6-hydroxymethyl-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine | 847834-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-hydroxymethyl-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine
• 英文别名: [3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazin-6-yl]methanol；[3-(4-methoxyphenyl)-5,6-dihydro-4H-oxazin-6-yl]methanol
• CAS: 847834-47-3
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: PZNKRAGGDGNOEG-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  357.5±48.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxymethyl-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以35%的产率得到[5-Bromomethyl-dihydro-furan-(2E)-ylidene]-(4-methoxy-phenyl)-amine
  参考文献：
  名称：

  One-Pot Cyclizations of Dilithiated Oximes and Hydrazones with Epibromohydrin. Efficient Synthesis of 6-Hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and Oxazolo[3,4-b]pyridazin-7-ones

  摘要：

  [GRAPHICS]The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with epibromohydrin afforded oxazolo[3,4-b]pyridazin-7-ones, which were formed by a novel domino cyclization.

  DOI：

  10.1021/jo052329e
• 作为产物：
  描述：

  (E)-1-(4-methoxyphenyl)ethanone oxime 、 环氧溴丙烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以73%的产率得到6-hydroxymethyl-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine
  参考文献：
  名称：

  One-Pot Cyclizations of Dilithiated Oximes and Hydrazones with Epibromohydrin. Efficient Synthesis of 6-Hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and Oxazolo[3,4-b]pyridazin-7-ones

  摘要：

  [GRAPHICS]The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with epibromohydrin afforded oxazolo[3,4-b]pyridazin-7-ones, which were formed by a novel domino cyclization.

  DOI：

  10.1021/jo052329e

文献信息

• Synthesis of new series of 5,6-dihydro-4H-1,2-oxazines via hetero Diels–Alder reaction and evaluation of antimicrobial activity
  作者：M.K. Manjula、K.M.L. Rai、S.L. Gaonkar、K.A. Raveesha、S. Satish

  DOI：10.1016/j.ejmech.2008.02.027

  日期：2009.1

  A new series of 5,6-dihydro-4H-1,2-oxazines were synthesized via hetero Diels-Alder reaction of alpha-nitrosoolefins with alkenes. alpha-Nitrosoolefins were generated from ketoximes by the action of chloramine-T. The newly synthesized compounds were characterized with IR, NMR, elemental analysis and screened for their antimicrobial activity; they exhibited excellent antimicrobial activity. The minimal inhibitory concentration of the compounds was in the range of 10-35 mu g ml(-1) for bacteria and 10-40 mu g ml(-1) for fungi. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines by one-pot-cyclization of dilithiated oximes with epibromohydrin
  作者：Uwe Albrecht、Katrin Gerwien、Peter Langer

  DOI：10.1016/j.tetlet.2004.12.031

  日期：2005.2

  6-Hydroxymethyl-5,6-dihydro-4H-1,2-oxazines were regioselectively prepared by one-pot cyclization of dilithiated oximes with epibromohydrin. (C) 2004 Elsevier Ltd. All rights reserved.
• One-Pot Cyclizations of Dilithiated Oximes and Hydrazones with Epibromohydrin. Efficient Synthesis of 6-Hydroxymethyl-5,6-dihydro-4<i>H</i>-1,2-oxazines and Oxazolo[3,4-<i>b</i>]pyridazin-7-ones
  作者：Tuan Thanh Dang、Uwe Albrecht、Katrin Gerwien、Melanie Siebert、Peter Langer

  DOI：10.1021/jo052329e

  日期：2006.3.1

  [GRAPHICS]The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with epibromohydrin afforded oxazolo[3,4-b]pyridazin-7-ones, which were formed by a novel domino cyclization.