4-methoxy-2-(1-propynyl)phenyl isocyanate | 315179-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-2-(1-propynyl)phenyl isocyanate
• 英文别名: 1-Isocyanato-4-methoxy-2-prop-1-ynylbenzene
• CAS: 315179-94-3
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: ZSSRXLNEBVPCPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-2-(1-propynyl)phenyl isocyanate 以 苯 为溶剂， 反应 59.0h， 生成 N'-[3-[(9-methoxy-11-methyl-6H-indolo[2,3-b][1,6]naphthyridin-1-yl)amino]propyl]-N'-methylpropane-1,3-diamine
  参考文献：
  名称：

  Synthesis and biological activity of 5-aza-ellipticine derivatives

  摘要：

  Novel 5-aza-ellipticine derivatives were synthesized and tested as antitumor agents. The new compounds were prepared more readily than the analogous ellipticine derivatives, which are known to be potent anti-tumor agents Although the novel 5-aza-ellipticine derivatives are not as biologically active as their corresponding ellipticine analogues, the new compounds represent a new, readily accessible class of heteroaromatic catalytic inhibitors of topoisomerase 11 and possible anti-tumor agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.093
• 作为产物：
  描述：

  4-甲氧基水杨酸甲酯 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 lithium hydroxide 、 copper(l) iodide 、 叠氮磷酸二苯酯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 53.0h， 生成 4-methoxy-2-(1-propynyl)phenyl isocyanate
  参考文献：
  名称：

  Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

  摘要：

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.

  DOI：

  10.1021/jo000978e