,3-dioxolan-4-yl]methyl]indole-3-carbonitrile 在 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 9.25h， 生成 (8S,9R,10R,14S)-12,12-dimethyl-11,13-dioxa-1-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2,4,6-triene-8-carbonitrile
  参考文献：
  名称：

  Intramolecular addition of a dioxolanyl radical to the indole nucleus: preparation of enantiomerically pure, oxygenated perhydro-3H-pyrrolo[1,2-a]indoles

  摘要：

  The cyclization of dioxolanyl radicals, which were generated by the Barton tartrate-derived thiohydroxamate ester (mixed anhydride) procedure, with an indole nucleus has been explored. The products derived from these reactions have been identified and their chemistry investigated with the goal of uncovering new entries into enantiomerically pure, mitomycin-like structures. Thus, the photolysis of 1-hydroxy-2-thiopyridone ester 8c and 1-hydroxy-4-methylthiazole-2(3H)-thione ester gd has been conducted with UV and visible light. The photochemistry of the products, namely, dimer 9, dihydroindole 12a, indole 11, and thiazole 13c, derived from the thiohydroxamate esters and putative intermediates 18a and 18b, was also explored.

  DOI：

  10.1021/jo00062a019
• 作为产物：
  描述：

  (4-methyl-2-sulfanylidene-1,3-thiazol-3-yl) (4R,5S)-5-[(3-cyanoindol-1-yl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 以5%的产率得到
  参考文献：
  名称：

  Ziegler Frederick E., Harran Patrick G., J. Org. Chem., 58 (1993) N 10, S 2768-2773

  摘要：

  DOI：