5-methyl-2-phenyl-2H-tetrazole | 22706-20-3

• 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-methyl-2-phenyl-2H-tetrazole
• 英文别名: 2-Phenyl-5-methyl-tetrazol；2-Phenyl-5-methyl-tetrazole；5-methyl-2-phenyltetrazole
• CAS: 22706-20-3
• 化学式: C₈H₈N₄
• 分子量: 160.178
• InChiKey: DWFDADZCRATSDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-methyl-2-phenyl-2H-tetrazole 在 四氯苯醌 、 对苯二酚 作用下， 以 乙腈 、 xylene 为溶剂， 反应 9.0h， 生成 5-甲基-2-苯基吡唑-3-甲酸甲酯
  参考文献：
  名称：

  Fliege, Werner; Huisgen, Rolf; Clovis, James S., Chemische Berichte, 1983, vol. 116, # 9, p. 3039 - 3061

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 在 tetrafluoroboric acid 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 5-methyl-2-phenyl-2H-tetrazole
  参考文献：
  名称：

  One-Pot Reactions for Synthesis of 2,5-Substituted Tetrazoles from Aryldiazonium Salts and Amidines

  摘要：

  One-pot sequential reactions of aryldiazonium salts with amidines followed by the treatment of I-2/KI under basic conditions provide 2,5-disubstituted tetrazoles in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, and high yields, making this methodology practical.

  DOI：

  10.1021/acs.orglett.5b03068

文献信息

• Chan–Evans–Lam Couplings with Copper Iminoarylsulfonate Complexes: Scope and Mechanism
  作者：Valérie Hardouin Duparc、Guillaume L. Bano、Frank Schaper

  DOI：10.1021/acscatal.8b01881

  日期：2018.8.3

  Copper(II) pyridyliminoarylsulfonate complexes with chloride or triflate counteranions were employed in Chan–Evans–Lam (CEL) couplings of N-nucleophiles and arylboronic acids. The complexes avoided typical side reactions in CEL couplings, and an excess of boronic acid was not required. Water was tolerated, and addition of neither base nor other additives was necessary. Primary amines, acyclic and cyclic

  N-亲核试剂和芳基硼酸的Chan-Evans-Lam（CEL）偶联反应中使用了吡啶（氯）吡啶基亚氨基磺酸磺酸铜与三氟甲磺酸酯或三氟甲磺酸酯抗衡离子的配合物。该络合物避免了CEL偶联中的典型副反应，并且不需要过量的硼酸。可以耐受水，并且不需要添加碱或其他添加剂。伯胺，无环和环状仲胺，苯胺，氨基苯酚，咪唑，吡唑和苯基四唑可以在25或50°C下用2.5 mol％的催化剂定量芳基化。详细研究了反应动力学。动力学和光谱学研究为形成非生产性的铜-底物复合物提供了证据。苯胺-苯硼酸加合物的形成是反应速率对苯硼酸浓度的零级依赖性的原因。动力学证据表明，反应步骤的顺序是金属转移，亲核配位和氧化。由于催化循环中较慢的Cu（II）/ Cu（III）氧化，偶联剂与缺电子的芳基硼酸的偶联性能较差。光氧化还原催化部分解决了这个问题，但事实证明添加乙酸铜作为外部氧化剂更为有效。
• [Cu(OH)(TMEDA)]₂Cl₂-Catalyzed Regioselective 2-Arylation of 5-Substituted Tetrazoles with Boronic Acids under Mild Conditions
  作者：Takuya Onaka、Hideaki Umemoto、Yasuyoshi Miki、Akira Nakamura、Tomohiro Maegawa

  DOI：10.1021/jo500862t

  日期：2014.7.18

  A mild and regioselective 2-arylation of 5-substituted tetrazoles is described. The reaction proceeds regioselectively with a variety of arylboronic acids in the presence of [Cu(OH)(TMEDA)]2Cl2 to afford 2,5-disubstituted tetrazoles. This is the first report of highly regioselective arylation of 5-alkyltetrazoles.

  描述了5-取代的四唑的温和和区域选择性的2-芳基化。在[Cu（OH）（TMEDA）] 2 Cl 2的存在下，反应与多种芳基硼酸进行区域选择性反应，得到2,5-二取代的四唑。这是5-烷基四唑类的高度区域选择性芳基化的首次报道。
• [EN] NONPEPTIDE INHIBITORS OF MATRIX METALLOPROTEINASES<br/>[FR] INHIBITEURS NON PEPTIDIQUES DE METALLOPROTEINASES MATRICIELLES
  申请人：SOUTHERN RES INST

  公开号：WO2005092844A1

  公开（公告）日：2005-10-06

  Disclosed are selective inhibitors of matrix metalloproteinases represented by the following formula (I). wherein X is (CH2)nO, (CH2)nS, (CH2)nNR1, (CH2)n(CH2), or CH=CH, wherein n = 0, 1, or 2; R and R1 are, independently, a substituted or unsubstitued alkyl, alkenyl, alkynyl, aryl, heteroaryl group, cycloalkyl, heterocycloalkyl, cycloalkenyl, or heterocycloalkenyl; and Z is NH or CH2; or a pharmaceutically acceptable salt thereof. Also disclosed are methods of making such compounds and methods of using such compounds to inhibit tumor progression and to treat diseases such as arthritis.

