5,6-dihydro-2-hydroxy-6-methyl-2,3-diphenyl-2H-1,4-oxazine | 141089-09-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5,6-dihydro-2-hydroxy-6-methyl-2,3-diphenyl-2H-1,4-oxazine
• 英文别名: 5,6-dihydro-6-methyl-2,3-diphenyl-2H-1,4-oxazine-2-ol；2-methyl-5,6-diphenyl-2,3-dihydro-1,4-oxazin-6-ol
• CAS: 141089-09-0
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: RGUOETRUCFLKIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-2-hydroxy-6-methyl-2,3-diphenyl-2H-1,4-oxazine 、 苯氧乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以73%的产率得到4-benzoyl-1-(2-hydroxypropyl)-3-phenoxy-4-phenylazetidinone
  参考文献：
  名称：

  Sharma; Venugopalan, Paloth; Bhaduri, Susmita, Journal of Chemical Research - Part S, 2003, # 3, p. 170 - 171

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基乙酮 、 异丙醇胺 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以86%的产率得到5,6-dihydro-2-hydroxy-6-methyl-2,3-diphenyl-2H-1,4-oxazine
  参考文献：
  名称：

  Sheikhshoaie, Iran; Belaj, Ferdinand; Kamali, Ahmad, Bulletin of the Chemical Society of Ethiopia, 2010, vol. 24, # 2, p. 283 - 287

  摘要：

  DOI：

文献信息

• Reaction of .alpha.-diketones with 2-amino alcohols. Intramolecular competitive 6-exo-trig vs 5-endo-trig processes. A systematic and kinetic study
  作者：Benito Alcaide、Joaquin Plumet、Ignacio M. Rodriguez-Campos、Severino Garcia-Blanco、Sagrario Martinez-Carrera

  DOI：10.1021/jo00034a046

  日期：1992.4

  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.