6,7-dimethoxybenzo[d]isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 6,7-dimethoxybenzo[d]isoxazole
• 英文别名: 6,7-Dimethoxy-1,2-benzoxazole
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: RHRHQSKNTPQDRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 叠氮基三甲基硅烷 、 氯化锆(IV) 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以68%的产率得到2,3,4-三甲氧基苯甲腈
  参考文献：
  名称：

  Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

  摘要：

  The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

  DOI：

  10.1021/acs.joc.5b01305

文献信息

• US7264951B1
  申请人：——

  公开号：US7264951B1

  公开（公告）日：2007-09-04
• Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles
  作者：Phongprapan Nimnual、Jumreang Tummatorn、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1021/acs.joc.5b01305

  日期：2015.9.4

  The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.