1,2,3,4-tetrahydro-5,6-methylenedioxy-1,10-phenanthroline | 346433-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 1,2,3,4-tetrahydro-5,6-methylenedioxy-1,10-phenanthroline
• 英文别名: 8,9,10,11-Tetrahydro-[1,3]dioxolo[4,5-f][1,10]phenanthroline
• CAS: 346433-16-7
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: LJRIPVBYFXATNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  43.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-5,6-methylenedioxy-1,10-phenanthroline 在 水 作用下， 以 氯仿 为溶剂， 以89%的产率得到1,2,3,4-tetrahydro-1,10-phenanthroline-5,6-dione
  参考文献：
  名称：

  Solvent effect on the reactivity of 1,10-phenanthroline-5,6-dione towards diazomethane

  摘要：

  In an aprotic medium, such as THF, Et2O or CH2Cl2, the reaction of 1,10-phenanthroline-5,6-dione with diazomethane gave 5,6-methylenedioxy- 1,10-phenanthroline as the only product. In contrast, in a protic solvent, such as 2-propanol or ethanol, the nucleophilic attack of CH2N2 occurred on carbonyl carbons, resulting in the formation of dispiro[5,6-dihydro-1,10-phenanthroline-5,6-dioxirane] as the main product. When the reaction with CH2N2 was carried out in methanol, the only product which could be isolated from the reaction mixture, dimethyl 2,2'-bipyridine-3,3'-dicarboxylate, resulted from a break of the C(5)-C(6) bridge. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00122-3
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 20.0 ℃ 、55.0 kPa 条件下， 反应 3.0h， 生成 1,2,3,4-tetrahydro-5,6-methylenedioxy-1,10-phenanthroline
  参考文献：
  名称：

  Solvent effect on the reactivity of 1,10-phenanthroline-5,6-dione towards diazomethane

  摘要：

  In an aprotic medium, such as THF, Et2O or CH2Cl2, the reaction of 1,10-phenanthroline-5,6-dione with diazomethane gave 5,6-methylenedioxy- 1,10-phenanthroline as the only product. In contrast, in a protic solvent, such as 2-propanol or ethanol, the nucleophilic attack of CH2N2 occurred on carbonyl carbons, resulting in the formation of dispiro[5,6-dihydro-1,10-phenanthroline-5,6-dioxirane] as the main product. When the reaction with CH2N2 was carried out in methanol, the only product which could be isolated from the reaction mixture, dimethyl 2,2'-bipyridine-3,3'-dicarboxylate, resulted from a break of the C(5)-C(6) bridge. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00122-3

文献信息

• Solvent effect on the reactivity of 1,10-phenanthroline-5,6-dione towards diazomethane
  作者：Wiesław Z Antkowiak、Adam Sobczak

  DOI：10.1016/s0040-4020(01)00122-3

  日期：2001.4

  In an aprotic medium, such as THF, Et2O or CH2Cl2, the reaction of 1,10-phenanthroline-5,6-dione with diazomethane gave 5,6-methylenedioxy- 1,10-phenanthroline as the only product. In contrast, in a protic solvent, such as 2-propanol or ethanol, the nucleophilic attack of CH2N2 occurred on carbonyl carbons, resulting in the formation of dispiro[5,6-dihydro-1,10-phenanthroline-5,6-dioxirane] as the main product. When the reaction with CH2N2 was carried out in methanol, the only product which could be isolated from the reaction mixture, dimethyl 2,2'-bipyridine-3,3'-dicarboxylate, resulted from a break of the C(5)-C(6) bridge. (C) 2001 Elsevier Science Ltd. All rights reserved.