methyl 5-formyl-6-hydroxy-2-phenyl-2H-benzo[b][1,4]oxazine-3-carboxylate | 1354521-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: methyl 5-formyl-6-hydroxy-2-phenyl-2H-benzo[b][1,4]oxazine-3-carboxylate
• 英文别名: methyl 5-formyl-6-hydroxy-2-phenyl-2H-1,4-benzoxazine-3-carboxylate
• CAS: 1354521-76-8
• 化学式: C₁₇H₁₃NO₅
• 分子量: 311.294
• InChiKey: ZNAIYFDMUHLDCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  527.3±60.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯甲醛 、 甲基 3-苯基-DL-丙氨酸酯 在 magnesium sulfate 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以75%的产率得到methyl 5-formyl-6-hydroxy-2-phenyl-2H-benzo[b][1,4]oxazine-3-carboxylate
  参考文献：
  名称：

  Sequential C–N and C–O Bond Formation in a Single Pot: Synthesis of 2H-Benzo[b][1,4]oxazines from 2,5-Dihydroxybenzaldehyde and Amino acid Precursors

  摘要：

  Functionalized beta-aryl alanine ester derivatives were found to undergo rapid C-N and C-O bond formation with quinol carbonyl compounds to afford 2H-benzo[b][1,4]oxazines in good to excellent yields. This unprecedented finding reported herein offers a straightforward, highly efficient, and rapid method for the synthesis of 2H-benzo[b][1,4]oxazines.

  DOI：

  10.1021/ol2031747

文献信息

• Sequential C–N and C–O Bond Formation in a Single Pot: Synthesis of 2<i>H</i>-Benzo[<i>b</i>][1,4]oxazines from 2,5-Dihydroxybenzaldehyde and Amino acid Precursors
  作者：Javed Iqbal、Neelima D. Tangellamudi、Balakrishna Dulla、Sridhar Balasubramanian

  DOI：10.1021/ol2031747

  日期：2012.1.20

  Functionalized beta-aryl alanine ester derivatives were found to undergo rapid C-N and C-O bond formation with quinol carbonyl compounds to afford 2H-benzo[b][1,4]oxazines in good to excellent yields. This unprecedented finding reported herein offers a straightforward, highly efficient, and rapid method for the synthesis of 2H-benzo[b][1,4]oxazines.