3,3-diethoxycarbonyl-5,6,7,8-tetrahydro-1,4-diethyl-3H-2-benzopyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3,3-diethoxycarbonyl-5,6,7,8-tetrahydro-1,4-diethyl-3H-2-benzopyran
• 英文别名: Diethyl 1,4-diethyl-5,6,7,8-tetrahydroisochromene-3,3-dicarboxylate；diethyl 1,4-diethyl-5,6,7,8-tetrahydroisochromene-3,3-dicarboxylate
• 化学式: C₁₉H₂₈O₅
• 分子量: 336.428
• InChiKey: NAPUKHAETDMCEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  酮基丙二酸二乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 bismuth(III) chloride 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到3,3-diethoxycarbonyl-5,6,7,8-tetrahydro-1,4-diethyl-3H-2-benzopyran
  参考文献：
  名称：

  Reactions of Zirconacyclopentadienes with CO, CN, and NN Moieties with Electron-Withdrawing Groups:  Formation of Six-Membered Heterocycles

  摘要：

  Reactions of zirconacyclopentadienes with diethyl ketomalonate gave alpha-pyrans in excellent yields in the presence of BiCl3. In the absence of BiCl3, zirconacyclopentadienes did not react with diethyl ketomalonate. Tetraphenylzirconacyclopentadiene reacted with diethyl ketomalonate in the presence of BiCl3 to give a ring-opening product, dienolic ether, in 53% yield. The structures of the alpha-pyran prepared from diethyldiphenylzirconacyclopentadiene and the ring-opening product were determined by X-ray analysis. When oximinosulfonate was added to tetraethylzirconacyclopentadiene in THF at -78 degrees C, 3,4,5,6-tetraethylpyridine-2-carbonitrile was obtained in 95% yield within 10 min. The structure of the product was confirmed by X-ray analysis. When tetraethylzirconacyclopentadiene was treated with azodicarboxylate in the presence of 2 equiv of CuCl at -78 degrees C, 1,2-dialkoxycarbonyl-3,4,5,6-tetraethyl-1,2-dihydropyridazine derivatives were obtained. The structure of one of dihydropyridazine was also confirmed by X-ray analysis.

  DOI：

  10.1021/ja010678u

文献信息

• Reactions of Zirconacyclopentadienes with CO, CN, and NN Moieties with Electron-Withdrawing Groups:  Formation of Six-Membered Heterocycles
  作者：Tamotsu Takahashi、Yanzhong Li、Taichi Ito、Feng Xu、Kiyohiko Nakajima、Yuanhong Liu

  DOI：10.1021/ja010678u

  日期：2002.2.1

  Reactions of zirconacyclopentadienes with diethyl ketomalonate gave alpha-pyrans in excellent yields in the presence of BiCl3. In the absence of BiCl3, zirconacyclopentadienes did not react with diethyl ketomalonate. Tetraphenylzirconacyclopentadiene reacted with diethyl ketomalonate in the presence of BiCl3 to give a ring-opening product, dienolic ether, in 53% yield. The structures of the alpha-pyran prepared from diethyldiphenylzirconacyclopentadiene and the ring-opening product were determined by X-ray analysis. When oximinosulfonate was added to tetraethylzirconacyclopentadiene in THF at -78 degrees C, 3,4,5,6-tetraethylpyridine-2-carbonitrile was obtained in 95% yield within 10 min. The structure of the product was confirmed by X-ray analysis. When tetraethylzirconacyclopentadiene was treated with azodicarboxylate in the presence of 2 equiv of CuCl at -78 degrees C, 1,2-dialkoxycarbonyl-3,4,5,6-tetraethyl-1,2-dihydropyridazine derivatives were obtained. The structure of one of dihydropyridazine was also confirmed by X-ray analysis.