4-(naphthalen-1-yliminomethyl)phenol | 93324-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(naphthalen-1-yliminomethyl)phenol
• 英文别名: 4-(Naphthalen-1-yliminomethyl)-phenol
• CAS: 93324-84-6
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: GWZBECWYBXRWNF-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189 °C(Solv: ethanol (64-17-5))
• 沸点：
  455.1±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(naphthalen-1-yliminomethyl)phenol 在 sodium 、 六氯环三磷腈 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以81%的产率得到hexa[4-(1-naphthyl iminomethyl)phenoxy]cyclotriphosphazene
  参考文献：
  名称：

  PREPARATION AND CHARACTERIZATION OF CHROMOPHOR GROUP CONTAINING CYCLOTRIPHOSPHAZENES: I IMINO CHROMOPHOR CARRYING SOME CYCLOTRIPHOSPHAZENES

  摘要：

  Some new substituted cyclotriphosphazenes were prepared by the reaction of hexachlorocyclotriphophazene and 4-hydroxy or 4'-hydroxy Schiff bases as 4'-hydroxybenzylideneaniline, 4'-hydroxy-4-chlorobenzylideneaniline, 4'-hydroxy-2-chlorobenzylidenaniline, 4'-hydroxy furfurylidenaniline, 4-hydroxybenzylidene-2'-methylaniline, 4-hydroxybenzylidene-2',6' dimethylaniline, 4-hydroxybenzylidene-2'-chloroaniline, 4-hydroxybenzylidenr4'-tert-butylaniline, 4'-hydroxybenzylidene-3,4-15-Crown-5-aniline. The structure of compounds with a general formula [NP(OC6H4CH=N-Ar)(2)](3) or [NP(OC6H4N=CH-Ar)(2)](3), was determined by IR, UV, H-1-NMR and elemental analysis. IR spectra of all compounds showed four characteristic bands located at 1633-1601 cm(-1) 1242-1150 cm(-1) 1278-1261 cm(-1) and 958-943 cm(1), respectively, corresponding to CH=N, P=N, P-N-P (asymmetric) and P-N-P (symmetric) vibrations. Characteristic UV bands,named as Band I, Band II, Band III and Band IV located at 346-308nm, 294-271nm, 262-216nm and 240-210nm respectively, are due to electronic transitions. The H-1-NMR spectra of 4-hydroxyfurfurylidene and the phosphazene derivative shows cis-trans izomerization below 305 degrees K and 295 degrees K.

  DOI：

  10.1080/10426509908031613
• 作为产物：
  描述：

  1-萘胺 、 对羟基苯甲醛 在 1-丁基-3-甲基咪唑二(三氟甲基磺酰)酰亚胺 作用下， 以 甲醇 为溶剂， 生成 4-(naphthalen-1-yliminomethyl)phenol
  参考文献：
  名称：

  新型s-三嗪衍生物的合成，表征以及抗增殖和凋亡诱导作用†

  摘要：

  在试图设计和合成一类新的抗肿瘤剂的，用于亲核取代的温和和生态友好的协议使用š嗪骨架，通过胺和席夫碱衍生物，已被开发出来。为了获得抗肿瘤活性，在体外筛选所有合成的化合物对人纤维肉瘤肿瘤细胞（HT-1080）和宫颈癌细胞系（HeLa）的细胞毒性，以及它们抑制癌细胞生长的能力。选定的s -triazine类似物（5c，5d和6c）已针对HT-1080癌细胞系的活性氧（ROS）特性，线粒体膜电位（MMP）和凋亡（AO / EtBr）活性进行了初步研究。的体外抗癌活性分析表明，所合成的化合物具有针对所测试的细胞系好/中等抑制活性相对于标准药物。理论研究结果也提供了证据，表明通过基于结构的设计，s-三嗪支架已被成功鉴定为优越的p53-MDM2抑制剂。

  DOI：

  10.1039/c7nj03348f

文献信息

• A Study of Anti-inflammatory Activity of Some Novel α-Amino Naphthalene and β-Amino Naphthalene Derivatives
  作者：Shalabh Sharma、Tripti Singh、Rajan Mittal、K. K. Saxena、Virendra Kishore Srivastava、Ashok Kumar

  DOI：10.1002/ardp.200500215

  日期：2006.3

  In the present study, some naphthalene derivatives have been synthesized by incorporating azetidinyl and thiazolidinyl moieties at its α‐ or β‐positions such as α‐(3‐chloro‐2‐oxo‐4‐substituted)aryl‐1‐azetidinyl)naphthalenes 6–10, α‐((substituted)aryl‐4‐oxo‐1,3‐thiazolidin‐3‐yl)naphthalenes 11–15, β‐(3‐chloro‐2‐oxo‐4‐substituted aryl‐1‐azetidinyl)naphthalenes 21–25, and β‐(substituted aryl‐4‐oxo‐1,

