5-[(4-nitrobenzyl)sulfanyl]-1-phenyl-1H-tetrazole | 81645-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[(4-nitrobenzyl)sulfanyl]-1-phenyl-1H-tetrazole
• 英文别名: 5-(4-nitrobenzylthio)-1-phenyl-1H-tetrazole；5-(4-nitrobenzylthio)-1-phenyltetrazole；1-phenyl-5-(4-nitrobenzyl)-thio-1H-tetrazole；1-phenyl-5-(p-nitrobenzylthio)tetrazole；1H-Tetrazole, 5-[[(4-nitrophenyl)methyl]thio]-1-phenyl-；5-[(4-nitrophenyl)methylsulfanyl]-1-phenyltetrazole
• CAS: 81645-83-2
• 化学式: C₁₄H₁₁N₅O₂S
• mdl: MFCD00991851
• 分子量: 313.34
• InChiKey: XINSQOLXINNYJA-UHFFFAOYSA-N

物化性质

• 沸点：
  547.8±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对硝基溴化苄 在 氮 作用下， 以 乙醇 、 1-苯基-5-巯基四氮唑 为溶剂， 生成 5-[(4-nitrobenzyl)sulfanyl]-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Phenylmercaptotetrazolo- and nitroindazolo masked development/image

  摘要：

  新型硝基苄基化合物被加入到感光乳剂或显影剂中，用于控制显影/图像修饰化合物的释放。这种释放仅在显影过程中形成显影剂氧化产物后，按图像的方式发生。例如，硝基苄基掩蔽的苯硫基四唑（PMT），被掺入到卤化银乳剂中，通过与显影剂氧化产物的电子转移机制反应，释放出强大的显影抑制剂PMT。

  公开号：

  US04501896A1

文献信息

• Direct Synthesis of Thioethers from Carboxylates and Thiols Catalyzed by FeCl₃
  作者：Kunuru Venkatesham、Chitturi Bhujanga Rao、Chanti Babu Dokuburra、Richard A. Bunce、Yenamandra Venkateswarlu

  DOI：10.1021/acs.joc.5b02143

  日期：2015.11.20

  A new and efficient method has been developed for the synthesis of thioethers from carboxylates and thiols. The reaction proceeds via a Fe(III)-catalyzed direct displacement of carboxylates from benzylic or allylic esters by heterocyclic thiols. Short reaction times, good to excellent yields of products, and few side reactions are the significant features of the new protocol.

  已经开发了一种新的有效方法，用于从羧酸盐和硫醇合成硫醚。该反应通过杂环硫醇通过Fe（III）催化的羧酸酯从苄基或烯丙基酯直接置换而进行。新协议的显着特点是反应时间短，产品收率好至极好，副反应少。
• Cytostatic tetrazole–butenolide conjugates: linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances
  作者：Vojtěch Balšánek、Lucie Tichotová、Jiří Kuneš、Marcel Špulák、Milan Pour、Ivan Votruba、Vladimír Buchta

  DOI：10.1135/cccc2009040

  日期：——

  A series of tetrazoles linked to the butenolide core via benzene rings were prepared by the Stille coupling reaction of α-(tributylstannyl)butenolides and 5-(alkylsulfanyl)-1-(4-iodophenyl)tetrazoles, and the compounds were tested for antifungal and cytostatic activity. Interesting antifungal activities against the filamentous strain Absidia corymbifera, and cytostatic activities against leukemic cells HL-60 and CCRF-CEM were found. The cytostatic activity requires the presence of both the butenolide ring and the alkylsulfanyl group bound to tetrazole ring. In addition, the feasibility of Pd-coupling reactions with 5-iodotetrazoles was evaluated.

