3-(benzyloxy)-2-bromo-5-methoxytoluene | 36776-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(benzyloxy)-2-bromo-5-methoxytoluene
• 英文别名: 3-Benzyloxy-2-brom-5-methoxytoluol；Toluene, 3-benzyloxy-2-bromo-5-methoxy-；2-bromo-5-methoxy-1-methyl-3-phenylmethoxybenzene
• CAS: 36776-45-1
• 化学式: C₁₅H₁₅BrO₂
• 分子量: 307.187
• InChiKey: OJXQPHYANJEHNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苄基-5-甲基苯-1,3-二醇 、 3-(benzyloxy)-2-bromo-5-methoxytoluene 在 吡啶 、 potassium carbonate 、 copper(II) oxide 作用下， 生成 2,3'-bis(benzyloxy)-5',6-dimethyl-4-methoxydiphenyl ether
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of Cyperin

  摘要：

  Cyperin is a phytotoxic diphenyl ether natural product. Total synthesis of cyperin has been achieved and its herbicidal activity evaluated. The synthesis is highlighted by an Ullmann coupling to construct the diphenyl ether moiety contained within cyperin. It was found that cyperin inhibited root growth of Cyperus rotundus grown on agar; however, root growth of Cyperus grown in soil was unaffected. Cyperin also inhibited growth of Arabidopsis thaliana and Agrostis palustris grown in agar. The mode of action of cyperin is different from that of commercial diphenyl ether herbicides that inhibit protoporphyrinogen oxidase.

  DOI：

  10.1021/jf00051a046
• 作为产物：
  描述：

  2-bromo-3-hydroxy-5-methoxytoluene 、 溴甲苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以91%的产率得到3-(benzyloxy)-2-bromo-5-methoxytoluene
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of Cyperin

  摘要：

  Cyperin is a phytotoxic diphenyl ether natural product. Total synthesis of cyperin has been achieved and its herbicidal activity evaluated. The synthesis is highlighted by an Ullmann coupling to construct the diphenyl ether moiety contained within cyperin. It was found that cyperin inhibited root growth of Cyperus rotundus grown on agar; however, root growth of Cyperus grown in soil was unaffected. Cyperin also inhibited growth of Arabidopsis thaliana and Agrostis palustris grown in agar. The mode of action of cyperin is different from that of commercial diphenyl ether herbicides that inhibit protoporphyrinogen oxidase.

  DOI：

  10.1021/jf00051a046

文献信息

• Synthesis and Herbicidal Activity of Cyperin
  作者：Philip M. Harrington、Bijay K. Singh、Iwona T. Szamosi、Jeffrey H. Birk

  DOI：10.1021/jf00051a046

  日期：1995.3

  Cyperin is a phytotoxic diphenyl ether natural product. Total synthesis of cyperin has been achieved and its herbicidal activity evaluated. The synthesis is highlighted by an Ullmann coupling to construct the diphenyl ether moiety contained within cyperin. It was found that cyperin inhibited root growth of Cyperus rotundus grown on agar; however, root growth of Cyperus grown in soil was unaffected. Cyperin also inhibited growth of Arabidopsis thaliana and Agrostis palustris grown in agar. The mode of action of cyperin is different from that of commercial diphenyl ether herbicides that inhibit protoporphyrinogen oxidase.

表征谱图