methyl 3-methoxy-4-oxospiro[cyclohexa[2,5]diene-1,5'-indeno[5,6-d][1,3]dioxole]-6'-carboxylate | 1426853-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: methyl 3-methoxy-4-oxospiro[cyclohexa[2,5]diene-1,5'-indeno[5,6-d][1,3]dioxole]-6'-carboxylate
• 英文别名: Methyl 1-methoxy-6-oxospiro[cyclohexa-1,4-diene-3,7'-cyclopenta[f][1,3]benzodioxole]-6'-carboxylate；methyl 1-methoxy-6-oxospiro[cyclohexa-1,4-diene-3,7'-cyclopenta[f][1,3]benzodioxole]-6'-carboxylate
• CAS: 1426853-57-7
• 化学式: C₁₈H₁₄O₆
• 分子量: 326.306
• InChiKey: ATPOHJJSAMJVNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-methyl 3-(benzo[d][1,3]dioxol-5-yl)-2-(4-hydroxy-3-methoxyphenyl)acrylate 在 三氟乙酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以95%的产率得到methyl 3-methoxy-4-oxospiro[cyclohexa[2,5]diene-1,5'-indeno[5,6-d][1,3]dioxole]-6'-carboxylate
  参考文献：
  名称：

  Bioinspired Construction of a Spirocyclohexadienone Moiety via Sodium Nitrite Catalyzed Aerobic Intramolecular Oxidative Phenol Coupling

  摘要：

  An efficient and green intramolecular oxidative phenol coupling for the direct construction of spirocyclohexadienones has been developed, which uses environment-friendly sodium nitrite as the catalyst and oxygen in the air as the terminal oxidant. Hydroxy-containing substituted phenanthrenes and dibenzoazepines could be easily obtained from the dienone-phenol rearrangement.

  DOI：

  10.1021/ol400388j

文献信息

• Bioinspired Construction of a Spirocyclohexadienone Moiety via Sodium Nitrite Catalyzed Aerobic Intramolecular Oxidative Phenol Coupling
  作者：Bo Su、Meng Deng、Qingmin Wang

  DOI：10.1021/ol400388j

  日期：2013.4.5

  An efficient and green intramolecular oxidative phenol coupling for the direct construction of spirocyclohexadienones has been developed, which uses environment-friendly sodium nitrite as the catalyst and oxygen in the air as the terminal oxidant. Hydroxy-containing substituted phenanthrenes and dibenzoazepines could be easily obtained from the dienone-phenol rearrangement.