4-(3-甲基苯氧基)苯-1,2-二胺 | 43156-15-6

• 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: 4-(3-甲基苯氧基)苯-1,2-二胺
• 英文名称: 4-m-Tolyloxy-benzene-1,2-diamine
• 英文别名: 1,2-Benzenediamine, 4-(3-methylphenoxy)-；4-(3-methylphenoxy)benzene-1,2-diamine
• CAS: 43156-15-6
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: YRPXGOAXCUIMLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.4±32.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-甲基苯氧基)苯-1,2-二胺 在 sodium hydride 作用下， 以 邻二甲苯 为溶剂， 反应 13.0h， 生成 7-(m-methylphenoxy)-4-(p-methylphenyl)-2-methylthio-3H-[1,5]benzodiazepine
  参考文献：
  名称：

  2-甲硫基-3 H -7-[（o- ; m-和对-取代的）苯氧基] -4-（对-取代的苯基）-[1,5]苯并二氮杂的合成及光谱性质

  摘要：

  一系列十一种新的2-甲硫基-3 H -7-[（o- ; m-和对-取代的）苯氧基] -4-（对-取代的苯基）-[1,5]苯并二氮杂通过缩合4-[（o- ; m-和p -R 1）苯氧基] -1,2-苯基苯二胺与3,3-二巯基-1-（p -R 2-苯基）-合成药理活性2-prop-1-1。然后，将得到的1 H- [1，5]苯并二氮杂-2-硫酮用氢化钠和甲基碘处理。ir，1 H nmr，13证实了所有产品的结构C nmr和ms。

  DOI：

  10.1002/jhet.5570390633
• 作为产物：
  描述：

  间甲酚 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-(3-甲基苯氧基)苯-1,2-二胺
  参考文献：
  名称：

  New benzimidazole-2-urea derivates as tubulin inhibitors

  摘要：

  Emerging drug resistance and other drawbacks limit tubulin inhibitors' therapeutic applications and developing novel tubulin inhibitors still attracts intensive efforts. We describe the discovery and structure-activity relationship study of a series of benzimidazole-2-urea derivatives as novel β tubulin inhibitors. The representative compound 6o potently suppressed the proliferation of a panel of human cancer cells (NCI-H460, Colo205, K562, A431, HepG2, Hela, MDA-MB-435S) with IC50 values of 0.040, 0.050, 0.006, 0.026, 1.774, 0.452 and 0.052 μM, respectively. Compound 6o obviously inhibited NCI-H460 spindles formation and induced cell cycle arrest at G2/M phase at 0.10 μM. Computational study suggested that 6o interacts with β tubulin in a novel binding mode. Our results suggested that benzimidazole-2-urea derivatives might be promising tubulin inhibitors with novel binding mode for further development.

  DOI：

  10.1016/j.bmcl.2014.07.035

文献信息

• Synthesis and spectral properties of methyl 5-[(<i>o</i>-,<i>m</i>-, and<i>p</i>-R)-phenoxy]-2-benzimidazolecarbamate
  作者：Eduardo Cortés Cortés、Luis Angel Araluce Anaya

  DOI：10.1002/jhet.5570340307

  日期：1997.5

  The preparation of eleven novel methyl 5-[(o-, m-, p-R)-phenoxy-2-benzimidazolecarbamates with possible pharmacological activity as anthelmintics is described. The structure of all products was corroborated by ir, 1H-nmr, 13C-nmr and mass spectra.

  描述了十一种新颖的5-[（o-，m-，p -R）-苯氧基-2-苯并咪唑氨基甲酸酯甲酯，其具有可能的药理活性作为驱虫药。ir，1 H-nmr，13 C-nmr和质谱证实了所有产物的结构。
• Synthesis and spectral properties of 2,3-dihydro-4-(<i>para</i>-substituted-phenyl)-7-[(<i>o</i>-,<i>m</i>-, and<i>p</i>-substituted)phenoxy]-1<i>H</i>-1,5-benzodi-azepine-2-thiones
  作者：Eduardo CortÉS Cortés、Carlos M. Alcocer Castrejón

  DOI：10.1002/jhet.5570340628

  日期：1997.11

  A series of twelve new 2,3-dihydro-4-(para-substituted-phenyl)-7-[(o-, m-, and p-substituted)phenoxy]-1H-1,5-benzodiazepine-2-thiones, which have potentially useful pharmacological properties, has been synthesized by condensing the 3,3-dimercapto-1-(para-substituted phenyl)-2-propen-1-one with 3,4-diaminophenyl-R-phenyl ethers. The structure of all products was corroborated by ir, 1H-nmr, 13C-nmr and

