3-(4-bromobenzyl)-8-methoxybenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxide | 1350309-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-bromobenzyl)-8-methoxybenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxide
• 英文别名: 3-[(4-Bromophenyl)methyl]-8-methoxy-2,2-dioxo-1,2lambda6-benzoxathiin-4-one；3-[(4-bromophenyl)methyl]-8-methoxy-2,2-dioxo-1,2λ6-benzoxathiin-4-one
• CAS: 1350309-16-8
• 化学式: C₁₆H₁₃BrO₅S
• 分子量: 397.246
• InChiKey: VPFHNHBJCUNBFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-2-(4-bromophenyl)ethenesulfonyl chloride 、 邻香草醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 以85%的产率得到3-(4-bromobenzyl)-8-methoxybenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxide
  参考文献：
  名称：

  Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences

  摘要：

  We have developed a solvent-dependent method for the synthesis of novel benzo-delta-sultone scaffolds. A variety of benzylbenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxides were obtained in high yields in DMF using a one-pot, DBU-catalyzed condensation of 2-hydroxybenzaldehydes with a number of (E)-2-phenylethenesulfonyl chlorides. On the other hand, the initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonate derivatives underwent DBU-catalyzed reactions to a series of 3-[methoxy(phenyl)methyl]benzo[e][1,2]oxathiine-2,2-dioxides in moderate to good yields in MeOH. These reactions presumably proceed via DBU-catalyzed O-sulfonylation/intramolecular Baylis-Hillman/1,3-H shift or dehydration tandem sequences, respectively.

  DOI：

  10.1021/jo201506d

文献信息

• Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences
  作者：Mehdi Ghandi、Abolfazl Hasani Bozcheloei、Seyed Hadi Nazari、Masoud Sadeghzadeh

  DOI：10.1021/jo201506d

  日期：2011.12.16

  We have developed a solvent-dependent method for the synthesis of novel benzo-delta-sultone scaffolds. A variety of benzylbenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxides were obtained in high yields in DMF using a one-pot, DBU-catalyzed condensation of 2-hydroxybenzaldehydes with a number of (E)-2-phenylethenesulfonyl chlorides. On the other hand, the initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonate derivatives underwent DBU-catalyzed reactions to a series of 3-[methoxy(phenyl)methyl]benzo[e][1,2]oxathiine-2,2-dioxides in moderate to good yields in MeOH. These reactions presumably proceed via DBU-catalyzed O-sulfonylation/intramolecular Baylis-Hillman/1,3-H shift or dehydration tandem sequences, respectively.