N-[(3-methyloxetan-3-yl)methyl]-N-propylbutanamide | 266312-00-9

• 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-[(3-methyloxetan-3-yl)methyl]-N-propylbutanamide
• CAS: 266312-00-9
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: DYVYQXABNSCKMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(3-methyloxetan-3-yl)methyl]-N-propylbutanamide 在 三氟化硼乙醚 作用下， 以 氯苯 为溶剂， 生成 4-Methyl-1,7-dipropyl-2,6-dioxa-7-azabicyclo[2.2.2]octane
  参考文献：
  名称：

  Isomerization of cyclic ethers having a carbonyl functional group: new entries into different heterocyclic compounds

  摘要：

  Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00701-9
• 作为产物：
  描述：

  1,1,1-三(羟甲基)乙烷 在 氢氧化钾 、 sodium hydroxide 、 四丁基硫酸氢铵 、 potassium carbonate 、 一水合肼 、 碳酸二乙酯 作用下， 反应 2.0h， 生成 N-[(3-methyloxetan-3-yl)methyl]-N-propylbutanamide
  参考文献：
  名称：

  氧杂环丁烷酰胺双异构化为氮杂环丁烷酯，具有环的膨胀和收缩

  摘要：

  DOI：

  10.1021/jo991888g

文献信息

• Double Isomerization of Oxetane Amides to Azetidine Esters with Ring Expansion and Contraction
  作者：Shigeyoshi Kanoh、Tomonari Nishimura、Yukiko Kita、Hiroshi Ogawa、Masatoshi Motoi、Masako Takani、Toshiyuki Tanaka

  DOI：10.1021/jo991888g

  日期：2000.4.1
• Isomerization of cyclic ethers having a carbonyl functional group: new entries into different heterocyclic compounds
  作者：Shigeyoshi Kanoh、Masashi Naka、Tomonari Nishimura、Masatoshi Motoi

  DOI：10.1016/s0040-4020(02)00701-9

  日期：2002.8

  Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.