N-hydroxy-N-methyl-2-carbetoxyethanamide | 156025-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-hydroxy-N-methyl-2-carbetoxyethanamide
• 英文别名: N-Hydroxy-2-carbethoxy-N-methylacetamide；Ethyl 3-(hydroxy-methylamino)-3-oxopropanoate；ethyl 3-[hydroxy(methyl)amino]-3-oxopropanoate
• CAS: 156025-63-7
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: LXVGROQHCACGAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-hydroxy-N-methyl-2-carbetoxyethanamide 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 N-(isopropoxymethyl)-1-carbetoxyethanamide
  参考文献：
  名称：

  A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides

  摘要：

  A series of hydroxamic acids were converted to N-triflyloxy amides which were heated in 2-propanol to give N-(1-isopropoxyalkyl) amides in high yields. The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, as well as in the 1-isopropoxyalkyl group. N-Alkylation of secondary N-(1-isopropoxyalkyl) amides can be used for converting them to tertiary N-(1-isopropoxyalkyl) amides. N-Acyliminium ions of wide structural diversity can be generated easily from N-(1-isopropoxyalkyl) amides available by this methodology.

  DOI：

  10.1021/jo00092a007
• 作为产物：
  描述：

  N-甲基羟胺盐酸盐 、 氯甲酰乙酸乙酯 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以52%的产率得到N-hydroxy-N-methyl-2-carbetoxyethanamide
  参考文献：
  名称：

  N-烷基-O-酰基异羟肟酸的碱介导反应：3-oxo-2,3-dihydro-4-isoxazole羧酸酯衍生物的合成

  摘要：

  用磷腈超强碱P-2- t - Bu 7处理丙二酰衍生的O-酰基异羟肟酸衍生物10a - h，得到2,3-二氢-4-异恶唑羧酸酯衍生物11a - h。反应的速率和产率取决于O-酰基取代基。

  DOI：

  10.1016/j.tetlet.2003.08.098

文献信息

• Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity
  作者：Witold Przychodzeń

  DOI：10.1002/hc.20259

  日期：——

  To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic α-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two

  为了探索异羟肟酸 (HA) 直接硫化的一般性和范围，研究了各种结构不同的 HA 与劳森试剂的反应。当 HA 具有庞大的酰基和/或 N-取代基、酸性 α-氢原子或 N-苯环时，硫代异羟肟酸 (THA) 的产率很低。THA 产量与 Brown sigma 参数相关。还测量了两个后续过程 k 和 k 的相对速率。还发现了 N-异丙基苯并硫代异羟肟酸的次甲基质子化学位移的相关性。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:676–684, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20259
• Generation of N-acyl iminium ions from ionization-rearrangement reactions of N-triflyloxy amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Jean M. Shankweiler、Bruce W. Klinekole

  DOI：10.1016/s0040-4039(00)76872-9

  日期：1994.5

  N-Triflyloxy amides undergo ionization in refluxing isopropanol to give N-acyliminium ions which can be trapped by addition of allyltrimethylsilane to the reaction mixture. Alternatively they can be converted to N-(isopropoxy)alkyl amides and then back to N-acyliminium ions under a variety of conditions.
• Origins of Regioselectivity in the Reactions of .alpha.-Lactams with Nucleophiles
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00118a032

  日期：1995.6

  Regioselectivity in the reaction of alpha-lactams with nucleophiles results from two competing steps. Nucleophilic addition to the carbonyl group of the alpha-lactam, which yields rearranged, acyl-substituted products, is dependent on the nucleophilicity and the concentration of the nucleophile. Ring opening of the alpha-lactam to an ion pair intermediate, which gives nucleophile incorporation at C-2, is dependent on electronic effects of substituents at C-2. Groups which can stabilize positive charge at C-2 speed up ion pair formation, whereas electron-withdrawing groups slow the ring opening and give more carbonyl addition product. These factors are used to control the regioselectivity and produce a series of unsymmetric urea peptide mimetics in high yields and with complete regiochemical control.
• Hoffman Robert V., Nayyar Naresh K., J. Org. Chem, 59 (1994) N 13, S 3530-3539
  作者：Hoffman Robert V., Nayyar Naresh K.

  DOI：——

  日期：——
• A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides
  作者：Robert V. Hoffman、Naresh K. Nayyar

  DOI：10.1021/jo00092a007

  日期：1994.7

  A series of hydroxamic acids were converted to N-triflyloxy amides which were heated in 2-propanol to give N-(1-isopropoxyalkyl) amides in high yields. The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, as well as in the 1-isopropoxyalkyl group. N-Alkylation of secondary N-(1-isopropoxyalkyl) amides can be used for converting them to tertiary N-(1-isopropoxyalkyl) amides. N-Acyliminium ions of wide structural diversity can be generated easily from N-(1-isopropoxyalkyl) amides available by this methodology.