2,3-benzo-11,12-dioxa-5-azatricyclo[7.2.1.01,5]dodec-2-en-4-one | 497870-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,3-benzo-11,12-dioxa-5-azatricyclo[7.2.1.01,5]dodec-2-en-4-one
• 英文别名: 2,3-benzo-11,12-dioxa-5-azatricyclo[7.2.1.0^1,5]dodec-2-en-4-one
• CAS: 497870-46-9
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: LSZFWBHJNMJGSA-UHFFFAOYSA-N

物化性质

• 沸点：
  435.6±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3-benzo-11,12-dioxa-5-azatricyclo[7.2.1.01,5]dodec-2-en-4-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4,5-二羟基戊基)异吲哚-1,3-二酮
  参考文献：
  名称：

  Isomerization of cyclic ethers having a carbonyl functional group: new entries into different heterocyclic compounds

  摘要：

  Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00701-9
• 作为产物：
  描述：

  2-(3-(oxiran-2-yl)propyl)isoindoline-1,3-dione 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以90%的产率得到2,3-benzo-11,12-dioxa-5-azatricyclo[7.2.1.01,5]dodec-2-en-4-one
  参考文献：
  名称：

  Isomerization of cyclic ethers having a carbonyl functional group: new entries into different heterocyclic compounds

  摘要：

  Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00701-9