N-isopropoxy-acetimidic acid ethyl ester | 18498-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-isopropoxy-acetimidic acid ethyl ester
• 英文别名: N-isopropoxy-acetimidic acid ethyl ester
• CAS: 18498-62-9
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: CIQFUMKVLASIKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-isopropoxy-acetimidic acid ethyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 isopropoxyamine
  参考文献：
  名称：

  Hydroxylamine derivatives

  摘要：

  DOI：

  10.1007/bf00906825
• 作为产物：
  描述：

  乙酰羟肟酸乙酯 、 甲磺酸异丙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 N-isopropoxy-acetimidic acid ethyl ester
  参考文献：
  名称：

  Novel hydroxylamine-containing analogues of 1-guanidino-7-aminoheptane (GC7), an effective inhibitor of deoxyhypusine synthase

  摘要：

  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.

  DOI：

  10.1134/s1068162016040099

文献信息

• Novel convenient synthesis of biologically active esters of hydroxylamine
  作者：Maxim A. Khomutov、Swati Mandal、Janne Weisell、Neiha Saxena、Alina R. Simonian、Jouko Vepsalainen、Rentala Madhubala、Sergey N. Kochetkov

  DOI：10.1007/s00726-009-0410-0

  日期：2010.2

  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.