3-甲基-2-联苯胺 | 14294-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲基-2-联苯胺
• 中文别名: 3-甲基联苯-2-胺
• 英文名称: 3-methyl-[1,1'-biphenyl]-2-amine
• 英文别名: 2-amino-3-methylbiphenyl；2-methyl-6-phenylaniline
• CAS: 14294-33-8
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: NTRUIXLRNRHYNS-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  309.3±11.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-甲基-2-联苯胺 在 PPA 作用下， 以 吡啶 为溶剂， 生成 6-(3-Chlorophenyl)-4-methylphenanthridine
  参考文献：
  名称：

  Potential antitumor agents. 55. 6-Phenylphenanthridine-4-carboxamides: a new class of DNA-intercalating antitumor agents

  摘要：

  Derivatives of the DNA-intercalating agent N-[2-(dimethylamino)ethyl]phenanthridine-4-carboxamide have been prepared and shown to have moderate in vivo antitumor activity against both the P388 leukemia and Lewis lung carcinoma. This demonstrates that the effective pharmacophore in the broad class of tricyclic carboxamides is not limited to linear tricyclic chromophores. Both 7 and the 6-phenyl derivative 10 have identical DNA binding properties, suggesting that the phenyl ring of 10 is not involved in the DNA intercalation site. A series of phenyl-substituted derivatives of 10 was evaluated. Aza substituents led to compounds with the highest in vivo cytotoxicity and in vivo P388 activity, but the in vivo solid tumor activity of the substituted 6-phenylphenanthridine-4-carboxamides was in general low.

  DOI：

  10.1021/jm00399a015
• 作为产物：
  描述：

  2-甲基-N-甲酰苯胺 在 盐酸 、 silver tetrafluoroborate 、 palladium diacetate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 3-甲基-2-联苯胺
  参考文献：
  名称：

  Palladium-Catalyzed C(sp²)–H Arylation Using Formamide as a Transformable Directing Group

  摘要：

  A new process for the ortho arylation of formanilides through palladium-catalyzed C-H activation is described. Formamide is reported as a transformable directing group in the transition-metal-catalyzed C-H functionalization reaction. The resulting biarylformanilide products can be readily transformed to the corresponding biarylisocyanides or N-heterocycles.

  DOI：

  10.1021/jo5007043
• 作为试剂：
  描述：

  tetrafluoroboric acid 、 potassium selenocyanate 、 sodium nitrite 在 3-甲基-2-联苯胺 作用下， 以 水 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  通过可见光介导的自由基环化合成硒杂环

  摘要：

  开发了一种从芳基重氮盐开始合成硒杂环的方法。一锅法和随后的可见光介导的银催化环化能够在没有光催化剂的情况下合成硒杂环。反应在温和条件下进行，没有使用有毒或敏感的试剂。

  DOI：

  10.1002/adsc.202100969

文献信息

• Biphenyl-substituted guanidine derivatives useful as hypoglycaemic agents
  申请人：The Boots Company

  公开号：US05302720A1

  公开（公告）日：1994-04-12

  Compounds of formula I ##STR1## and their salts in which R.sub.1 is optionally substituted phenyl, R.sub.2 is alkyl, cycloalkyl or optionally substituted amino, or R.sub.2 and R.sub.3 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted heterocyclic ring or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form an optionally substituted heterocyclic ring and R.sub.5 is H, halo, alkyl, alkoxy, trifluoromethyl or a group of formula S(O).sub.m R.sub.8 in which m is 0, 1 or 2 and R.sub.8 is alkyl have utility in the treatment of diabetes particularly in the treatment of hyperglycaemia.

