dimethyl 7,7a-dihydro-7-oxobenzo[b]cyclopropa[e]pyran-1,1-dicarboxylate | 267402-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: dimethyl 7,7a-dihydro-7-oxobenzo[b]cyclopropa[e]pyran-1,1-dicarboxylate
• 英文别名: 2,3-dimethoxycarbonylmethanochromanone；Dimethyl 7-oxo-1a,7a-dihydrocyclopropa[b]chromene-1,1-dicarboxylate
• CAS: 267402-21-1
• 化学式: C₁₄H₁₂O₆
• 分子量: 276.246
• InChiKey: NHVQJLZIZYGWGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 7,7a-dihydro-7-oxobenzo[b]cyclopropa[e]pyran-1,1-dicarboxylate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到dimethyl (2-chloro-2,3-dihydro-4H-1-benzopyran-3-yl)malonate
  参考文献：
  名称：

  Synthesis of Tetrahydrofuro[2,3-b][1]benzopyranones by the Ring-Expansion Reaction of Methanochromanone with Symmetric Ketones

  摘要：

  In the presence of SnCl4, 2,3-dimethoxycarbonylmethanochromanone (8) was transformed into a zwitterion which easily reacted with symmetric ketones to give the tetrahydrofuro[2,3-b][1]benzopyranone derivatives in good yields with high diastereoselectivity.

  DOI：

  10.3987/com-99-8810
• 作为产物：
  描述：

  3-碘代色酮,97 、 丙二酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到dimethyl 7,7a-dihydro-7-oxobenzo[b]cyclopropa[e]pyran-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of Tetrahydrofuro[2,3-b][1]benzopyranones by the Ring-Expansion Reaction of Methanochromanone with Symmetric Ketones

  摘要：

  In the presence of SnCl4, 2,3-dimethoxycarbonylmethanochromanone (8) was transformed into a zwitterion which easily reacted with symmetric ketones to give the tetrahydrofuro[2,3-b][1]benzopyranone derivatives in good yields with high diastereoselectivity.

  DOI：

  10.3987/com-99-8810

文献信息

• Diastereoselective Ring-Expansion Reaction of Methanochromanone with Aldehydes: Formation of trans-Fused Tetrahydrofuro[2,3-b][1]benzopyranones and Their Isomerization
  作者：Yoshiaki Sugita、Kazuyoshi Kawai、Ichiro Yokoe

  DOI：10.3987/com-00-9071

  日期：——

  In the presence of SnCl4, 2,3-dimethoxycarbonylmethanochromanone (4) was transformed into a zwitter-ion which easily reacted with aldehydes to give the trans-fused tetrahydrofuro[2,3-b] [1]benzopyranones in good yields with high diastereoselectivity. cis-l;used furobenzopyranone derivatives were also obtained in good yields by isomerization of the trans isomers.
• Synthesis of Tetrahydrofuro[2,3-b][1]benzopyranones by the Ring-Expansion Reaction of Methanochromanone with Symmetric Ketones
  作者：Yoshiaki Sugita、Kazuyoshi Kawai、Ichiro Yokoe

  DOI：10.3987/com-99-8810

  日期：——

  In the presence of SnCl4, 2,3-dimethoxycarbonylmethanochromanone (8) was transformed into a zwitterion which easily reacted with symmetric ketones to give the tetrahydrofuro[2,3-b][1]benzopyranone derivatives in good yields with high diastereoselectivity.