2-Butanone, 3-[(2-hydroxyethyl)imino]- (9CI) | 130028-26-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Butanone, 3-[(2-hydroxyethyl)imino]- (9CI)
• 英文别名: 3-[(Z)-2-Hydroxy-ethylimino]-butan-2-one
• CAS: 130028-26-1
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: WNLUWYXJABQCQE-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.66
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Butanone, 3-[(2-hydroxyethyl)imino]- (9CI) 以 氘代氯仿 为溶剂， 生成 乙酮,1-(2-甲基-2-[口噁]唑烷基)-(9CI)
  参考文献：
  名称：

  Reaction of .alpha.-diketones with 2-amino alcohols. Intramolecular competitive 6-exo-trig vs 5-endo-trig processes. A systematic and kinetic study

  摘要：

  2-Aminoethanol and C-substituted derivatives 1 react with diacetyl, benzil, and 1-phenyl-1,2-propanedione, models of alpha-diketones 2 to give with remarkable regio- and stereoselectivity 2-hydroxy-5,6-dihydro-2H-1,4-oxazines 3, cis-octahydro[1,4]oxazino[3,2-b]oxazines 4, alpha-imino ketones 6, 2-acetyl-1,3-oxazolidines 7, N,N'-bis(2-hydroxy-2-methylpropyl)-2,3-butanediimines 8, and 2,2'-dimethyl-2,2'-bioxazolidines 9 depending on the nature of the reagents and the reaction conditions. On the basis of isolated intermediates, a reasonable mechanism taking into account the stereoelectronic effects observed on the cyclization has been proposed for these processes. In addition, a kinetic study of the ring-chain-ring tautomeric equilibrium of oxazines 3a-c, 3i-k, and 3o-q has been studied by H-1 NMR and C-13 NMR. In solution, compounds 3a-c and 3i-k exhibit a three-component tautomeric equilibria consisting of the following: the beta-iminohemiacetal 3, the beta-hydroxyimino ketone 6, and the 2-acetyl- or 2-benzoyl-1,3-oxazolidine 7. The calculated rate constants for this process show that the equilibrium is shifted toward the formation of the five-membered ring by 0.4-4.8 kJ mol-1 over the six-membered ring depending on the substitution patterns. Compounds 3p-q exist in solution as equimolar mixtures of the ring and open-chain tautomers. Compound 3o exists predominantly in the open-chain form. In addition, 2-acylthiazolidines 13a-c do not evidence any dynamic processes in solution.

  DOI：

  10.1021/jo00034a046
• 作为产物：
  描述：

  乙酮,1-(2-甲基-2-[口噁]唑烷基)-(9CI) 以 氘代氯仿 为溶剂， 生成 2-Butanone, 3-[(2-hydroxyethyl)imino]- (9CI)
  参考文献：
  名称：

  Reaction of .alpha.-diketones with 2-amino alcohols. Intramolecular competitive 6-exo-trig vs 5-endo-trig processes. A systematic and kinetic study

  摘要：

  2-Aminoethanol and C-substituted derivatives 1 react with diacetyl, benzil, and 1-phenyl-1,2-propanedione, models of alpha-diketones 2 to give with remarkable regio- and stereoselectivity 2-hydroxy-5,6-dihydro-2H-1,4-oxazines 3, cis-octahydro[1,4]oxazino[3,2-b]oxazines 4, alpha-imino ketones 6, 2-acetyl-1,3-oxazolidines 7, N,N'-bis(2-hydroxy-2-methylpropyl)-2,3-butanediimines 8, and 2,2'-dimethyl-2,2'-bioxazolidines 9 depending on the nature of the reagents and the reaction conditions. On the basis of isolated intermediates, a reasonable mechanism taking into account the stereoelectronic effects observed on the cyclization has been proposed for these processes. In addition, a kinetic study of the ring-chain-ring tautomeric equilibrium of oxazines 3a-c, 3i-k, and 3o-q has been studied by H-1 NMR and C-13 NMR. In solution, compounds 3a-c and 3i-k exhibit a three-component tautomeric equilibria consisting of the following: the beta-iminohemiacetal 3, the beta-hydroxyimino ketone 6, and the 2-acetyl- or 2-benzoyl-1,3-oxazolidine 7. The calculated rate constants for this process show that the equilibrium is shifted toward the formation of the five-membered ring by 0.4-4.8 kJ mol-1 over the six-membered ring depending on the substitution patterns. Compounds 3p-q exist in solution as equimolar mixtures of the ring and open-chain tautomers. Compound 3o exists predominantly in the open-chain form. In addition, 2-acylthiazolidines 13a-c do not evidence any dynamic processes in solution.

  DOI：

  10.1021/jo00034a046

文献信息

• Anatomy of a three species tautomeric process: The ring-chain tautomerism in 5,6-dihydro-2-hydroxy-2,3-dimethyl-2H-1,4-oxazine
  作者：Benito Alcaide、Ramon González Rubio、Joaquín Plumet、Ignacio M. Rodriguez-Campos

  DOI：10.1016/s0040-4039(00)97584-1

  日期：1990.1

  A ring-chain tautomerism involving two single processes hydroxyketone-hemiacetal and hydroxyimine-1,3-oxazolidine is kinetically studied.

  动力学研究了涉及两个单一过程的羟基酮-半缩醛和羟基亚胺-1,3-恶唑烷的环链互变异构现象。