ethyl N-butoxyethanimidate | 60302-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl N-butoxyethanimidate
• CAS: 60302-19-4
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: NPMNCQWZURDKAM-UHFFFAOYSA-N

物化性质

• 沸点：
  91-91.5 °C(Press: 47 Torr)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-butoxyethanimidate 在 盐酸 、 水 作用下， 以 异丙醇 为溶剂， 以97%的产率得到O-丁基羟胺盐酸盐
  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
• 作为产物：
  描述：

  甲磺酸正丁酯 、 sodium ethyl N-hydroxyacetimidate 以78%的产率得到ethyl N-butoxyethanimidate
  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

文献信息

• Synthesis and some properties of aminooxyalkylcelluloses
  作者：A. A. Nedospasov、R. M. Khomutov

  DOI：10.1007/bf00922002

  日期：1976.5
• Novel hydroxylamine-containing analogues of 1-guanidino-7-aminoheptane (GC7), an effective inhibitor of deoxyhypusine synthase
  作者：M. A. Khomutov、A. R. Simonian、J. Weisell、J. Vepsalainen、S. N. Kochetkov、A. R. Khomutov

  DOI：10.1134/s1068162016040099

  日期：2016.7

  Earlier unknown hydroxylamine-containing analogues of 1-guanidino-7-aminohepane (GC7) containing the free aminooxy group (1-aminooxy-6-guanidinohexane), bis-guanyl derivatives of 1-aminooxy-6-aminohexane, and 1-aminooxy-5-aminopentane, and mono-guanidinooxy analogue (1-guanidinooxy-6-aminohexane) were synthesized in high overall yields from commercially available 5-(Boc-amino)1-pentanol and 6-(Boc-amino)-1-hexanol. It was demonstrated that 1,3-di-Boc-2-(trifluoromethylsulfonyl)guanidine is able to specifically amidinate the amino group in the presence of the free aminooxy group. The application of newly synthesized GC7 analogues for the investigation of the peculiarities of their interaction with the active site of deoxyhypusine synthase was discussed.