4-bromo-2-((p-tolylamino)methyl)phenol

• 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-bromo-2-((p-tolylamino)methyl)phenol
• 英文别名: 4-Bromo-2-[(4-methylanilino)methyl]phenol
• 化学式: C₁₄H₁₄BrNO
• 分子量: 292.175
• InChiKey: BEBHKMBSPJHZCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-2-((p-tolylamino)methyl)phenol 在 碘苯二乙酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 0.66h， 生成 2-bromo-7,10-dimethyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine
  参考文献：
  名称：

  邻氨基-C（sp 2）–H官能化合成叔胺的无金属二芳基二胺，合成二苯并x氮平和-ones

  摘要：

  利用苯乙酸碘（III）介导的叔胺与适当取代的邻羟基苄基和苯基基团的蛋白反应，可促进邻-C（sp 2）-H官能化，从而提供二芳基醚。原位产生的所得二芳基醚中邻-CHO和仲胺官能团的存在被用于合成二苯并x氮杂和二苯并a氮杂酮。温和的条件和相对较宽的底物范围以及二芳基醚进一步多样化的潜力是该方法的重点。

  DOI：

  10.1021/acs.orglett.7b03328
• 作为产物：
  描述：

  (E)-4-bromo-2-((p-tolylimino)methyl)phenol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 4-bromo-2-((p-tolylamino)methyl)phenol
  参考文献：
  名称：

  Synthesis and Biological Activity of Some 3-Aryl-3,4-dihydro-2H-benz[e]- 1,3-oxazines/6-bromo-3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines

  摘要：

  N-(2-羟基)-苄基芳胺(1)在甲醇中与甲醛进行环化反应，在65-68°C下0.5-1.0小时内，可以高产率地得到几乎纯的3-芳基-3,4-二氢-2H-苯并[e]-1,3-恶嗪/6-溴-3-芳基-3,4-二氢-2H-苯并[e]-1,1-恶嗪(2)。这些化合物随后被用于针对革兰氏阳性细菌（金黄色葡萄球菌，MTCC 96）和革兰氏阴性细菌（大肠杆菌，MTCC 739）的抗菌活性研究。为了评估抗真菌活性，使用的真菌为白色念珠菌。所有化合物的最低抑制浓度是通过微量肉汤稀释法确定的。

  DOI：

  10.14233/ajchem.2013.14091

文献信息

• A Quick Route for the Synthesis of 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazin-2-ones
  作者：Davender Kumar Shukla、Manju Rani、Arif Ali Khan

  DOI：10.14233/ajchem.2013.14053

  日期：——

  N-(2-Hydroxy)-benzyl-arylamines (1) gave substantially pure 3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazin-2-one 2 on cyclization with carbonyldiimidazole in DMSO in 20-30 min at 20-25 ºC in excellent yields.

  N-(2-羟基)-苄基-芳香胺（1）在20-25 ºC的DMSO中与碳酰二咪唑环化，20-30分钟后获得了3-芳基-3,4-二氢-2H-benz[e]-1,3-噁唑啉-2-酮（2），产率非常高。
• Synthesis of New Benzoxazaphosphinine/Benzoxazaphosphole/Diazaphosphaphenalene‐2‐sulfides using Lawesson's Reagent
  作者：G. Syam Prasad、B. Hari Babu、C. Devendranath Reddy、C. Naga Raju、C. Suresh Reddy

  DOI：10.1080/00397910701649148

  日期：2007.12.1

  Abstract Synthesis of new benzoxazaphosphinine/benzoxazaphosphole/diazaphosphaphenalene 2‐sulfides were accomplished by the reaction of Lawesson's reagent (LR) with 4‐bromo‐2‐[(phenylamino) methyl]phenol (1a), 4‐bromo‐2‐[(4‐chloro/bromo/methoxy/methylphenyl‐amino)methyl]phenol (1b–e), 4‐bromo‐2‐[(benzylamino)methyl]phenol (1f), 2‐amino‐4‐chlorophenol (2a)/2‐amino‐4‐methylphenol (2b), 1,8‐diaminonaphthalene

  摘要 通过劳森试剂 (LR) 与 4-溴-2-[(苯氨基) 甲基]苯酚 (1a)、4-溴-2-[(4 -氯/溴/甲氧基/甲基苯基-氨基）甲基]苯酚（1b-e），4-溴-2-[（苄基氨基）甲基]苯酚（1f），2-氨基-4-氯苯酚（2a）/2-氨基-4-甲基苯酚 (2b​​), 1,8-二氨基萘 (3) 分别在无水甲苯中。产物 4a-f、5a-b 和 6 通过 IR、1H、13C、31P NMR 和质谱进行表征。
• Synthesis, Characterization, Stability and Cytotoxic Evaluation of Novel Titanium(IV) Complexes of 8-Hydroxyquinoline and 2-Hydroxy-N-phenylbenzylamine Derivatives
  作者：Blassan Samuel、Madhvesh Pathak

