3,4-二氨基噻吩并[2,3-b]噻吩-2,5-二羧酸二乙酯 | 4004-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 中文名称: 3,4-二氨基噻吩并[2,3-b]噻吩-2,5-二羧酸二乙酯
• 英文名称: Diethyl 3,4-diaminothieno<2,3-b>thiophene-2,5-dicarboxylate
• 英文别名: diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate；3,4-diamino-2,5-dicarbethoxy-thieno(2,3-b)thiophene；3,4-diamino-2,5-dicarbethoxythieno(2,3-b)thiophene；3,4-diamino-2,5-dicarbethoxythieno[2,3-b]thiophene；3,4-diamino-2,5-dicarbetoxythieno(2,3-b)thiophene；3,4-diamino-thieno[2,3-b]thiophene-2,5-dicarboxylic acid diethyl ester
• CAS: 4004-20-0
• 化学式: C₁₂H₁₄N₂O₄S₂
• 分子量: 314.386
• InChiKey: FTGFURZVTLYXEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3,4-二氨基噻吩并[2,3-b]噻吩-2,5-二羧酸二乙酯 在 sodium hydroxide 作用下， 生成 3,4-diaminothieno(2,3-b)thiophene-2,5-dicarboxylic acid
  参考文献：
  名称：

  SYNTHESIS OF POLYFUSED THIEN0(2,3-b)THIOPHENES PART 2: SYNTHESIS OF THIENOPYRIMIDINE, THIENOTHIAZINE, THIENOPYRROLOPIPRAZINE, AND THIENOTHIAZAPHOSPHOLINE DERIVATIVES

  摘要：

  3,4-Diamino-2,5-dicarbethoxythieno(2,3-(b) under bar )thiophene (1) was reacted with triethylorthoformate to afford compound 2. The reaction of compounds 2 or 3 with S.S-acetals and N,S-acetals, afforded compounds 4-6. Treatment of compound 1 with 2,5 -dimethoxytetrahydrofuran gave the corresponding bipyrrolyl derivative 7, which was reacted with hydrazine hydrate to get the corresponding hydrazide derivative 8. Treating compound 8 with sodium nitrite afforded the corresponding carboazide derivative 9, which in rum cyclized to compound 10. Compound 12 was obtained via the reaction of compound 1 with PhNCS or through treating compound 11 with CS2 PhNH2, and KOH. Also, compound 13 was prepared through treatment of compound 12 wi;h Lawesson's reagent or via the reaction of compound 11 with CS2 followed by treating the resulting compound 14 with PhNH2. The reaction of compounds 1 or 3 with Lawesson's reagent gave compound 15. Benzoylation of compound 1 afforded compound 16, which treated with NH3 gave compound 17. Treatment of compounds 16 or 17 with LR furnished compounds 18 or 19, respectively. The reaction of compound 16 or 17 with P2S5 yielded compounds 19 and 20 or 18 and 19, respectively.

  DOI：

  10.1080/10426500008076530
• 作为产物：
  描述：

  ethyl 3-amino-4-cyano-5-((2-ethoxy-2-oxoethyl)thio)thiophene-2-carboxylate 在 sodium ethanolate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到3,4-二氨基噻吩并[2,3-b]噻吩-2,5-二羧酸二乙酯
  参考文献：
  名称：

  新亚氨基膦烷介导的噻吩并[3'，2'：4,5]噻吩并[3,2 - d ]嘧啶-4（3 H）-ones和5 H -2,3-dithia-5,7- diaza的合成-环戊[ c，d ]茚

  摘要：

  由3，4-二氨基噻吩并[2，3- b ]噻吩3与过量的三苯基膦，C 2 Cl 6和Et 3 N的反应由于分子内双氢键的形成而选择性地制备了单（亚氨基膦烷）4。单（亚氨基磷烷）4与芳族异氰酸酯反应生成稳定的碳二亚胺8，将其进一步用脂肪族仲或伯胺处理，得到2-氨基取代的噻吩并[3'，2'：4,5]噻吩并[3,2- d催化量的EtO - Na存在下] pyrimidin-4（3 H）-ones 10或12+。然而，在催化量的碳酸钾存在下，碳二亚胺8通过直接环化以高收率转化成先前未报道的5 H -2,3-二硫-5,7-二氮杂-环戊烯[ c，d ]茚满13。碳二亚胺8与苯酚在催化量的碳酸钾存在下的反应得到2-芳氧基取代的噻吩并[3'，2'：4,5]噻吩并[3,2 - d ]嘧啶-4（3）的混合物H）-14和13。10m的X射线结构分析证明了氨基的结构和拟议的反应性。

  DOI：

  10.1016/j.tet.2008.07.036

文献信息

• Novel Synthesis of Condensed Pyridin-2(1H)-one and Pyrimidine Derivatives
  作者：A. M. M. Soliman、A. Khodairy、E. A. Ahmed

  DOI：10.1080/10426500307793

  日期：2003.4

  The reaction of N-chloroacetyl derivatives 6-10 with morpholine yielded N-morpholin-1-yl acetyl derivatives 11-15 , which were subjected to Thorpe-Zieler cyclization with sodium tert -butoxide to produce the corresponding condensed pyridin-2(1H)-one derivatives 16-20 . Treatment of compounds 1 , 6-10 with either malononitrile or p -chlorobenzylidinemalononitrile in presence of triethylamine, afforded