  本发明涉及选择性基质金属蛋白酶抑制剂，其由以下式（I）表示。其中，X为（CH2）nO，（CH2）nS，（CH2）nNR1，（CH2）n（CH2）或CH=CH，其中n = 0、1或2；R和R1独立地为取代或未取代的烷基、烯基、炔基、芳基、杂芳基、环烷基、杂环烷基、环烯基或杂环烯基；Z为NH或CH2；或其药学上可接受的盐。本发明还涉及制备这种化合物的方法以及使用这种化合物抑制肿瘤进展和治疗关节炎等疾病的方法。
• Benzimidazole derivatives and their use as protein kinases inhibitors
  申请人：Berdini Valerio

  公开号：US20070135477A1

  公开（公告）日：2007-06-14

  The invention provides compounds of the formula (1): The compounds have activity against cyclin depdenent kinases, glycogen synthase kinase and Auroa kinases and are therefore useful to treat cancer and viral diseases.

  该发明提供了式（1）的化合物： 这些化合物具有对环素依赖性激酶、糖原合成酶激酶和Auroa激酶的活性，因此可用于治疗癌症和病毒性疾病。
• Thiazole And Isothiazole Derivatives That Modulate The Activity Of CDK, GSK And Aurora Kinases
  申请人：Berdini Valerio

  公开号：US20080312223A1

  公开（公告）日：2008-12-18

  The invention provides a compound of the formula (I): or a salt, N-oxide, tautomer or solvate thereof, wherein X is CR 5 or N; each of Q 1 and Q 2 is a carbon atom; Q 3 is selected from S and CH; Q 4 is selected from CR 2 and S; provided that one of Q 3 and Q 4 is S and the other of Q 3 and Q 4 is not S; wherein when Q 3 is S, there is a double bond between Q 1 and Q 4 and a double bond between Q 2 and the adjacent ring nitrogen atom N; and when Q 4 is S, there is a double bond between Q 1 and Q 2 , and a double bond between Q 3 and the adjacent ring nitrogen atom N; A is a bond or —(CH 2 ) m —(B) n —; B is C═O, NR 8 (C═O) or O(C═O) wherein R 1 is hydrogen or C1_4 hydrocarbyl optionally substituted by hydroxy or C 1-4 alkoxy; m is 0, 1 or 2; n is 0 or 1; R o is hydrogen or, together with NR g when present, forms a group —(CH 2 ) p — wherein p is 2 to 4; R 1 is hydrogen, a carbocyclic or heterocyclic group having from 3 to 12 ring members, or an optionally substituted C 1-8 hydrocarbyl group; R 2 is hydrogen, halogen, methoxy, or a C 1-4 hydrocarbyl group optionally substituted by halogen, hydroxyl or methoxy; R 3 and R 4 together with the carbon atoms to which they are attached form an optionally substituted fused carbocyclic or heterocyclic ring having from 5 to 7 ring members of which up to 3 can be heteroatoms selected from N, O and S; and R 5 is hydrogen, a group R 2 or a group R 10 wherein R 10 is as defined in the claims. The compounds have activity as inhibitors of cyclin dependent kinases, glycogen synthase kinases and Aurora kinases.

  本发明提供一种化合物，其化学式为（I）或其盐，N-氧化物，互变异构体或溶剂化物，其中X为CR5或N; Q1和Q2中的每一个都是碳原子; Q3从S和CH中选择; Q4从CR2和S中选择; 假设Q3和Q4中的一个是S，而另一个不是S; 当Q3为S时，Q1和Q4之间有一个双键，Q2和相邻的环氮原子N之间有一个双键; 当Q4为S时，Q1和Q2之间有一个双键，并且Q3和相邻的环氮原子N之间有一个双键; A是键或-(CH2)m-(B)n-; B为C═O，NR8（C═O）或O（C═O），其中R1为氢或C1_4烃基，可选择地被羟基或C1-4烷氧基取代; m为0、1或2; n为0或1; Ro为氢或与NRg一起形成一个群体-(CH2)p-，其中p为2至4; R1为氢，具有3至12个环成员的碳环或杂环基，或可选择地被取代的C1-8烃基基团; R2为氢、卤素、甲氧基或可选择地被卤素、羟基或甲氧基取代的C1-4烃基基团; R3和R4与它们所连接的碳原子一起形成一个可选择地取代的融合碳环或杂环环，其具有5至7个环成员，其中最多可有3个异原子，选择自N、O和S; R5为氢、R2基团或R10基团，其中R10如权利要求所定义。该化合物具有作为细胞周期依赖性激酶、糖原合成酶激酶和极化子激酶的抑制剂的活性。