  化合物的化学式I ##STR1## 及其盐，其中R.sub.1 可选择地是取代苯基，R.sub.2 是烷基、环烷基或可选择地取代的氨基，或者R.sub.2 和R.sub.3 与它们连接的氮和碳原子一起形成可选择地取代的杂环环或者R.sub.3 和R.sub.4 与它们连接的氮原子一起形成可选择地取代的杂环环，R.sub.5 是H、卤素、烷基、烷氧基、三氟甲基或者化学式S(O).sub.m R.sub.8 的基团，其中m 为0、1 或2，R.sub.8 是烷基，在糖尿病治疗中特别在高血糖治疗中具有用途。
• [EN] SULFONAMIDES AS INHIBITORS OF BCL-2 FAMILY PROTEINS FOR THE TREATMENT OF CANCER<br/>[FR] SULFAMIDES UTILISÉS COMME INHIBITEURS DES PROTÉINES DE LA FAMILLE DE BCL-2 DANS LE TRAITEMENT DU CANCER
  申请人：NOVARTIS AG

  公开号：WO2011029842A1

  公开（公告）日：2011-03-17

  The present invention includes novel compound and methods of treating a disease or disorder by antagonizing Bcl-2 family proteins, particularly compounds of Formula (I) or pharmaceutically acceptable salt thereof, as well as methods of treating a disease, disorder, or syndrome associated with Bcl-2 inhibition, particularly hyperproliferative diseases. The present invention also includes pharmaceutical compositions including compounds of formula (I) and pharmaceutically acceptable salts thereof.

  本发明涉及一种新型化合物和通过拮抗Bcl-2家族蛋白治疗疾病或紊乱的方法，特别是公式(I)的化合物或其药用盐，以及治疗与Bcl-2抑制相关的疾病、紊乱或综合征的方法，特别是高增殖性疾病。本发明还包括包括公式(I)的化合物和其药用盐的药物组合物。
• Electrochemical initiation of electron-catalyzed phenanthridine synthesis by trifluoromethylation of isonitriles
  作者：M. Lübbesmeyer、D. Leifert、H. Schäfer、A. Studer

  DOI：10.1039/c7cc09302k

  日期：——

  The electron-catalyzed formation of phenanthridines starting from isonitriles initiated by an electrochemical reduction of the Togni reagent is presented. The required number of faradays per mole of starting material and the respective yields clearly show the catalytic character of the electron in this reaction. The mechanism is supported by cyclic voltammetry experiments.

  提出了由Togni试剂的电化学还原引发的由异腈开始的菲啶的电子催化形成。每摩尔起始原料所需的法拉第数和相应的产率清楚地表明了该反应中电子的催化特性。该机理得到循环伏安法实验的支持。
• Free-Amine-Directed Alkenylation of C(sp²)H and Cycloamination by Palladium Catalysis
  作者：Zunjun Liang、Long Ju、Yongju Xie、Lehao Huang、Yuhong Zhang

  DOI：10.1002/chem.201202672

  日期：2012.12.3

  A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and cycloamination is described. Substituted biaryl‐2‐amines react with various alkenes, including electron‐deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds

  描述了一种新的协议，用于钯催化的C（sp 2）H键和环氨基化的游离胺定向的烯基化。取代的联芳基-2-胺可与各种烯烃反应，包括缺电子的烯烃，芳基烯烃和烷基烯烃，从而产生具有区域选择性的相应菲啶。使用α支链的苯乙烯会导致形成具有七元胺环的三环化合物。该方法通过游离胺定向的烯基化和随后的加氢胺化环化反应进行。
• Co(acac)₂/O₂-Mediated Oxidative Isocyanide Insertion with 2-Aryl Anilines: Efficient Synthesis of 6-Amino Phenanthridine Derivatives
  作者：Tong-Hao Zhu、Shun-Yi Wang、Yang-Qing Tao、Tian-Qi Wei、Shun-Jun Ji

  DOI：10.1021/ol500286x

  日期：2014.2.21

  protocol for the creation of 6-amino phenanthridine derivatives by Co(acac)2-catalyzed isocyanide insertion with 2-aryl anilines under an O2 atmosphere via homolytic aromatic substitution (HAS) type C–H functionalization has been developed. This reaction not only proceeds smoothly utilizing O2 as the oxidant but also provides a new approach to construct phenanthridine derivatives utilizing readily available

  通过在O 2气氛下通过均相芳香族取代（HAS）C–H型官能化作用，通过Co（acac）2催化的异氰酸酯与2-芳基苯胺的插入来创建6-氨基菲啶衍生物的新颖有效的协议已被开发出来。该反应不仅利用O 2作为氧化剂顺利进行，而且提供了一种利用容易获得的2-芳基苯胺与异氰酸酯代替具有不同自由基前体的2-异氰基联芳基来构建菲啶衍生物的新方法。