4-cinnamyl-5-methyl-1,2-dihydroxybenzene | 62745-66-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-cinnamyl-5-methyl-1,2-dihydroxybenzene
• 英文别名: Obtusaquinone deriv jurd 2371；4-methyl-5-[(E)-3-phenylprop-2-enyl]benzene-1,2-diol
• CAS: 62745-66-8
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: ZOODPVYZFMAYIZ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-cinnamyl-5-methyl-1,2-dihydroxybenzene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 0.08h， 生成 2-hydroxy-5-methyl-4-(3-phenyl-2-propenylidene)cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Carbon-13 NMR of quinone methides

  摘要：

  AbstractThe 13C NMR spectra of four ortho‐ and seven para‐quinone methides were assigned using chemical shift and long‐range carbon‐proton coupling information. The carbonyl shifts are compared with those in ortho‐ and para‐benzoquinones. The chemical shifts of the carbonyls of the p‐quinone methides are observed at δ 186.2–186.4 for the three ortho‐di‐tert‐butyl‐substituted compounds and at δ 180.7–181.5 for the four ortho‐oxy‐substituted compounds. In the three o‐quinone methides with meta, para‐dioxy substituents, the carbonyl signals are at δ 184.2–185.4. The carbonyl signal of the one o‐quinone methide with no oxygen substitution is shifted downfield to δ 200.9, apparently as a result of hydrogen bonding to the nearby hydroxyl.

  DOI：

  10.1002/mrc.1270220206
• 作为产物：
  描述：

  3,4-二羟基甲苯 、 3-苯基丙-2-烯-1-醇 在 柠檬酸 、 维生素 C 作用下， 反应 20.0h， 生成 4-cinnamyl-5-methyl-1,2-dihydroxybenzene
  参考文献：
  名称：

  Carbon-13 NMR of quinone methides

  摘要：

  AbstractThe 13C NMR spectra of four ortho‐ and seven para‐quinone methides were assigned using chemical shift and long‐range carbon‐proton coupling information. The carbonyl shifts are compared with those in ortho‐ and para‐benzoquinones. The chemical shifts of the carbonyls of the p‐quinone methides are observed at δ 186.2–186.4 for the three ortho‐di‐tert‐butyl‐substituted compounds and at δ 180.7–181.5 for the four ortho‐oxy‐substituted compounds. In the three o‐quinone methides with meta, para‐dioxy substituents, the carbonyl signals are at δ 184.2–185.4. The carbonyl signal of the one o‐quinone methide with no oxygen substitution is shifted downfield to δ 200.9, apparently as a result of hydrogen bonding to the nearby hydroxyl.

  DOI：

  10.1002/mrc.1270220206

文献信息

• US4012529A
  申请人：——

  公开号：US4012529A

  公开（公告）日：1977-03-15