2-(4-nitrophenyl)-1,3,4-thiadiazole-5-carbonitrile

• 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: 2-(4-nitrophenyl)-1,3,4-thiadiazole-5-carbonitrile
• 英文别名: 5-(4-Nitrophenyl)-1,3,4-thiadiazole-2-carbonitrile
• 化学式: C₉H₄N₄O₂S
• 分子量: 232.222
• InChiKey: DGMXJGPRIOHCOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对硝基苯甲腈 在 叠氮阴离子 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-(4-nitrophenyl)-1,3,4-thiadiazole-5-carbonitrile
  参考文献：
  名称：

  From tetrazoles via hydrazonoyl chlorides to 1,3,4-thiadiazole oligomers

  摘要：

  5-Substituted tetrazoles react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides (14) in high yield. 5-Aminotetrazole reacts further to give an extended bis-imine (6) which, with triphenylphosphine at room temperature, rapidly gives 1,3,4-thiadiazoles 15 and 17. The mono-imines 14 react similarly to give simpler thiadiazoles 18 in high yield. By repetition of the tetrazole formation and Appel salt-triphenylphosphine sequence, these 2-cyanothiadiazoles 18 are converted in high yield into thiadiazole dimers and trimers 21, n=1 and 2. These reactions are explained mechanistically. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01505-7

文献信息

• Synthesis of 1,3,4-thiadiazole oligomers
  作者：Van-Duc Le、Charles W. Rees、Sivaprasad Sivadasan

  DOI：10.1039/b203705j

  日期：2002.6.27

  A range of hydrazono chlorides 8, readily prepared from 5-substituted tetrazoles 7 and Appel salt 1, are rapidly converted by triphenylphosphine into 5-cyano-1,3,4-thiadiazoles 9 in high yield. These cyanides are converted by azide into the corresponding tetrazoles 10 which with Appel salt give the hydrazono chlorides 11 which are similarly converted by triphenylphosphine into the bi-1,3,4-thiadiazolyls 12a,c,g, all in high yield. Repetition of the 3-step sequence (12 → 13 → 14 → 15) gives the ter-1,3,4-thiadiazolyls 15a,g.

  由 5-取代的四唑 7 和阿贝尔盐 1 很容易制备出一系列肼基氯化物 8，这些肼基氯化物在三苯基膦的作用下迅速转化为 5-氰基-1,3,4-噻二唑 9，产量很高。这些氰化物被叠氮化物转化为相应的四唑 10，与阿佩尔盐一起生成肼基氯化物 11，这些肼基氯化物 11 同样被三苯基膦转化为双-1,3,4-噻二唑 12a,c,g，产量都很高。重复 3 步顺序（12 → 13 → 14 → 15），可得到 1,3,4-噻二唑三醇 15a,g。
• From tetrazoles via hydrazonoyl chlorides to 1,3,4-thiadiazole oligomers
  作者：Van-Duc Le、Charles W Rees、Sivaprasad Sivadasan

  DOI：10.1016/s0040-4039(00)01505-7

  日期：2000.12

  5-Substituted tetrazoles react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides (14) in high yield. 5-Aminotetrazole reacts further to give an extended bis-imine (6) which, with triphenylphosphine at room temperature, rapidly gives 1,3,4-thiadiazoles 15 and 17. The mono-imines 14 react similarly to give simpler thiadiazoles 18 in high yield. By repetition of the tetrazole formation and Appel salt-triphenylphosphine sequence, these 2-cyanothiadiazoles 18 are converted in high yield into thiadiazole dimers and trimers 21, n=1 and 2. These reactions are explained mechanistically. (C) 2000 Elsevier Science Ltd. All rights reserved.