  在本研究中，一些萘衍生物是通过在其 α- 或 β- 位引入氮杂环丁烷基和噻唑烷基部分来合成的，例如 α-（3-氯-2-氧代-4-取代）芳基-1-氮杂环丁烷基）萘 6 -10, α - ((取代的) 芳基-4-氧代-1,3-噻唑烷-3-基) 萘 11-15, β- (3-氯-2-氧代-4-取代的芳基-1-氮杂环丁烷基)萘 21-25 和 β-（取代芳基-4-氧代-1,3-噻唑烷-3-基）萘 26-30。还筛选了这些化合物的急性毒性和抗炎和镇痛活性。还检查了显示出更好抗炎和镇痛活性的化合物的致溃疡倾向并进行环加氧酶测定。与标准药物保泰松和萘普生相比，发现两种化合物 12 和 28 表现出有效的抗炎活性。
• A simple and clean procedure for the synthesis of polyhydroacridine and quinoline derivatives: reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Zhao-Sen Zeng、Da-Qing Shi、Shu-Jiang Tu、Xian-Yong Wei、Zhi-Min Zong

  DOI：10.1016/j.tetlet.2005.08.091

  日期：2005.10

  A clean and simple synthesis of benzo[c]acridine, benzo[a]acridine, pyrido[2,3-c]acridine and benzo[f]quinoline derivatives was accomplished in good to excellent yields via the reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium catalyzed by TEBA. The structures were characterized by 1H NMR, IR and elemental analysis, and confirmed by X-ray diffraction study.

  通过席夫碱与1的反应，可以很好地收率很好地完成苯并[ c ] ac啶，苯并[ a ] ac啶，吡啶并[2,3- c ] ac啶和苯并[ f ]喹啉衍生物的清洁，简单合成。TEBA催化的水性介质中的3-二羰基化合物。通过1 H NMR，IR和元素分析对结构进行表征，并通过X射线衍射研究证实。
• Synthesis and Antimicrobial Evaluation of Some 4-Thiazolidinone Derivatives Containing Polynuclear Hydrocarbon
  作者：Neelam Verma、Raj Bhushan Singh、Kuldeep Singh

  DOI：10.14233/ajchem.2016.20066

  日期：——

  Some 4-thiazolidinone derivatives have also been known to be associated with several biological activities thus can be utilized as promising scaffold for developing analogues. Aryl aldehydes were treated with naphthylamine to yield corresponding Schiff’s bases. The Schiff’s bases were treated with thioacetic acid in the presence of anhydrous ZnCl2 to afford 4-thiazolidinone derivatives then all the compounds were characterized and evaluated for antibacterial and antifungal activity. Compounds having methoxy group at meta- and para-position, dimethylamino and hydroxyl group at para-position was found to be biologically active.

  已知一些 4-噻唑烷酮衍生物也具有多种生物活性，因此可用作开发类似物的支架。芳基醛经萘胺处理后生成相应的席夫碱。在无水氯化锌存在下，用硫代乙酸处理希夫碱，得到 4-噻唑烷酮衍生物，然后对所有化合物进行表征，并评估其抗菌和抗真菌活性。发现在元和对位上有甲氧基、二甲基氨基和对位上有羟基的化合物具有生物活性。
• Synthesis, characterization and study of polymeric iron(III) complexes with bidentate p-hydroxy Schiff bases as heterogeneous catalysts
  作者：Hanna S. Abbo、Salam J.J. Titinchi、Rajendra Prasad、Shri Chand

  DOI：10.1016/j.molcata.2004.09.007

  日期：2005.1

  spectra of the Schiff bases I and II observed between δ 8.45 and 8.55 ppm were observed upfield shifted in the spectra of the complexes. The catalytic properties of the coordination polymers as heterogeneous catalysts were examined by liquid phase hydroxylation of phenol using H2O2 as an oxidant. It was found that these complexes provide high TOF value for the hydroxylation of phenol by H2O2. The % phenol

  螯合的席夫碱配体4-（萘-1-亚甲基甲基）-苯酚（I）和4-（萘-2-亚氨基甲基）-苯酚（II）分别通过α-或β-萘胺与p的缩合得到。-羟基苯甲醛。螯合配体I和II与硝酸铁（III）在乙醇水溶液中的反应提供了新的配位聚合物配合物聚[Fe（C 10 H 7 -1-NCHC 6 H 4 4-O）3 ]（III）和聚-[Fe（C 10 H 7 2-NCHC 6 H 4 4-O）3 ]（IV）。Schiff碱及其铁（III）配合物通过各种物理化学技术进行了表征。化合物的化学式通过元素分析确定。发现这两个配体均充当双齿桥接配体并因此形成交联的六配位聚合物络合物。从配体和配合物的IR，1 H NMR和UV-Vis光谱数据确定了配位关系，其中由于对称的禁止的d-d跃迁，在472和466 nm处观察到一个新的弱谱带。在δ之间观察到的席夫碱I和II的1 H NMR光谱中的偶氮甲碱质子信号在配合物的光谱中观察到8
• A thermal study of some Schiff bases derivative of α-napthylamine
  作者：Shipra Baluja、Nirmal Pandya、Nayan Vekariya

  DOI：10.1134/s0036024408090355

  日期：2008.9

  Thermal analyses of some Schiff bases, derivative of alpha-napthylamine, were performed by the DSC, TG and DTA techniques. The thermograms were used to determine various kinetic parameters, such as the order of degradation (n), energy of activation (E), frequency factor (A), and entropy change (Delta S), by the Freeman-Carroll method.