4-[(2-Bromoanilino)methyl]-2-methoxyphenol | 1019575-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(2-Bromoanilino)methyl]-2-methoxyphenol
• CAS: 1019575-54-2
• 化学式: C₁₄H₁₄BrNO₂
• mdl: MFCD11144789
• 分子量: 308.175
• InChiKey: ZQECYWPAXUERSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2-Bromoanilino)methyl]-2-methoxyphenol 在 caesium carbonate 、 4-(benzo[b]thiophen-3-yl)-2,6-di-tert-butylphenol 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 benzyl-3-methoxy-4-oxospiro[cyclohexane-1,3'-indoline]-2,5-diene-1'-carboxylate
  参考文献：
  名称：

  可见光诱导的酚类氧化还原中性分子内脱芳螺环化

  摘要：

  本文描述的是由可见光诱导的氧化还原中性分子内脱芳环化。光化学环化由酚盐阴离子衍生的光催化剂催化，并产生螺环己二烯酮。机理实验表明，芳基卤化物在可见光照射下通过单电子转移 (SET) 过程还原为芳基自由基。芳基与酚盐阴离子部分的亲电加成产生自由基阴离子中间体，通过第二个 SET 过程回收光催化剂。

  DOI：

  10.1021/acs.orglett.3c01257
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-[(2-Bromoanilino)methyl]-2-methoxyphenol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel N, N′-disubstituted urea and thiourea derivatives as potential anti-melanoma agents

  摘要：

  Two series of urea and thiourea derivatives (1a-11a, 1b-11b) have been synthesized; all the 22 compounds were reported for the first time. Their anti-proliferative activities against the melanoma cell line B16-F10 were evaluated. Among the compounds tested, compound 6b exhibited the most potent activity in melanoma cells growth inhibition (IC50 = 0.33 mu M). The bioassay tests showed that anti-proliferative activities of these novel compounds were possibly caused by inhibition of ERK1/2 phosphorylation level. Therefore, compound 6b can be a potential anti-melanoma agent and an inhibitor of ERK1/2 phosphorylation deserving further research.

  DOI：

  10.3109/14756366.2011.608665

文献信息

• Synthesis and biological evaluation of novel N, N′-disubstituted urea and thiourea derivatives as potential anti-melanoma agents
  作者：Qing-Shan Li、Peng-Cheng Lv、Huan-Qiu Li、Xiang Lu、Zi-Lin Li、Ban-Feng Ruan、Hai-Liang Zhu

  DOI：10.3109/14756366.2011.608665

  日期：2012.10.1

  Two series of urea and thiourea derivatives (1a-11a, 1b-11b) have been synthesized; all the 22 compounds were reported for the first time. Their anti-proliferative activities against the melanoma cell line B16-F10 were evaluated. Among the compounds tested, compound 6b exhibited the most potent activity in melanoma cells growth inhibition (IC50 = 0.33 mu M). The bioassay tests showed that anti-proliferative activities of these novel compounds were possibly caused by inhibition of ERK1/2 phosphorylation level. Therefore, compound 6b can be a potential anti-melanoma agent and an inhibitor of ERK1/2 phosphorylation deserving further research.
• Redox-Neutral Intramolecular Dearomative Spirocyclization of Phenols Induced by Visible Light
  作者：Linlin Zhang、Fengchi Hu、Lei Shen、Lijuan Gao、Yunhong Yang、Zhiqiang Pan、Chengfeng Xia

  DOI：10.1021/acs.orglett.3c01257

  日期：2023.5.5

  spirocyclohexadienone. Mechanistic experiments revealed that the aryl halide was reduced to aryl radical via the single-electron transfer (SET) process under visible light irradiation. The electrophilic addition of an aryl radical with the phenolate anion moiety gave a radical anion intermediate, which recycled the photocatalyst by a second SET process.

  本文描述的是由可见光诱导的氧化还原中性分子内脱芳环化。光化学环化由酚盐阴离子衍生的光催化剂催化，并产生螺环己二烯酮。机理实验表明，芳基卤化物在可见光照射下通过单电子转移 (SET) 过程还原为芳基自由基。芳基与酚盐阴离子部分的亲电加成产生自由基阴离子中间体，通过第二个 SET 过程回收光催化剂。