6-bromo-5-hydroxy-7,8-dihydrodinaphth[1,2-b:2',3'-f ]oxepine-9,14-dione | 1374687-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-5-hydroxy-7,8-dihydrodinaphth[1,2-b:2',3'-f ]oxepine-9,14-dione
• 英文别名: 11-Bromo-10-hydroxy-2-oxapentacyclo[13.8.0.03,12.04,9.017,22]tricosa-1(15),3(12),4,6,8,10,17,19,21-nonaene-16,23-dione
• CAS: 1374687-90-7
• 化学式: C₂₂H₁₃BrO₄
• 分子量: 421.247
• InChiKey: OFRLNZGGVMDGFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-3-甲基萘-1,4-二酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 六甲基二锡 、 sodium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以96%的产率得到6-bromo-5-hydroxy-7,8-dihydrodinaphth[1,2-b:2',3'-f ]oxepine-9,14-dione
  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.