7-Diethoxymethylene-2,3-dioxa-bicyclo[2.2.1]hept-5-ene | 167901-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 7-Diethoxymethylene-2,3-dioxa-bicyclo[2.2.1]hept-5-ene
• 英文别名: 7-(Diethoxymethylidene)-2,3-dioxabicyclo[2.2.1]hept-5-ene
• CAS: 167901-23-7
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: SFCNSYOTTJMCOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Diethoxymethylene-2,3-dioxa-bicyclo[2.2.1]hept-5-ene 在 水 作用下， 以 丙酮 为溶剂， 生成 (1S,4R,7S)-2,3-Dioxa-bicyclo[2.2.1]hept-5-ene-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  Sensitized Photooxygenation of 6-Heteroatom-Substituted Fulvenes: Primary Products and Their Chemical Transformations

  摘要：

  Sensitized photooxygenation of 6,6-diethoxyfulvene (1) and 6,6-(ethylenedithio)fulvene (9) at -78 degrees C afforded diethoxyfulvene endoperoxide 2 and (ethylenedithio)fulvene endoperoxide 10, respectively, as primary products. Further irradiation resulted in formation of the novel bisperoxides 3 and 11 from [2 + 2] cycloaddition of O-1(2) to the exocyclic double bond of the corresponding endoperoxides. The initial endoperoxides were characterized by NMR at low temperature and underwent a variety of chemical transformations to give highly oxygenated cyclopentane derivatives. In contrast, photooxygenation of 6,6-dipiperidinofulvene (16) and 6-(dimethylamino)fulvene (17) did not lead to chemical reaction; these compounds physically quench O-1(2) with rate constants on the order of 10(8) M(-1) s(-1).

  DOI：

  10.1021/jo00110a043
• 作为产物：
  描述：

  6,6-diethoxyfulvene 在 氧气 、 rose bengal 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 7-Diethoxymethylene-2,3-dioxa-bicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  Sensitized Photooxygenation of 6-Heteroatom-Substituted Fulvenes: Primary Products and Their Chemical Transformations

  摘要：

  Sensitized photooxygenation of 6,6-diethoxyfulvene (1) and 6,6-(ethylenedithio)fulvene (9) at -78 degrees C afforded diethoxyfulvene endoperoxide 2 and (ethylenedithio)fulvene endoperoxide 10, respectively, as primary products. Further irradiation resulted in formation of the novel bisperoxides 3 and 11 from [2 + 2] cycloaddition of O-1(2) to the exocyclic double bond of the corresponding endoperoxides. The initial endoperoxides were characterized by NMR at low temperature and underwent a variety of chemical transformations to give highly oxygenated cyclopentane derivatives. In contrast, photooxygenation of 6,6-dipiperidinofulvene (16) and 6-(dimethylamino)fulvene (17) did not lead to chemical reaction; these compounds physically quench O-1(2) with rate constants on the order of 10(8) M(-1) s(-1).

  DOI：

  10.1021/jo00110a043

文献信息

• Sensitized Photooxygenation of 6-Heteroatom-Substituted Fulvenes: Primary Products and Their Chemical Transformations
  作者：Xiaojun Zhang、Feng Lin、Christopher S. Foote

  DOI：10.1021/jo00110a043

  日期：1995.3

  Sensitized photooxygenation of 6,6-diethoxyfulvene (1) and 6,6-(ethylenedithio)fulvene (9) at -78 degrees C afforded diethoxyfulvene endoperoxide 2 and (ethylenedithio)fulvene endoperoxide 10, respectively, as primary products. Further irradiation resulted in formation of the novel bisperoxides 3 and 11 from [2 + 2] cycloaddition of O-1(2) to the exocyclic double bond of the corresponding endoperoxides. The initial endoperoxides were characterized by NMR at low temperature and underwent a variety of chemical transformations to give highly oxygenated cyclopentane derivatives. In contrast, photooxygenation of 6,6-dipiperidinofulvene (16) and 6-(dimethylamino)fulvene (17) did not lead to chemical reaction; these compounds physically quench O-1(2) with rate constants on the order of 10(8) M(-1) s(-1).