di-tert-butyl 1,2-dibutylhydrazine-1,2-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: di-tert-butyl 1,2-dibutylhydrazine-1,2-dicarboxylate
• 英文别名: tert-butyl N-butyl-N-[butyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]carbamate
• 化学式: C₁₈H₃₆N₂O₄
• 分子量: 344.495
• InChiKey: ZEBDLTYJIASQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 1,2-dibutylhydrazine-1,2-dicarboxylate 在 甲醇 、 乙酰氯 作用下， 反应 18.0h， 生成 1,2-Dibutylhydrazine;hydrochloride
  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：

  正溴丁烷 、 二叔丁基叠氮草酸 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以70%的产率得到di-tert-butyl 1,2-dibutylhydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  轻松合成单，双和三取代的α-支化肼

  摘要：

  研究了肼合1,2-二羧酸二叔丁酯的烷基化方法。发现在温和的条件下以良好至优异的产率获得了单取代或二取代的肼衍生物。此外，显示出通过加热选择性地除去了二取代衍生物的两个Boc基团之一，从而产生了三取代肼的前体。

  DOI：

  10.1021/jo0525783

文献信息

• Facile Synthesis of Mono-, Di-, and Trisubstituted Alpha-Unbranched Hydrazines
  作者：Lars K. Rasmussen

  DOI：10.1021/jo0525783

  日期：2006.4.1

  2-dicarboxylate were investigated. It was found that under mild conditions mono- or di-substituted hydrazine derivatives were obtained in good to excellent yield. Furthermore, it was shown that one of the two Boc-groups of the disubstituted derivatives was selectively removed by heating, leading to precursors for trisubstituted hydrazines.

  研究了肼合1,2-二羧酸二叔丁酯的烷基化方法。发现在温和的条件下以良好至优异的产率获得了单取代或二取代的肼衍生物。此外，显示出通过加热选择性地除去了二取代衍生物的两个Boc基团之一，从而产生了三取代肼的前体。
• Bidirectional synthesis of montamine analogs
  作者：Melanie B. Freitas、Kelly A. Simollardes、Caroline M. Rufo、Chantel N. McLellan、Gabrielle J. Dugas、Leslie E. Lupien、Elizabeth A. Colby Davie

  DOI：10.1016/j.tetlet.2013.07.134

  日期：2013.10

  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.