5-氨基-3-硫代氧基-3H-(1,2)二硫杂环戊烯-4-甲腈 | 5147-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 中文名称: 5-氨基-3-硫代氧基-3H-(1,2)二硫杂环戊烯-4-甲腈
• 中文别名: 3-氨基-5-硫代-4-二硫杂环戊二烯甲腈；5-氨基-3-硫代-3H-1,2-二硫杂环戊二烯-4-甲腈；3-氨基-5-硫基亚甲基-1,2-二硫杂环戊二烯-4-甲腈；3-氨基-5-硫基亚甲基二硫杂环戊二烯-4-甲腈；3-氨基-5-硫代-二硫杂环戊二烯-4-甲腈
• 英文名称: 3-Amino-5-thiono-1,2-dithiol-4-carbonitril
• 英文别名: 5-Amino-3-thioxo-3H-dithiol-4-carbonitril；5-amino-3-thioxo-3H-1,2-dithiole-4-carbonitrile；4-Cyano-5-amino-1,2-dithiol-3-thion；5-Amino-4-cyano-1,2-dithiolthion-(3)；5-amino-4-cyano-3H-1,2-dithiole-3-thione；4-Cyano-5-amino-trithion；3-amino-5-sulfanylidenedithiole-4-carbonitrile
• CAS: 5147-74-0
• 化学式: C₄H₂N₂S₃
• mdl: MFCD00607130
• 分子量: 174.271
• InChiKey: IXPKEXWZTKXQBC-UHFFFAOYSA-N

物化性质

• 熔点：
  >360°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  5-氨基-3-硫代氧基-3H-(1,2)二硫杂环戊烯-4-甲腈 、 乙酸酐 在 吡啶 作用下， 反应 3.5h， 以30%的产率得到N-(4-cyano-3-thioxo-3H-1,2-dithiol-5-yl)acetamide
  参考文献：
  名称：

  Syntheses and Structure Study on 3,3aλ4,4-Trithia-1-azapentalenes and Their 3-Oxa Analogues

  摘要：

  翻译结果： 研究了5-氨基-3-硫代-3H-1,2-二硫杂环-4-羧酸的腈、酰胺或酯1与烷基化和酰化试剂的反应。以几种方式形成了“离子”1,2-二硫杂环酰胺6。用五硫化二磷处理得到相应的3,3aλ4,4-三硫杂-1-氮杂五环7。利用X射线分析、红外光谱和HF和DFT量子化学计算相结合的方法研究了合成的杂环的结构。

  DOI：

  10.1135/cccc20031243
• 作为产物：
  描述：

  5-Amino-3-thioxo-3H-dithiol-4-thiocarboxamid 在 甲酸 作用下， 反应 2.0h， 生成 5-氨基-3-硫代氧基-3H-(1,2)二硫杂环戊烯-4-甲腈
  参考文献：
  名称：

  Gewald, K.; Schindler, R., Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 2, p. 223 - 228

  摘要：

  DOI：

文献信息

• Transformation of 1,2-Dithiole-3-thiones Into 1,6,6aλ4-Trithiapentalenes via Reaction with Bromoethanones
  作者：Richard Čmelík、Pavel Pazdera

  DOI：10.1135/cccc20060650

  日期：——

  We report the reactions of derivatives of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid 1 with bromoethanones and acylation agents. Two different routes were used to obtain the products, 3-(acylmethylidene)-3H-1,2-dithioles 4. These compounds were synthesized by acylation of compounds 1 on the amino group, followed by the reaction with bromoethanones and excess of triethylamine. Another method was based on the inverted order of the mentioned reaction steps and in absence of a base. The treatment of 4 with thionyl chloride gave new unsaturated fused lactones 13 whereas thionation led to desired 1,6,6aλ⁴-trithiapentalenes 5. The structures of products and the reaction mechanisms are discussed.

  我们报告了5-氨基-3-硫代-3H-1,2-二硫杂环-4-羧酸衍生物1与溴乙酮和酰化试剂的反应。使用两种不同的途径获得产物3-(酰基甲基亚)-3H-1,2-二硫杂环4。这些化合物是通过在氨基上酰化化合物1，然后与溴乙酮和过量三乙胺反应合成的。另一种方法基于所述反应步骤的倒置顺序，在没有碱的情况下进行。用亚磺酰氯处理4得到新的不饱和融合内酯13，而用亚磺化反应则得到所需的1,6,6aλ4-三硫杂戊烯5。讨论了产物的结构和反应机理。
• REGIOSELECTIVITY OF ELECTROPHILIC ATTACKS TO 5-AMINO-3-THIOXO-3H-1,2-DITHIOLE-4-CARBOXYLIC ACID FUNCTIONAL DERIVATIVES. ELUCIDATION OF PRODUCT STRUCTURES.
  作者：Richard Čmelík、Jaromír Marek、Pavel Pazdera

  DOI：10.1515/hc.2002.8.1.55

  日期：2002.1

  An acylation of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid functional derivatives led to the formation of N-acyl compound via S-acyl intermediate. On the other hand, alkylation occurred only at the sulfur atom of thioxo group. Structure elucidation of both types of products was done by IR, 1H, 13C NMR and X-ray structural analysis.

