6-(1-ethoxyethylideneamino-oxy)-1-hexanol | 1226995-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(1-ethoxyethylideneamino-oxy)-1-hexanol
• CAS: 1226995-31-8
• 化学式: C₁₀H₂₁NO₃
• 分子量: 203.282
• InChiKey: VPSPKOYIAJRMDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  14.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  51.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(1-ethoxyethylideneamino-oxy)-1-hexanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 生成 ethyl N-((6-((methylsulfonyl)oxy)hexyl)oxy)acetimidate
  参考文献：
  名称：

  Novel convenient synthesis of biologically active esters of hydroxylamine

  摘要：

  Alkylation of ethyl N-hydroxyacetimidate with readily available methanesulfonates of functionally substituted alcohols and subsequent deprotection of aminooxy group is a novel and convenient method to prepare functionally substituted esters of hydroxylamine with high overall yield. This approach is a good alternative to well-known reaction of N-hydroxyphthalimide with alcohols under the Mitsunobu conditions. The properties of ethoxyethylidene protection of aminooxy group on the contrary to that of N-alkoxyphthalimide group allow to perform a wide spectra of the transformations in the radical of N-protected hydroxylamine derivatives. This is essential for synthetic strategies consisting in the introduction of N-protected aminooxy group at one of the first steps of synthesis and subsequent transformations of the radical.The inhibitory effect of one of the newly synthesized compound, 1-guanidinooxy-3-aminopropane (GAPA), was compared with that of well-known inhibitors of ornithine decarboxylase namely, alpha-difluoromethylornithine (DFMO) and 1-aminooxy-3-aminopropane (APA) on Leishmania donovani, a protozoan parasite that causes visceral leishmaniasis. GAPA, on the contrary with APA and DFMO, in micromolar concentrations, inhibited the growth of both amastigotes and promastigotes of sodium antimony gluconate-resistant forms of L. donovani.

  DOI：

  10.1007/s00726-009-0410-0