  N-氯乙酰基衍生物 6-10 与吗啉反应生成 N-morpholin-1-yl 乙酰基衍生物 11-15 ，将其与叔丁醇钠进行 Thorpe-Zieler 环化反应生成相应的缩合吡啶-2(1H) -一衍生物16-20。在三乙胺存在下用丙二腈或对氯苄基丙二腈处理化合物1、6-10，分别得到相应的嘧啶21-25、27和吡啶衍生物26。此外，用异硫氰基乙酸乙酯处理化合物1a，得到相应的哌嗪衍生物28。
• Utility of [4‐(3‐methoxyphenyl)pyrimidin‐2‐yl]cyanamide in synthesis of some heterocyclic compounds
  作者：Bahgat R. M. Hussein、Ahmed Khodairy

  DOI：10.1002/jhet.4324

  日期：2021.10

  N-[4-(3-Methoxyphenyl)pyrimidin-2-yl]cyanamide (1) was reacted with morpholine and respective binuclephilic reagents namely: ethylenediamine, o-phenylenediamine, o-aminothiophenol, or o-aminophenol to give the corresponding carboximidamide 2, imidazolidine 3, and benzazoles 4–6. While its reaction with hydrazides in DMF at 90°C, gave the corresponding 1,2,4-triazols 7–11. Also, treatment of cyanamide

  ñ - [4-（3-甲氧基苯基）嘧啶-2-基]氰胺（1）与吗啉和相应的试剂binuclephilic即进行反应：乙二胺，Ó苯二胺，Ò -aminothiophenol，或ö氨基苯酚，得到相应的甲脒2、咪唑烷3和苯并唑4–6。在 90°C 下，它在 DMF 中与酰肼反应，得到相应的 1,2,4-三唑7-11。此外，治疗氰胺1与具有亲核和亲电基团（─NH杂环2中/─COOEt）异-丙醇存在催化量的浓度。HCl，分别得到相应的噻吩并[2,3- d ]嘧啶酮12和意外的噻吩并[3,2- d ]嘧啶13，而不是双-噻吩并[3,2- d ]嘧啶14。同时，它与 5-氨基-1,3-噻唑-4-羧酸乙酯的反应产生了意想不到的N- (嘧啶-2-基)脲15而不是相应的噻唑并[5,4- d ]嘧啶16。意想不到ñ -硫脲（嘧啶-2-基）17获得，当氰胺1与硫醇钾在异丙醇中与催化量的 Conc 反应。盐酸。
• Phenyl Groups Result in the Highest Benzene Storage and Most Efficient Desulfurization in a Series of Isostructural Metal-Organic Frameworks
  作者：Wen-Wen He、Guang-Sheng Yang、Yu-Jia Tang、Shun-Li Li、Shu-Ran Zhang、Zhong-Min Su、Ya-Qian Lan

  DOI：10.1002/chem.201500815

  日期：2015.6.26

  A series of isoreticular metal–organic frameworks (MOFs; NENU‐511–NENU‐514), which all have high surface areas and strong adsorption capacities, have been successfully constructed by using mixed ligands. NENU‐513 has the highest benzene capacity of 1687 mg g−1at 298 K, which ranks as the top MOF material among those reported up to now. This NENU series has been used for adsorptive desulfurization because

  使用混合配体已成功构建了一系列具有高表面积和强吸附能力的等孔金属有机骨架（MOF；NENU‐511 – NENU‐514）。NENU‐513在298 K时的最高苯容量为1687 mg g -1，在迄今为止报道的那些中，它是MOF的首屈一指的材料。由于其永久的孔隙率，该NENU系列已被用于吸附脱硫。结果表明，与其他MOF材料（尤其是NENU-511）相比，该系列在去除有机硫化合物方面具有更高的吸附效率。，它在周围大气中具有最高的吸附效率。这项研究证明，具有较高表面积和官能团的目标MOF的设计和合成是提高苯存储能力和有机硫化合物吸附的有效方法。
• Synthesis of Polyfused Thieno(2,3- b )thiophenes Part 3: Synthesis of Thienopyrimidinotetrazole, Thienopyrimidinotriazepine, Thienopyrimidinotriazine, Thienopyrimidinotriazole and Pyrazolylthienopyrimidine Derivatives
  作者：A. Khodairy

  DOI：10.1080/10426500307790

  日期：2003.4

  2,9-Dihydrazinobipyrimidino(2,3- b )thienothiophene ( 2 ) was reacted with nitrous acid, ethoxymethylenemalononitrile, bromomalononitrile, triethyl formate, CS 2 or isatine to afford the corresponding tetrazole, triazepine, triazine, and triazole derivatives 3-8 respectively. Treatment of compound 2 with cyclohexylidenenitriles, acetylacetone, ethyl acetoacetate, 2-hydroxyacetophenone, or S,S-acetals

  2,9-二肼基双嘧啶(2,3-b)噻吩并噻吩 (2) 与亚硝酸、乙氧基亚甲基丙二腈、溴丙二腈、甲酸三乙酯、CS 2 或靛红反应，分别得到相应的四唑、三氮杂、三嗪和三唑衍生物 3-8 . 用环己叉腈、乙酰丙酮、乙酰乙酸乙酯、2-羟基苯乙酮或S,S-缩醛处理化合物2分别得到相应的吡唑衍生物9-15。
• Efficient one pot preparation of variously substituted thieno [2,3-<i>b</i>] thiophene
  作者：Alain Cornel、Gilbert Kirsch

  DOI：10.1002/jhet.5570380521

  日期：2001.9

  An efficient one pot access to variously substituted thieno[2,3-b]thiophene is described. The title compounds were obtained from 1,3-dicarbonyl or equivalent compounds, carbon disulfide and halomethyl derivatives in good to high yields and fully characterized.

  描述了一种有效的一锅接触各种取代的噻吩并[2,3- b ]噻吩的方法。由1，3-二羰基或等效化合物，二硫化碳和卤代甲基衍生物以高至高收率获得并充分表征，得到标题化合物。