3-pyridyldithiocarbazoic acid methyl ester | 28540-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-pyridyldithiocarbazoic acid methyl ester
• 英文别名: Methyl-3-nicotinoyldithiocarbazate；methyl 2-nicotinoylhydrazinecarbodithioate；N'-nicotinoyl-hydrazinecarbodithioic acid methyl ester；Methyl 2-(pyridin-3-ylcarbonyl)hydrazinecarbodithioate；methyl N-(pyridine-3-carbonylamino)carbamodithioate
• CAS: 28540-05-8
• 化学式: C₈H₉N₃OS₂
• 分子量: 227.311
• InChiKey: LKKJKTWNFOYEPP-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162 °C(Solv: methanol (67-56-1))
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-pyridyldithiocarbazoic acid methyl ester 在 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以47%的产率得到3-(5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-pyridine
  参考文献：
  名称：

  ZnCl2 catalyzed efficient synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole

  摘要：

  New methods for the synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole have been described. No cyclizations took place in the absence of ZnCl2. 1,3,4-Thiadiazoles are formed in the presence of ZnCl2 alone, whereas oxadiazoles are produced when a base such as Et3N or KOH was used along with ZnCl2. % Yields are optimized. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.046
• 作为产物：
  描述：

  二硫化碳 、 3-吡啶甲酰肼 、 碘甲烷 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以70%的产率得到3-pyridyldithiocarbazoic acid methyl ester
  参考文献：
  名称：

  New Method of 4,5-Disubstituted 1,2,4-triazolo-3-thiones Synthesis

  摘要：

  A universal method of 4,5-disubstituted S-triazolo-3-thiones synthesis from methyl esters of arylothiocarbazoic acids and some primary amines is presented.

  DOI：

  10.1080/104265090508217

文献信息

• Synthesis and Tuberculostatic Activity of Novel 1,2,4-Triazoles Obtained from Heterocyclic Carbohydrazides
  作者：Katarzyna Gobis、Henryk Foks、Zofia Zwolska、Ewa Augustynowicz-Kopeć

  DOI：10.3987/com-09-11888

  日期：——

  The novel 1,2,4-triazole derivatives have been synthesized by a few different pathways. Heterocyclic carbohydrazides were used to obtain monoesters of hydrazine acids (1-6), thiosemicarbazide derivatives (7-17), and finaly 1,2,4-triazole-5-thiones (18-38). Carbohydrazides were also cyclized with methyl carbamodithioates in the presence of DBU giving 1,2,4-triazole-5-thiones (18, 19, 39-47). Two of final products (39, 40) were undergone alkylation in alkaline solution to appropriate sulfides (48-53). Then methylsulfides (48, 49) were oxidized with peroxyacetic acid to sulfoxides (54, 55). The obtained compounds were tested in vitro towards Mycobacterium tuberculosis.
• New Method of 4,5-Disubstituted 1,2,4-triazolo-3-thiones Synthesis
  作者：Henryk Foks、Barbara Milczarska

  DOI：10.1080/104265090508217

  日期：2005.1.1

  A universal method of 4,5-disubstituted S-triazolo-3-thiones synthesis from methyl esters of arylothiocarbazoic acids and some primary amines is presented.
• ZnCl2 catalyzed efficient synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole
  作者：Md.A. Rahman、Mohammad R. Karim、Md. Arifuzzaman、Tasneem A. Siddiquee、Aminul H. Mirza

  DOI：10.1016/j.tetlet.2014.04.046

  日期：2014.5

  New methods for the synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole have been described. No cyclizations took place in the absence of ZnCl2. 1,3,4-Thiadiazoles are formed in the presence of ZnCl2 alone, whereas oxadiazoles are produced when a base such as Et3N or KOH was used along with ZnCl2. % Yields are optimized. (C) 2014 Elsevier Ltd. All rights reserved.