2-acetyl-4-methoxy-2-methyl-1,3-benzodioxole | 135831-51-5

• 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: 2-acetyl-4-methoxy-2-methyl-1,3-benzodioxole
• 英文别名: 1,3-Benzodioxole, 2-acetyl-4-methoxy-2-methyl-；1-(4-methoxy-2-methyl-1,3-benzodioxol-2-yl)ethanone
• CAS: 135831-51-5
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: AUYFZBXCMBURFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2a,7b-Dihydro-7-methoxy-2a,7b-dimethyl-1,2-dioxeto<3,4-b>benzofuran 以 甲醇 为溶剂， 反应 120.0h， 以47%的产率得到2-acetyl-3-methoxyphenyl acetate
  参考文献：
  名称：

  Chemical model studies on the mutagenesis of benzofuran dioxetanes in the Ames test: evidence for the benzofuran epoxide as ultimate mutagen

  摘要：

  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.

  DOI：

  10.1021/ja00021a029

文献信息

• BENZODIOXOLE DERIVATIVES AS WATERY ODORANTS
  申请人：Huboux Alexandre

  公开号：US20130288947A1

  公开（公告）日：2013-10-31

  The present invention relates to compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein R 1 represents a substituent of the benzene ring and is a bromine atom or a linear, branched or cyclic C 1-8 alkyl, alkenyl, alkoxy or alkenyloxy group; R 2 represents a C 1-3 alkyl group; and R 3 represents a hydrogen atom or a methyl or ethyl group; and their use as perfuming ingredients, for instance to impart odor notes of the watery/ozone type.

  本发明涉及公式（I）的化合物，其可以是其立体异构体之一或其混合物，其中R1代表苯环的取代基，可以是溴原子或线性、支链或环状C1-8烷基、烯基、烷氧基或烯氧基基团；R2代表C1-3烷基基团；R3代表氢原子或甲基或乙基基团；以及它们作为香料成分的用途，例如赋予水/臭氧型气味。
• US8987188B2
  申请人：——

  公开号：US8987188B2

  公开（公告）日：2015-03-24
• US9382500B2
  申请人：——

  公开号：US9382500B2

  公开（公告）日：2016-07-05
• [EN] BENZODIOXOLE DERIVATIVES AS WATERY ODORANTS<br/>[FR] DÉRIVÉS BENZODIOXOLES EN TANT QU'AGENTS ODORISANTS AQUEUX
  申请人：FIRMENICH & CIE

  公开号：WO2012045646A1

  公开（公告）日：2012-04-12

  The present invention relates to compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein R1 represents a substituent of the benzene ring and is a bromine atom or a linear, branched or cyclic C1-8 alkyl, alkenyl, alkoxy or alkenyloxy group; R2 represents a C1-3 alkyl group; and R3 represents a hydrogen atom or a methyl or ethyl group; and their use as perfuming ingredients, for instance to impart odor notes of the watery/ozone type.