N-(3-methoxy-4-hydroxybenzylidene)-p-toluidine | 53304-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(3-methoxy-4-hydroxybenzylidene)-p-toluidine
• 英文别名: (4-hydroxy-3-methoxybenzylidene)-p-tolyl amine；vanillidene-p-toluidine；3-methoxy-4-{[(4-methylphenyl)imino]methyl}phenol；2-methoxy-4-(p-tolylimino-methyl)-phenol；(4-Oxy-3-methoxy-benzal)-p-toluidin；Vanillin-p-tolylimid；Phenol, 2-methoxy-4-[[(4-methylphenyl)imino]methyl]-；2-methoxy-4-[(4-methylphenyl)iminomethyl]phenol
• CAS: 53304-12-4
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: WOHNYSCHFCWUAS-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  415.9±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-methoxy-4-hydroxybenzylidene)-p-toluidine 在 sodium tetrahydroborate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.0h， 生成 1-(4-Hydroxy-3-methoxybenzyl)-3-phenyl-1-p-tolylthiourea (2b)
  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
• 作为产物：
  描述：

  N-(对甲苯基)羟胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N-(3-methoxy-4-hydroxybenzylidene)-p-toluidine
  参考文献：
  名称：

  Rai, Mangat; Kumar, Surinder; Singh, Baldev, Journal of the Indian Chemical Society, 1982, vol. 59, # 1, p. 80 - 81

  摘要：

  DOI：

文献信息

• Chitosan: a highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions
  作者：Mohammad G. Dekamin、Mojtaba Azimoshan、Leila Ramezani

  DOI：10.1039/c3gc36901c

  日期：——

  Bronsted or Lewis acid centers – was found to be a highly efficient renewable and recoverable bio-polymer catalyst for the rapid and convenient synthesis of α-amino nitriles or imines from aromatic aldehydes and amines under mild reaction conditions at room temperature in high to quantitative yields. The α-amino nitrile derivatives were prepared through the Strecker reaction using trimethylsilyl cyanide

  商业的 壳聚糖 –未经任何活性的Bronsted或Lewis酸中心的后修饰–被发现是一种高效的可再生和可回收的生物聚合物 催化剂 用于快速方便地合成α-氨基 腈 或者 亚胺 来自芳香族 醛类 和 胺类在室温下在温和的反应条件下以高产率至定量产率。α-氨基腈衍生物是通过Strecker反应使用三甲基甲硅烷基氰化物 （TMSCN）并由 壳聚糖 作为非均相双功能有机催化剂。
• Al-Mamary, Mohammed; Abdelwahab, Siddig Ibrahim; Ali, Hapipah Mohd, Asian Journal of Chemistry, 2012, vol. 24, # 10, p. 4335 - 4339
  作者：Al-Mamary, Mohammed、Abdelwahab, Siddig Ibrahim、Ali, Hapipah Mohd、Ismail, Salma、Abdulla, Mahmood Ameen、Darvish, Pouya

  DOI：——

  日期：——
• Gopalakrishnan, Mannathusamy; Sureshkumar, Purushothaman; Kanagarajan, Vijayakumar, Journal of Chemical Research, 2005, # 5, p. 299 - 303
  作者：Gopalakrishnan, Mannathusamy、Sureshkumar, Purushothaman、Kanagarajan, Vijayakumar、Thanusu, Jeyaraman、Govindaraju, Ramalingam

  DOI：——

  日期：——
• Schmeyers, Jens; Toda, Fumio; Boy, Juergen, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 4, p. 989 - 993
  作者：Schmeyers, Jens、Toda, Fumio、Boy, Juergen、Kaupp, Gerd

  DOI：——

  日期：——
• Correlation studies in the oxidation of Vanillin Schiff bases by acid bromate - A kinetic and semi-empirical approach
  作者：T. Sathish、P. Ravi Teja、M. Parusha Ramudu、P. Sunitha Manjari、R. Koteshwar Rao

  DOI：10.1016/j.jics.2021.100233

  日期：2022.1