3-[(1E)-3-oxobut-1-enyl]-2-methoxyphenol | 1373444-58-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[(1E)-3-oxobut-1-enyl]-2-methoxyphenol
• 英文别名: (E)-4-(3-hydroxy-2-methoxyphenyl)but-3-en-2-one
• CAS: 1373444-58-6
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: FCRZOOAUEPVFJP-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(1E)-3-oxobut-1-enyl]-2-methoxyphenol 在 碘苯二乙酸 作用下， 以 甲苯 为溶剂， 反应 49.0h， 生成 1-[(1E)-3-oxobut-1-enyl]-11,11-dimethoxy-4,4a,9,9a-tetrahydro-1H-1,4-ethanofluoren-10-one
  参考文献：
  名称：

  Diels–Alder Cycloadditions of Masked o-Benzoquinones with Alkenes

  摘要：

  Diels-Alder cycloadditions of 3-oxobut-1-enyl substituted orthoquinone monoketals with olefinic dienophiles furnished functionalized ortho-(e)ndo bicyclo[2.2.2]octenone derivatives with high regio- and stereoselectivities. The competition between self-dimerization and Diels-Alder cyclo-addition with an external dienophile usually exists, except in the case of 5-substituted orthoquinone monoketal.

  DOI：

  10.1021/acs.joc.5b01755
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 3-[(1E)-3-oxobut-1-enyl]-2-methoxyphenol
  参考文献：
  名称：

  Syntheses and X-Ray Crystal Structures of Cassiferaldehyde and Analogs

  摘要：

  Cassiferaldehyde, a recently discovered naturally occurring tyrosinase inhibitor, and six of its analogs, in which the aldehyde group has been replaced by various other functionalities, have been synthesized by a short and simple sequence starting from 2,3-dihydroxybenzaldehyde. Single-crystal x-ray structures of cassiferaldehyde as well as its methyl ketone, nitrile, and carboxylic acid analogs are reported.

  DOI：

  10.1080/00397911.2010.523921

文献信息

• Syntheses and X-Ray Crystal Structures of Cassiferaldehyde and Analogs
  作者：Jessica L. Levasseur、Dasan M. Thamattoor

  DOI：10.1080/00397911.2010.523921

  日期：2012.1.15

  Cassiferaldehyde, a recently discovered naturally occurring tyrosinase inhibitor, and six of its analogs, in which the aldehyde group has been replaced by various other functionalities, have been synthesized by a short and simple sequence starting from 2,3-dihydroxybenzaldehyde. Single-crystal x-ray structures of cassiferaldehyde as well as its methyl ketone, nitrile, and carboxylic acid analogs are reported.
• Diels–Alder Cycloadditions of Masked <i>o</i>-Benzoquinones with Alkenes
  作者：Effie Georgopanou、Katerina-Irene Martini、Panagiotis Pantazis、Paulos Pelagias、Penelope Voulgari、Lazaros P. Hadjiarapoglou

  DOI：10.1021/acs.joc.5b01755

  日期：2015.10.2

  Diels-Alder cycloadditions of 3-oxobut-1-enyl substituted orthoquinone monoketals with olefinic dienophiles furnished functionalized ortho-(e)ndo bicyclo[2.2.2]octenone derivatives with high regio- and stereoselectivities. The competition between self-dimerization and Diels-Alder cyclo-addition with an external dienophile usually exists, except in the case of 5-substituted orthoquinone monoketal.