  5-氨基-3-硫代-3H-1,2-二硫醇-4-羧酸官能衍生物的酰化导致通过 S-酰基中间体形成 N-酰基化合物。另一方面，烷基化仅发生在硫代基团的硫原子上。通过IR、1H、13C NMR和X射线结构分析对两种类型的产物进行结构解析。
• Reactivity of 3H-1,2,4-dithiazole-3-thiones and 3H-1,2-dithiole-3-thiones as sulfurizing agents for oligonucleotide synthesis
  作者：Andrei P. Guzaev

  DOI：10.1016/j.tetlet.2010.11.086

  日期：2011.1

  The reactivity of 5-amino-3H-1,2,4-dithiazole-3-thiones substituted at their amino group and 5-amino-3H-1,2-dithiole-3-thiones substituted at their amino group and C4 toward compounds containing P(III) atoms has been studied. N,N-Disubstituted-N'-(3-thioxo-3H-1,2,4-dithiazol-5-yl)methanimidamides were selected as novel efficient sulfur transfer reagents suitable for DNA and RNA synthesis. (C) 2010 Elsevier Ltd. All rights reserved.
• Amino-thieno[2,3-c]pyrazole und Amino-thieno[2,3-b]pyrrole
  作者：K. Gewald、S. Rennert、R. Schindler、H. Sch�fer

  DOI：10.1002/prac.199533701101

  日期：——

  The synthesis of thieno[2,3-c]pyrazoles and thieno [2,3-b]pyrroles is described. From the dithioliumsalt (1) and potassium hydroxide the potassium-(2,2-dicyan-1-methylthio-ethen-1-yl)-thiolate (2) is formed. This reacts with hydrazine hydrate to form the 3-amino-5-thioxo-pyrazol-4-carbonitrile (3). S-Alkylation with alpha-chlorocarbonyl compounds yielding (6a-c) leads via Thorpe-Ziegler-cyclization to 3,4-diamino-thieno[2,3-c]pyrazoles (9) if the position 1 is alkylated (8). Acetyl acetone yields 2-mercapto-pyrazolo[1,5-a]pyrimidine (5). After S-alkylation (10a-d) are immediately cyclized to thieno [2',3':3,4]pyrazolo[1,5-a]pyrimidine (11a-d). The ketone (6a) can be cyclized to the pyrazolo [5,1-b]thiazole (12). 3 reacts with oxalyl chloride to form the 2,3-dioxo-6-thioxo-imidazo[1,2-b]pyrazole (13) of which S-phenacyl derivative (14) because the NH-proton cannot be cyclized. The 5-amino-3,4-dicyano-pyrrol-2-thiolate (16) shows the analogous behaviour. The S-alkylation is followed by cyclization, and 3,5-diamino-thieno[2,3-b]pyrroles (18a-b) arise. Reaction of 5-amino-2-alkylthio-pyrrol-3,5-dicarbonitrile (17) with acetyl acetone provides pyrrolo[1,2-a]pyrimidine (20a-c) which can be cyclized to form thieno[3',2':4,6]pyrimidines (21a-c) very easily.
• One-pot synthesis, structure, theoretical study and vibrational spectroscopy of 5-amino-4-cyano-3H-1,2-dithiole-3-thione
  作者：Yanning Cao、Hanhui Zhang、Yiji Lin、Changcang Huang、Yiping Chen、Fengli Zhang、Jianshan Chen

  DOI：10.1016/j.molstruc.2007.12.034

  日期：2008.10

  A novel D3T derivative, 5-amino-4-cyano-3H-1,2-dithiole-3-thione (compound 1) has been obtained in one-pot reaction. The crystal is orthorhombic, space group Pbca, with a = 10.3667(4) angstrom, b = 10.8898(4) angstrom, c = 11.4942(5) angstrom, V = 1297.60(9)angstrom(3), and Z = 8. In the crystal, molecules are firstly self-assembled into a complex sheet parallel to the (00 1) plane containing centrosymmetric R-2(4) (16) and R-4(4) (24) rings, and then the interconnection of molecular sheets through S center dot center dot center dot S interactions forms a three-dimensional supramolecular assembly. The DFT calculations are performed for isolated molecule using the B3LYP/6-31+G(d,p) methods. The frontier orbital properties of compound I have been reported and discussed. Moreover, a detailed assignment of the fundamental vibrational modes is proposed on the basis of the calculated results. (C) 2008 Elsevier B.V. All rights reserved.