(9ci)-5,6-二氢-1H,3h-咪唑并[2,1-c][1,2,4]噻二唑-3-硫酮 | 562075-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (9ci)-5,6-二氢-1H,3h-咪唑并[2,1-c][1,2,4]噻二唑-3-硫酮
• 英文名称: 6,7-dihydro-5H-imidazo[2,1-c][1,2,4]thiadiazol-3-thione
• 英文别名: 1H,3H-Imidazo[2,1-c][1,2,4]thiadiazole-3-thione, 5,6-dihydro-；6,7-dihydro-5H-imidazo[2,1-c][1,2,4]thiadiazole-3-thione
• CAS: 562075-34-7
• 化学式: C₄H₅N₃S₂
• 分子量: 159.236
• InChiKey: GCHCAFIIXGRBLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-三氟甲基苯磺酰氯 、 (9ci)-5,6-二氢-1H,3h-咪唑并[2,1-c][1,2,4]噻二唑-3-硫酮 在 吡啶 作用下， 反应 12.0h， 以48%的产率得到N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)-thiocarbonyl]-2-imidazolidene}-4-trifluoromethylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and in vitro anti-tumor activity of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides

  摘要：

  A series of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides (2a-z) was obtained by reacting 6,7-dihydro-1H-imidazo[2,1-c][1,2,4]thiadiazol-3-thione (1) with arylsulfonyl chlorides. The relationships between structure and anti-tumor activity revealed that compound 2o with p-Cl substituent at the phenyl ring was most active (-log GI50 > 8.00, -log TGI = 7.66) and was found to exhibit high selectivity toward the leukemia CCRF-CEM cell line (Delta(f) = 3.08 and 3.31, respectively). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.067
• 作为产物：
  描述：

  N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)-thiocarbonyl]-2-imidazolidene}phenylsulfonamide 在 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以50%的产率得到bis{[2-(phenylsulfonylimino)imidazolidin-1-yl]thiocarbonyl} disulfide
  参考文献：
  名称：

  Synthesis, X-ray structure analysis and computational studies of novel bis(thiocarbamoyl) disulfides with non-covalent S⋯N and S⋯S interactions

  摘要：

  In this Letter, we describe the synthesis of several bis(thiocarbamoyl) disulfides that present interesting intramolecular S center dot center dot center dot N and S center dot center dot center dot S interactions. In one case, crystals suitable for X-ray characterization have been obtained. The non-covalent interactions have been studied analyzing the crystal structure and by means of high level density functional theory (DFT) calculations (RI-PB86/TZVP) using both 'atoms-in-molecules' (AIM) and natural bond orbital (NBO) analyses. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2006.02.022

文献信息

• Synthesis, Molecular Structure, and Applications of 2-Hydroxylamino-4,5-dihydroimidazolium-<i>O</i>-sulfonate to the Synthesis of Novel Heterocyclic Ring Systems
  作者：Franciszek Sa̧czewski、Jarosław Sa̧czewski、Maria Gdaniec

  DOI：10.1021/jo034309n

  日期：2003.6.1

  2-hydroxylamino-4,5-dihydroimidazolium-O-sulfonate (1) has been prepared by reacting 2-chloro-4,5-dihydroimidazole with hydroxylamine-O-sulfonic acid. Deprotonated compound 1a containing both the nucleophilic endocyclic nitrogen atoms and electrophilic exocyclic nitrogen was used for the syntheses of 3-substituted 6,7-dihydro-5H-imidazo[2,1-c][1,2,4]oxadiazoles 2-9 and 6,7-dihydro-5H-imidazo[2,1-c][1

  通过使2-氯-4，5-二氢咪唑与羟胺-O-磺酸反应来制备2-羟基氨基-4，5-二氢咪唑-O-磺酸盐（1）。使用含有亲核性内环氮原子和亲电性环外氮原子的去质子化化合物1a来合成3取代的6,7-二氢-5H-咪唑并[2,1-c] [1,2,4]恶二唑2-9通过串联亲核加成-亲电胺化反应得到6,7-二氢-5H-咪唑并[2,1-c] [1,2,4]噻二唑-3-硫酮（10）。该方法有望用于合成多种其他杂环。另一方面，通往7,8-二氢咪唑并[1,2-c] [1,3,5]噻二嗪-2,4（6H）-二硫酮（16）和2,6,7,8-从化合物1开始报道了四氢咪唑并[1,2-a] [1,3,5]三嗪-4（3H）-硫酮衍生物（17）。

表征谱图