2,3-dimethyl-3-methoxy-1,4-benzodioxen-2-ol | 110851-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2,3-dimethyl-3-methoxy-1,4-benzodioxen-2-ol
• 英文别名: 2,3-dimethyl-3-methoxy-1,4-benzodioxan-2-ol；3-methoxy-2,3-dimethyl-1,4-benzodioxin-2-ol
• CAS: 110851-14-4；110851-15-5；135831-53-7；135831-54-8
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: PLLXROIIKBLXHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,4-苯并二氧杂环己烷 在 氯化亚砜 、 sodium 、 对甲苯磺酸 、 臭氧 作用下， 以 吡啶 、 甲醇 、 乙醇 、 苯 为溶剂， 反应 11.0h， 生成 2,3-dimethyl-3-methoxy-1,4-benzodioxen-2-ol
  参考文献：
  名称：

  Photolysis of the ozonide derived from 1,4-benzodioxins. Synthesis of labile o-benzoquinones

  摘要：

  DOI：

  10.1021/jo00234a020

文献信息

• Chemical model studies on the mutagenesis of benzofuran dioxetanes in the Ames test: evidence for the benzofuran epoxide as ultimate mutagen
  作者：W. Adam、L. Hadjiarapoglou、T. Mosandl、C. R. Saha-Moeller、D. Wild

  DOI：10.1021/ja00021a029

  日期：1991.10

  The synthesis of the first benzofuran epoxide 3a was achieved by epoxidation of the benzofuran 1a with dimethyldioxirane and alternatively by deoxygenation of the benzofuran dioxetane 2a with sulfides. This labile epoxide formed with nucleophiles such as water, methanol, thiophenol, and imidazole the corresponding adducts 13a-16a. In contrast to epoxide 3a, the dioxetanes 2 required acid catalysis (CF3CO2H) for the addition of water, methanol, and azide ion to give the corresponding adducts 9-11; in the absence of nucleophiles the allylic hydroperoxides 8 were formed. The decomposition of benzofuran dioxetanes 2 in the polar, protic solvents water and methanol afforded not only expected cleavage products 4 but also the 1,3-dioxols 5, the spiroepoxide dimer 6a, and the 1,4-dioxines 7. An intramolecular electron-transfer mechanism is postulated for the formation of the spiroepoxide, which subsequently dimerizes to 6a or rearranges into 5 and 7. Only the benzofuran epoxide 3a, besides the benzofuran dioxetanes 2, was mutagenic in the Salmonella typhimurium strain TA100. Therefore, we implicate the epoxide 3a as the ultimate mutagen responsible for the high mutagenic activity observed with dioxetane 2a in the Ames test. We postulate that in the oxidative metabolism of polycyclic arenes and heteroarenes the corresponding epoxides are generated from the intermediary dioxetanes by deoxygenation with sulfides.
• KASHIMA, CHOJI;TOMOTAKE, ATSUSHI;OMOTE, YOSHIMORI, J. ORG. CHEM., 52,(1987) N 25, 5616-5621
  作者：KASHIMA, CHOJI、TOMOTAKE, ATSUSHI、OMOTE, YOSHIMORI

  DOI：——

  日期：——
• Photolysis of the ozonide derived from 1,4-benzodioxins. Synthesis of labile o-benzoquinones
  作者：Choji Kashima、Atsushi Tomotake、Yoshimori Omote

  DOI：10.1021/jo00234a020

  日期：1987.12