  DOI：10.14233/ajchem.2020.22505

  日期：2020.2.10

  A new class of moisture stable heteroleptic titanium(IV) complexes, synthesized from 8-hydroxyquinoline of the type [(Q)2Ti(2-O-5-X-C6H3CH2NC6H4R] (3a-j), was prepared by reacting the antecedent molecule [(Q2)Ti(OiPr)2] (2) with various 2-hydroxy-N-phenyl-benzylamine analogues in 1:1 molar ratios in dry toluene (where, HQ = 8-hydroxyquinoline; iPr = isopropyl; R = H, 4-CH3, 4-OCH3, 2-Cl, 4-Cl, 2-Br, 4-Br; X= H, Br). Moisture sensitive study disclosed that these new metal complexes were unreacted for 72 h. Mass spectral data were employed for proving the mono-nuclearity of the new derivatives. Thermal decomposition pattern of the new derivatives was explained by thermogravimetric analyses. Elemental analyses data are in concordance with their expected values. The hexa-coordinated way of titanium-ligand linkage is further proved through NMR, FTIR, and UV-visible spectral studies. The cytotoxic efficiency of new complexes was tested against MDA-MB-231 human breast carcinoma cell line. Complex 3a exhibited the highest cytotoxic potential of 0.039 μM in comparison to all its analogues of this series by employing cisplatin as the standard

  一种新型的具有湿度稳定性的杂环钛（IV）配合物类别，由8-羟基喹啉[(Q)2Ti（2-O-5-X-C6H3CH2NC6H4R]（3a-j）合成，通过在干燥甲苯中以1:1摩尔比反应前体分子[(Q2)Ti（OiPr）2]（2）与各种2-羟基-N-苯基苄胺类似物（其中，HQ = 8-羟基喹啉; iPr = 异丙基; R = H，4-CH3，4-OCH3，2-Cl，4-Cl，2-Br，4-Br; X = H，Br）。湿度敏感性研究表明，这些新金属配合物在72小时内未反应。质谱数据用于证明新衍生物的单核性。通过热重分析解释了新衍生物的热分解模式。元素分析数据与预期值一致。通过NMR，FTIR和UV-Visible光谱研究进一步证明了钛-配体键合的六配位方式。测试了新配合物对MDA-MB-231人乳腺癌细胞系的细胞毒性效率。与所有同系列的类似物相比，3a复合物表现出最高的细胞毒性潜力（0.039μM），以顺铂为标准。
• Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors
  作者：Zi-Lin Li、Qing-Shan Li、Hong-Jia Zhang、Yang Hu、Di-Di Zhu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.06.049

  日期：2011.8

  FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of o-hydroxybenzylamines 1-16 and its corresponding new urea derivatives 17-32 were synthesized and fully characterized by spectroscopic methods and elemental analysis. This new urea derivatives class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-bromo-2-hydroxybenzyl)-1-(4-fluorophenyl)-3-phenylurea (18) and 1-(5-bromo-2-hydroxybenzyl)-1-(4-chlorophenyl)-3-phenylurea (20) were potent inhibitors of E. coli FabH. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• Synthesis and Biological Activity of Some 3-Aryl-3,4-dihydro-2H-benz[e]- 1,3-oxazines/6-bromo-3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines
  作者：Davender Kumar Shukla、Manju Rani、Arif Ali Khan、Kavita Tiwari、Rajinder K. Gupta

  DOI：10.14233/ajchem.2013.14091

  日期：——

  N-(2-Hydroxy)-benzyl-arylamine (1) gives substantially pure 3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines/6-bromo-3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines (2) on cyclization with formaldehyde in methanol within 0.5-1.0 h at 65-68 ºC in excellent yields. The compounds thus prepared were screened for their antimicrobial studies against Gram-positive bacteria (Staphylococcus aureus, MTCC 96) and Gram-negative bacteria (E. coli, MTCC 739). For estimating antifungal activity the organism used is Candida albicans. Minimum inhibitory concentration of all the compounds was determined using the micro-broth dilution method.

  N-(2-羟基)-苄基芳胺(1)在甲醇中与甲醛进行环化反应，在65-68°C下0.5-1.0小时内，可以高产率地得到几乎纯的3-芳基-3,4-二氢-2H-苯并[e]-1,3-恶嗪/6-溴-3-芳基-3,4-二氢-2H-苯并[e]-1,1-恶嗪(2)。这些化合物随后被用于针对革兰氏阳性细菌（金黄色葡萄球菌，MTCC 96）和革兰氏阴性细菌（大肠杆菌，MTCC 739）的抗菌活性研究。为了评估抗真菌活性，使用的真菌为白色念珠菌。所有化合物的最低抑制浓度是通过微量肉汤稀释法确定的。