5-hydroxymethyl-5-methyl-5,6-dihydro-4H-1,3-oxazine | 202871-75-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 5-hydroxymethyl-5-methyl-5,6-dihydro-4H-1,3-oxazine
• 英文别名: (5-Methyl-4,6-dihydro-1,3-oxazin-5-yl)methanol
• CAS: 202871-75-8
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: ROSBNLMJDROVIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxymethyl-5-methyl-5,6-dihydro-4H-1,3-oxazine 在 aluminum oxide 、 水 作用下， 以 乙酸乙酯 为溶剂， 生成 N-(3-Hydroxy-2-hydroxymethyl-2-methyl-propyl)-formamide
  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：

  3-甲基-3-胺甲基-1-氧杂环丁烷 在 三甲基铝 、 N,N'-二环己基碳二亚胺 作用下， 以 正己烷 、 氯苯 为溶剂， 反应 24.0h， 生成 5-hydroxymethyl-5-methyl-5,6-dihydro-4H-1,3-oxazine
  参考文献：
  名称：

  Chemoselective isomerization of amide-substituted oxetanes with Lewis acid to give oxazine derivatives or bicyclic amide acetals

  摘要：

  在路易斯酸催化下，仲酰胺和叔酰胺取代的氧杂环丁烷发生化学选择性异构化，分别生成 5-羟甲基-5,6-二氢-4H-1,3-噁嗪和由双环[2.2.2]辛烷骨架组成的活性酰胺缩醛。

  DOI：

  10.1039/a705679f

文献信息

• 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.
• Chemoselective isomerization of amide-substituted oxetanes with Lewis acid to give oxazine derivatives or bicyclic amide acetals
  作者：Tomonari Nishimura、Shigeyoshi Kanoh、Hitoshi Senda、Kohji Ando、Hiroshi Ogawa、Masatoshi Motoi、Tomonari Nishimura、Hitoshi Senda、Toshiyuki Tanaka

  DOI：10.1039/a705679f

  日期：——

  The Lewis-acid catalyzed isomerization of secondary and tertiary amide-substituted oxetanes takes place chemoselectively, giving 5-hydroxymethyl-5,6-dihydro-4H-1,3-oxazines and reactive amide acetals consisting of a bicyclo[2.2.2]octane skeleton, respectively.

  在路易斯酸催化下，仲酰胺和叔酰胺取代的氧杂环丁烷发生化学选择性异构化，分别生成 5-羟甲基-5,6-二氢-4H-1,3-噁嗪和由双环[2.2.2]辛烷骨架组成的活性酰胺缩醛。