2-bromo-3,6-dimethyl-1,4-naphthoquinone | 31478-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-3,6-dimethyl-1,4-naphthoquinone
• 英文别名: 2-Bromo-3,6-dimethylnaphthalene-1,4-dione
• CAS: 31478-89-4
• 化学式: C₁₂H₉BrO₂
• 分子量: 265.106
• InChiKey: KKHXFIZNYOIPFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-3,6-dimethyl-1,4-naphthoquinone 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以71%的产率得到(7aRS,13aRS,13bSR)-6-bromo-13a,13b-epoxy-2,7a,10-trimethyl-7H-dibenzo[b,g]fluorene-5,8,13-trione
  参考文献：
  名称：

  Three Different Dimerizations of 2-Bromo-3-methyl-1,4-naphthoquinones

  摘要：

  Three types of dimeric naphthoquinones, which possess structurally diverse skeletons, can be prepared in one step from 2-bromo-3-methyl-1,4-naphthoquinones. 2,2'-Dimeric naphthoquinones were prepared by a one-pot Stille-type reaction via vinylstannanes. Oxepines are formed by unexpected domino reactions via 1,4-dihydroxynaphthalene species. Epoxides are formed by a Michael/Darzens reaction via the o-quinone methides.

  DOI：

  10.1021/jo300696m
• 作为产物：
  描述：

  2,7-二甲基-1,4-萘醌 在 溴 、 溶剂黄146 作用下， 反应 12.0h， 以83%的产率得到2-bromo-3,6-dimethyl-1,4-naphthoquinone
  参考文献：
  名称：

  Three Different Dimerizations of 2-Bromo-3-methyl-1,4-naphthoquinones

  摘要：

  Three types of dimeric naphthoquinones, which possess structurally diverse skeletons, can be prepared in one step from 2-bromo-3-methyl-1,4-naphthoquinones. 2,2'-Dimeric naphthoquinones were prepared by a one-pot Stille-type reaction via vinylstannanes. Oxepines are formed by unexpected domino reactions via 1,4-dihydroxynaphthalene species. Epoxides are formed by a Michael/Darzens reaction via the o-quinone methides.

  DOI：

  10.1021/jo300696m

文献信息

• Three Different Dimerizations of 2-Bromo-3-methyl-1,4-naphthoquinones
  作者：Shuhei Azuma、Kazuyuki Nishio、Konomi Kubo、Takahiro Sasamori、Norihiro Tokitoh、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1021/jo300696m

  日期：2012.5.18

  Three types of dimeric naphthoquinones, which possess structurally diverse skeletons, can be prepared in one step from 2-bromo-3-methyl-1,4-naphthoquinones. 2,2'-Dimeric naphthoquinones were prepared by a one-pot Stille-type reaction via vinylstannanes. Oxepines are formed by unexpected domino reactions via 1,4-dihydroxynaphthalene species. Epoxides are formed by a Michael/Darzens reaction via the o-quinone methides.