5-(氯甲基)-1-苯基-(9ci)-1H-四唑 | 64473-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(氯甲基)-1-苯基-(9ci)-1H-四唑
• 英文名称: 5-(chloromethyl)-1-phenyl-1H-tetrazole
• 英文别名: 5-chloromethyl-1-phenyl-1H-tetrazole；1-phenyl-5-chloromethyltetrazole；5-chloromethyl-1-phenyl-1H-tetrazole；5-Chlormethyl-1-phenyl-1H-tetrazol；5-(chloromethyl)-1-phenyltetrazole
• CAS: 64473-40-1
• 化学式: C₈H₇ClN₄
• mdl: MFCD03854522
• 分子量: 194.623
• InChiKey: KASHDYDHJFKPQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(氯甲基)-1-苯基-(9ci)-1H-四唑 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 6.0h， 生成 5-Ethenyl-1-phenyltetrazole
  参考文献：
  名称：

  Synthesis of vinyl derivatives of tetrazole

  摘要：

  DOI：

  10.1007/bf00505609
• 作为产物：
  描述：

  苯胺 在 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 7.5h， 生成 5-(氯甲基)-1-苯基-(9ci)-1H-四唑
  参考文献：
  名称：

  Improved Potency of Indole-Based NorA Efflux Pump Inhibitors: From Serendipity toward Rational Design and Development

  摘要：

  The NorA efflux pump is a potential drug target for reversal of resistance to selected antibacterial agents, and recently we described indole-based inhibitor candidates. Herein we report a second class of inhibitors derived from them but with significant differences, in shape and size. In particular, compounds 13 and 14 are very potent inhibitors in that they demonstrated, the lowest IC50 values (2 mu M) ever observed among all indole-based compounds we have,evaluated.

  DOI：

  10.1021/acs.jmedchem.6b01281

文献信息

• A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group
  作者：N. T. Pokhodylo、O. Ya. Shyyka、M. D. Obushak

  DOI：10.1134/s1070428020050127

  日期：2020.5

  AbstractA convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

  摘要提出了一种方便的方法，该方法是通过酰胺与三氯氧化磷和叠氮化钠的一锅反应来构建四唑环。获得了一系列含有氨基或羧基的1，5-二取代的四唑，其作为合成生物活性物质的基础材料而受到关注。
• Convergent Three-Component Tetrazole Synthesis
  作者：Ajay L. Chandgude、Alexander Dömling

  DOI：10.1002/ejoc.201600317

  日期：2016.5

  the basis of the availability of the archetypical starting materials, this method provided very versatile synthetic access to 1,5-disubstituted tetrazoles. The usefulness of this method was demonstrated in the synthesis of biologically important fused tetrazole scaffolds and the marketed drug cilostazol.

  开发了一种微波加速、简单、高效的 1,5-四唑支架的构建方法。它包括胺、羧酸衍生物和叠氮化物源的多组分反应。基于原型起始材料的可用性，该方法提供了对 1,5-二取代四唑的非常通用的合成途径。这种方法的实用性在生物学上重要的融合四唑支架和市售药物西洛他唑的合成中得到了证明。
• Transition-metal-free multinitrogenation of amides by C–C bond cleavage: a new approach to tetrazoles
  作者：Lian-Hua Li、Zhi-Jie Niu、Ying-Xiu Li、Yong-Min Liang

  DOI：10.1039/c8cc06324a

  日期：——

  regioselective synthesis of 1,5-disubstituted tetrazoles has been developed. By means of electrophilic amide activation, and further C–C bond cleavage and rearrangement, a diverse set of functionalized 1,5-DST derivatives were selectively constructed under mild conditions. As showcased in the mechanisms, the chemoselectivity is easily switched by the selection of the starting materials in the reaction.

  开发了一种无金属的全新的一锅多酰胺酰胺，用于化学和区域选择性合成1,5-二取代的四唑。通过亲电酰胺的活化，以及进一步的C–C键裂解和重排，在温和条件下选择性地构建了多种功能化的1,5-DST衍生物。如机理所示，通过选择反应中的起始原料可以容易地切换化学选择性。
• Studies on gastric antiulcer active agents. II. Synthesis of tetrazole alkanamides and related compounds.
  作者：Minoru UCHIDA、Makoto KOMATSU、Seiji MORITA、Toshimi KANBE、Kazuyuki NAKAGAWA

  DOI：10.1248/cpb.37.322

  日期：——

  A series of tetrazole alkanamides was synthesized and tested for antiulcer activity against acetic acid-induced gastric ulcer in rats. These compounds were prepared by the reaction of tetrazole alkanoic acids and various amines by the mixed anhydride method or acid chloride method. Among them, 3-[(1-ethyl-5-tetrazolyl)methylthio]propionamide (IIn) was found to have the most potent activity. The structure-activity

  合成了一系列四唑烷酰胺，并测试了其对乙酸诱导的大鼠胃溃疡的抗溃疡活性。这些化合物是通过四唑链烷酸与各种胺通过混合酸酐法或酰氯法反应制得的。其中，发现3-[（（1-乙基-5-四唑基）甲硫基]丙酰胺（IIn）具有最强的活性。讨论了构效关系。
• Synthesis of 2-(1-aryl-1H-tetrazol-5-yl)-thieno[2,3-b]pyridine derivatives
  作者：Nikolai Yu. Koltsov

  DOI：10.1007/s10593-019-02533-2

  日期：2019.8

  Alkylation of 4,6-dimethyl-2-sulfanylpyridine-3-carbonitrile with 1-aryl-5-(chloromethyl)-1H-tetrazoles yielded 2-[(1-aryl-1H-tetrazol-5-yl)methyl]sulfanyl}-4,6-dimethylpyridine-3-carbonitriles, which easily cyclize by the action of bases to form 2-(1H-tetrazol-5-yl)-thieno[2,3-b]pyridine derivatives. The use of excess base in the alkylation step leads to direct formation of cyclized products in high yields

  用1-芳基-5-（氯甲基）-1 H-四唑烷基化4，6-二甲基-2-磺酰基吡啶-3-甲腈，得到2-[（（1-芳基-1 H-四唑-5-基）甲基] ]硫烷基} -4,6-二甲基吡啶-3-腈，其在碱的作用下容易环化形成2-（1 H-四唑-5-基）-噻吩并[2,3- b ]吡啶衍生物。在烷基化步骤中使用过量的碱导致以高收率直接形成环化产物。