  一系列十二个新的2,3-二氢-4-（对取代的苯基）-7-[（邻，间和对取代的）苯氧基] -1 H -1,5-苯并二氮杂-2-硫酮，它具有潜在的有用的药理性质，已经通过缩合3,3-二巯基-1-（合成对-取代的苯基）-2-丙烯-1-酮与3,4- diaminophenyl- - [R -苯基醚。ir，1 H-nmr，13 C-nmr和ms证实了所有产物的结构。
• Synthesis and spectral properties of 2,3-dihydro-4-(<i>paramethylphenyl</i>)-7-[(<i>o, m-</i>, and<i>p</i>-substituted)phenoxy]-1<i>H</i>-1,5-benzodiazepine-2-thiones
  作者：Eduardo Corés Cortés、Mario Martínez Torres

  DOI：10.1002/jhet.5570340337

  日期：1997.5

  A series of twelve new 2,3-dihydro-4-(para-methylphenyl)-7-[(o-, m-, and p-substituted)phenoxy]-1H-1,5-benzodiazepine-2-thiones. which have potentially useful pharmacological properties, has been synthesized by condensing the 3,3-dimercapto-1-(p-methylphenyl)-2-propen-1-one with 3,4-diaminophenyl-R-phenyl ethers. The structure of all products was corroborated by ir; 1H-nmr; 13C-nmr and ms.

  一系列十二个新的2,3-二氢-4-（对甲基苯基）-7-[（邻，间和对取代的）苯氧基] -1 H -1,5-苯并二氮杂-2-硫酮。通过将3，3-二巯基-1-（对甲基苯基）-2-丙烯-1-酮与3，4-二氨基苯基-R-苯基醚缩合，合成了具有潜在有用药理性质的化合物。ir证实了所有产品的结构；1 H-核磁共振; 13 C-nmr和ms。
• Optical members made of polymide resins
  申请人：——

  公开号：US20030064235A1

  公开（公告）日：2003-04-03

  For providing a polyimide optical component exhibiting good physical properties inherent to a polyimide, i.e., heat resistance, mechanical properties, electric properties, thermal oxidation stability and chemical resistance, as well as good transparency and a high refractive index, this invention, this invention essentially uses a particular diamine and a particular tetracarboxylic dianhydride to give an optical component made of a polyimide having a motif represented by general formula (1): 1 wherein in general formula (1), A represents general formula (2), (3) or (4); X represents a direct bond, —O—, —SO 2 — or —C(CF 3 ) 2 —; in general formula (2), R 1 and R 2 represent H, Cl, Br, CH 3 or CF 3 ; in general formula (3), A 1 represents —O—, —S—, —CO—, —CH 2 —, —SO 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 —; in general formula (4), A 2 represents a direct bond, —O—, —S—, —CO—, —SO 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 —.

  为了提供一种聚酰亚胺光学元件，使其具有聚酰亚胺固有的良好物理性能，即耐热性、机械性能、电性能、热氧化稳定性和耐化学性，以及良好的透明度和高折射率，本发明主要使用一种特定的二胺和一种特定的四羧酸二酐，以得到一种由具有通式(1)表示的图案的聚酰亚胺制成的光学元件： 1 其中，在通式（1）中，A 代表通式（2）、（3）或（4）；X 代表直接键、-O-、-SO 2 - 或 -C(CF 3 ) 2 -; 在通式(2)中，R 1 和 R 2 代表 H、Cl、Br、CH 3 或 CF 3 ; 在通式（3）中，A 1 代表-O-、-S-、-CO-、-CH 2 -、-SO 2 -、-C（CH 3 ) 2 - 或 -C(CF 3 ) 2 -; 在通式(4)中，A 2 代表直接键、-O-、-S-、-CO-、-SO 2 -、-C（CH 3 ) 2 - 或 -C(CF 3 ) 2 -.
• New benzimidazole-2-urea derivates as tubulin inhibitors
  作者：Wenna Wang、Dexin Kong、Huimin Cheng、Li Tan、Zhang Zhang、Xiaoxi Zhuang、Huoyou Long、Yang Zhou、Yong Xu、Xiaohong Yang、Ke Ding

  DOI：10.1016/j.bmcl.2014.07.035

  日期：2014.9

  Emerging drug resistance and other drawbacks limit tubulin inhibitors' therapeutic applications and developing novel tubulin inhibitors still attracts intensive efforts. We describe the discovery and structure-activity relationship study of a series of benzimidazole-2-urea derivatives as novel β tubulin inhibitors. The representative compound 6o potently suppressed the proliferation of a panel of human cancer cells (NCI-H460, Colo205, K562, A431, HepG2, Hela, MDA-MB-435S) with IC50 values of 0.040, 0.050, 0.006, 0.026, 1.774, 0.452 and 0.052 μM, respectively. Compound 6o obviously inhibited NCI-H460 spindles formation and induced cell cycle arrest at G2/M phase at 0.10 μM. Computational study suggested that 6o interacts with β tubulin in a novel binding mode. Our results suggested that benzimidazole-2-urea derivatives might be promising tubulin inhibitors with novel binding mode for further development.