N-(isopropoxymethyl)-3-methylbutanamide | 156026-05-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(isopropoxymethyl)-3-methylbutanamide
• 英文别名: Butanamide, 3-methyl-N-[(1-methylethoxy)methyl]-；3-methyl-N-(propan-2-yloxymethyl)butanamide
• CAS: 156026-05-0
• 化学式: C₉H₁₉NO₂
• 分子量: 173.255
• InChiKey: QIAVNOYABNIBTK-UHFFFAOYSA-N

物化性质

• 沸点：
  281.1±23.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(isopropoxymethyl)-3-methylbutanamide 、 烯丙基三甲基硅烷 在 三氟化硼 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到N-(3-butenyl)-3-methylbutanamide
  参考文献：
  名称：

  Generation of N-acyl iminium ions from ionization-rearrangement reactions of N-triflyloxy amides

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)76872-9
• 作为产物：
  描述：

  N-hydroxy-N-methyl-3-methylbutanamide 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-(isopropoxymethyl)-3-methylbutanamide
  参考文献：
  名称：

  Generation of N-acyl iminium ions from ionization-rearrangement reactions of N-triflyloxy amides

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)76872-9

文献信息

• 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：——
• Hoffman Robert V., Nayyar Naresh K., Shankweiler Jean M., Klinekole Bruce+, Tetrahedron Lett, 35 (1994) N 20, S 3231-3234
  作者：Hoffman Robert V., Nayyar Naresh K., Shankweiler Jean M., Klinekole Bruce+

  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.
• 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.