di-tert-butyl 1,2-bis(2-(5-methoxy-1-tosyl-indol-3-yl)ethyl)hydrazine-1,2-dicarboxylate | 1453190-46-9

• 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: di-tert-butyl 1,2-bis(2-(5-methoxy-1-tosyl-indol-3-yl)ethyl)hydrazine-1,2-dicarboxylate
• 英文别名: tert-butyl N-[2-[5-methoxy-1-(4-methylphenyl)sulfonylindol-3-yl]ethyl]-N-[2-[5-methoxy-1-(4-methylphenyl)sulfonylindol-3-yl]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]carbamate
• CAS: 1453190-46-9
• 化学式: C₄₆H₅₄N₄O₁₀S₂
• 分子量: 887.088
• InChiKey: KTTBMPJXQSLDOC-UHFFFAOYSA-N

物化性质

• 沸点：
  945.9±75.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  62
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 1,2-bis(2-(5-methoxy-1-tosyl-indol-3-yl)ethyl)hydrazine-1,2-dicarboxylate 在 甲醇 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成
  参考文献：
  名称：

  Bidirectional synthesis of montamine analogs

  摘要：

  Reported herein is a bidirectional synthesis of symmetric N,N'-diacyl hydrazide compounds closely resembling the alkaloid natural product montamine. In the process, di-tert-butyl hydrazine-1,2-dicarboxylate was smoothly dialkylated with alkyl halides, then Boc deprotected and acylated with an acetate-protected acid chloride derived from ferulic acid. After acetate removal, simple montamine analogs were obtained in excellent overall yields. Fischer indole synthesis with 4-methoxyphenylhydrazine hydrochloride and dihydrofuran provided 5-methoxytryptophol, which was then elaborated to the 1,2-bis(5-methoxyindo1-3-yl)hydrazide structure bearing the substitution pattern found in montamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.134
• 作为产物：
  描述：

  5-甲氧基吲哚-3-乙醇 在 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 139.17h， 生成 di-tert-butyl 1,2-bis(2-(5-methoxy-1-tosyl-indol-3-yl)ethyl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Bidirectional synthesis of montamine analogs

  摘要：

  Reported herein is a bidirectional synthesis of symmetric N,N'-diacyl hydrazide compounds closely resembling the alkaloid natural product montamine. In the process, di-tert-butyl hydrazine-1,2-dicarboxylate was smoothly dialkylated with alkyl halides, then Boc deprotected and acylated with an acetate-protected acid chloride derived from ferulic acid. After acetate removal, simple montamine analogs were obtained in excellent overall yields. Fischer indole synthesis with 4-methoxyphenylhydrazine hydrochloride and dihydrofuran provided 5-methoxytryptophol, which was then elaborated to the 1,2-bis(5-methoxyindo1-3-yl)hydrazide structure bearing the substitution pattern found in montamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.134