(E)-tert-butyl 2-(2-methoxyacetyl)-1-(tetradec-1-en-1-yl)hydrazinecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-tert-butyl 2-(2-methoxyacetyl)-1-(tetradec-1-en-1-yl)hydrazinecarboxylate
• 英文别名: tert-butyl (E)-2-(2-methoxyacetyl)-1-(tetradec-1-en-1-yl)hydrazine-1-carboxylate；tert-butyl N-[(2-methoxyacetyl)amino]-N-[(E)-tetradec-1-enyl]carbamate
• 化学式: C₂₂H₄₂N₂O₄
• 分子量: 398.586
• InChiKey: HGPVYEZKMSWGEP-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  tert-butyl (E)-1-(tetradec-1-en-1-yl)hydrazine-1-carboxylate 、 甲氧基乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以62%的产率得到(E)-tert-butyl 2-(2-methoxyacetyl)-1-(tetradec-1-en-1-yl)hydrazinecarboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of hydrazidomycin analogues

  摘要：

  Hydrazidomycin A is an unusual secondary metabolite of Streptomyces atratus that features a rare enehydrazide core. To learn more about structure-activity relationships of the reported cytotoxic and antiproliferative agent several synthetic routes were explored to synthesize a variety of hydrazidomycin derivatives. Specifically, the size of the side chains, the nature of the double bond and the polar head group were altered. Overall, fourteen analogues were tested for their cytotoxic and antiproliferative effects. Re-examination of synthetic hydrazidomycin A suggests that the antiproliferative activity is attributed to a yet unknown compound that results from degradation or rearrangement. Several of the less complex analogues, however, show antiproliferative activities against individual cancer cell lines and turned out to be more potent than hydrazidomycin A. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.033

文献信息

• Total Synthesis of the Cytotoxic Enehydrazide Natural Products Hydrazidomycins A and B by a Carbazate Addition/Peterson Olefination Approach
  作者：Ramsay E. Beveridge、Robert A. Batey

  DOI：10.1021/ol401275f

  日期：2013.6.21

  The first total syntheses of two natural antitumor enehydrazide compounds (hydrazidomycins A and B) and a related positional isomer of hydrazidomycin B (elaiomycin B) have been accomplished in a rapid and stereocontrolled fashion using a Peterson elimination approach. A regioselective silyl epoxide ring opening reaction with Boc-carbazate followed by base-mediated Peterson siloxide elimination stereospecifically

  两种天然抗肿瘤烯乙肼化合物（肼霉素A和B）和肼霉素B（伊莱霉素B）的相关位置异构体的第一批总合成已使用Peterson消除法以快速和立体控制的方式完成。与Boc- carbazate的区域选择性甲硅烷基环氧化物开环反应，然后通过碱介导的Peterson硅氧化物消除，立体定向地安装了关键的Z-乙酰肼功能。Boc-氨基甲酸酯的使用允许酰肼氮的差异官能化。