  一系列通过苯环连接到丁烯内酯核心的四唑类化合物，是通过α-(三丁基锡基)丁烯内酯和5-(烷基硫基)-1-(4-碘苯基)四唑的斯蒂尔偶联反应制备的，并且对这些化合物进行了抗真菌和细胞毒活性测试。有趣的抗真菌活性针对丝状菌株Absidia corymbifera，以及对白血病细胞HL-60和CCRF-CEM的细胞毒活性被发现。细胞毒活性需要丁烯内酯环和连接到四唑环的烷基硫基团同时存在。此外，还评估了与5-碘四唑进行Pd偶联反应的可行性。
• Preparation of thioethers
  申请人：Gist-Brocades N.V.

  公开号：US04496720A1

  公开（公告）日：1985-01-29

  A novel process for the preparation of thioethers comprising reacting a silylated thiol of the formula R--S--SiR.sub.1 R.sub.2 R.sub.3 I wherein R is an organic group and R.sub.1, R.sub.2 and R.sub.3 are individually selected from the group consisting of alkyl of 1 to 4 carbon atoms with an organic halide, sulfate or sulfonate in the presence of hexamethylphosphoric triamide as a solvent or co-solvent preferably under neutral conditions in aprotic solvents at a temperature between 0.degree. and 150.degree. C.

  一种新型的制备硫醚的方法，包括将具有化学式R--S--SiR.sub.1 R.sub.2 R.sub.3 I的硅烷基硫醇与有机卤化物、硫酸酯或磺酸酯在六甲基膦酸三胺存在下反应，其中R为有机基，R.sub.1、R.sub.2和R.sub.3分别选自1至4个碳原子的烷基，最好在无极性溶剂中在0度至150度之间的中性条件下进行。
• Masked antifoggant compounds for silver photographic systems
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0045129A2

  公开（公告）日：1982-02-03

  Novel benzyl compounds are provided with nuclear substituents such that a net electron withdrawing effect occurs at the a-carbon atom of the benzyl structure, the α-carbon atom being substituted by a radical which, upon release during a photographic process, forms a photographically active antifoggant, toner, spectral sensitizer, dye, color coupler, silver halide solvent, stabilizer, hardener or accelerator. When incorporated into a photographic emulsion or developer the compounds provide controlled imagewise release of development/ image modifier compounds after developer oxidation products have been formed in the course of the development process. For example, nitrobenzyl-masked phenylmercaptotetrazole (PMT), incorporated into a silver halide emulsion, reacts with developer oxidation products via an electron transfer mechanism to release the potent development restrainer PMT.

  新型苄基化合物具有核取代基，从而在苄基结构的 a 碳原子上产生净电子撤回效应，α 碳原子被自由基取代，在照相过程中释放后，形成具有照相活性的防雾剂、调色剂、光谱感光剂、染料、色彩耦合剂、卤化银溶剂、稳定剂、硬化剂或促进剂。当这些化合物加入感光乳剂或显影剂中时，可以在显影过程中形成显影剂氧化产物后，控制显影/图像修饰化合物的图像释放。例如，加入卤化银乳剂中的硝基苄基掩蔽苯基巯基四唑（PMT）通过电子转移机制与显影剂氧化产物发生反应，释放出强效显影抑制剂 PMT。
• Process for the preparation of thioethers
  申请人：GIST-BROCADES N.V.

  公开号：EP0088831A1

  公开（公告）日：1983-09-21

  Process for the preparation of thioethers by reacting a silylated thiol of the general formula: wherein R represents an organic group and R1, R2 and R3 are the same or different and each represents an alkyl group having 1 to 4 carbon atoms, with an organic halide, sulphate or sulphonate in the presence of hexamethylphosphoric triamide as a solvent or co-solvent. The process is carried out under neutral conditions in aprotic solvents at a temperature between 0° and 150°C.

  通式为：其中 R 代表有机基团，R1、R2 和 R3 相同或不同，且各自代表具有 1 至 4 个碳原子的烷基的硅烷化硫醇与有机卤化物、硫酸盐或磺酸盐在作为溶剂或助溶剂的六甲基磷酸三酰胺存在下反应制备硫醚的工艺。 该工艺在中性条件下，在温度为 0° 至 150°C 的钝溶剂中进行。