4-叠氮基-2-甲氧基苯甲酸甲酯 | 87587-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-叠氮基-2-甲氧基苯甲酸甲酯
• 英文名称: methyl 4-azido-2-methoxybenzoate
• 英文别名: Benzoic acid, 4-azido-2-methoxy-, methyl ester
• CAS: 87587-56-2
• 化学式: C₉H₉N₃O₃
• 分子量: 207.189
• InChiKey: YERBTTJZOUVQCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-叠氮基-2-甲氧基苯甲酸甲酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (4-Azido-2-methoxyphenyl)methanol
  参考文献：
  名称：

  An efficient synthesis of a class of heterobifunctional photo-reactive crosslinkers, labels, and probes

  摘要：

  Aryl esters are selectively reduced with DIBAL-H in the presence of an azide functional group to provide access to 4-azido-2-alkoxybenzaldehydes in five steps with overall yields ranging from 72 to 78%. This methodology improves traditional approaches to this class of compounds, which suffer from poor overall yields (4-11%). Out approach can be used to synthesize a variety of new aryl azide cross-linkers, labels, and probes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00131-9
• 作为产物：
  描述：

  4-氨基水杨酸 在 sodium azide 、 硫酸 、 三氟化硼乙醚 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 4-叠氮基-2-甲氧基苯甲酸甲酯
  参考文献：
  名称：

  An efficient synthesis of a class of heterobifunctional photo-reactive crosslinkers, labels, and probes

  摘要：

  Aryl esters are selectively reduced with DIBAL-H in the presence of an azide functional group to provide access to 4-azido-2-alkoxybenzaldehydes in five steps with overall yields ranging from 72 to 78%. This methodology improves traditional approaches to this class of compounds, which suffer from poor overall yields (4-11%). Out approach can be used to synthesize a variety of new aryl azide cross-linkers, labels, and probes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00131-9

文献信息

• Approaches to azepines: a new azepine by the photolysis of dimethyl p-azidosalicylate
  作者：Reginald A. Mustill、Alun H. Rees

  DOI：10.1021/jo00173a048

  日期：1983.12
• MUSTILL, R. A.;REES, A. H., J. ORG. CHEM., 1983, 48, N 25, 5041-5043
  作者：MUSTILL, R. A.、REES, A. H.

  DOI：——

  日期：——
• An efficient synthesis of a class of heterobifunctional photo-reactive crosslinkers, labels, and probes
  作者：Kyle W Gano、Harold G Monbouquette、David C Myles

  DOI：10.1016/s0040-4039(01)00131-9

  日期：2001.3

  Aryl esters are selectively reduced with DIBAL-H in the presence of an azide functional group to provide access to 4-azido-2-alkoxybenzaldehydes in five steps with overall yields ranging from 72 to 78%. This methodology improves traditional approaches to this class of compounds, which suffer from poor overall yields (4-11%). Out approach can be used to synthesize a variety of new aryl azide cross-linkers, labels, and probes. (C) 2001 Elsevier Science Ltd. All rights reserved.