2-phenylnaphtho[2,1-d]oxazole | 3574-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenylnaphtho[2,1-d]oxazole
• 英文别名: 2-Phenyl-naphth<2,1-d>oxazol；2-phenylbenzo[g][1,3]benzoxazole
• CAS: 3574-03-6
• 化学式: C₁₇H₁₁NO
• 分子量: 245.28
• InChiKey: FSGTWXWWYPZHTD-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(Solv: ligroine (8032-32-4))
• 沸点：
  397.0±11.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-1-萘酚 在 氢氧化钾 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 0.5h， 生成 2-phenylnaphtho[2,1-d]oxazole
  参考文献：
  名称：

  NEW SYNTHESIS OF NAPHTHO- AND BENZOXAZOLES: DECOMPOSITION OF NAPHTHO- AND BENZOXAZINONES WITH KOH

  摘要：

  A method that allows the synthesis of 4 different heterocyclic systems of fused aryl oxazoles, i.e., naphtho[1,2-d], naphtho[2,1-d], naphtho[2,3-d], and benzo[d]oxazoles in reasonable yield is del scribed. This method consists of the decomposition of naphtho- and benzoxazinones with KOH.

  DOI：

  10.1081/scc-100000190

文献信息

• Reaction of 1-Nitroso-2-naphthols with α-Functionalized Ketones and Related Compounds: The Unexpected Formation of Decarbonylated 2-Substituted Naphtho[1,2-<i>d</i>][1,3]oxazoles
  作者：Nayyef Aljaar、Chandi C. Malakar、Jürgen Conrad、Wolfgang Frey、Uwe Beifuss

  DOI：10.1021/jo3022956

  日期：2013.1.4

  Reactions between 1-nitroso-2-naphthols and α-functionalized ketones such as α-bromo-, α-chloro-, α-mesyloxy-, α-tosyloxy-, and α-hydroxy ketones under basic conditions delivered 2-substituted naphtho[1,2-d][1,3]oxazoles in a single synthetic operation. The product formation was accompanied by the unexpected loss of the C═O group from the α-functionalized ketones. With aryl bromides, allyl bromides

  1-亚硝基-2-萘与α-官能化酮如α-溴代，α-氯代，α-甲氧基，α-甲苯磺酰基和α-羟基酮之间的反应在碱性条件下产生了2-取代的萘并[一次合成操作中的1,2- d ] [1,3]恶唑。产物的形成伴随有α-官能化酮中C═O基团的意外损失。以芳基溴化物，烯丙基溴化物，α-溴二酮，α-溴氰化物，α-溴酸酯和α-溴酮酸酯为底物，还观察到了萘并[1,2- d ] [1,3]恶唑的形成。在回流下在1,2-二氯乙烷或乙腈中进行转化，得到相应的萘并恶唑，产率在52％至85％之间。
• Iron(0)-Catalyzed Transfer Hydrogenative Condensation of Nitroarenes with Alcohols: A Straightforward Approach to Benzoxazoles, Benzothiazoles, and Benzimidazoles
  作者：Ramachandra Reddy Putta、Simin Chun、Seung Hyun Choi、Seok Beom Lee、Dong-Chan Oh、Suckchang Hong

  DOI：10.1021/acs.joc.0c02191

  日期：2020.12.4

  the redox condensation of o-hydroxynitrobenzene with alcohol, leading to the formation of benzoxazole derivatives. A wide range of 2-substituted benzoxazoles were synthesized in good to excellent yields without the addition of an external redox agent. A series of control experiments provided a plausible mechanism. Furthermore, the reaction system was successfully extended to the synthesis of benzothiazoles

  铁催化的氢转移策略已经应用于邻羟基硝基苯与醇的氧化还原缩合，导致形成苯并恶唑衍生物。在不添加外部氧化还原剂的情况下，合成了范围广泛的2-取代的苯并恶唑，收率良好至优异。一系列对照实验提供了一个合理的机制。此外，该反应体系已成功扩展到苯并噻唑和苯并咪唑的合成。
• Oxazoles formation during<i>O</i>-alkylation of isonitroso-naphthols. X-ray structure of [1,2]naphthoquinone 1-[<i>O</i>-(4-<i>tert</i>-butyl-benzyl)-oxime] and 2-(4-<i>tert</i>-butyl-phenyl)napth[1,2-<i>d</i>]oxazole
  作者：Paola Astolfi、Patricia Carloni、Riccardo Castagna、Lucedio Greci、Pierluigi Stipa、Corrado Rizzoli

  DOI：10.1002/jhet.5570410618

  日期：2004.11

  and in the presence of triethylamine affording, in low yields, the corresponding O-benzyl oximes and 2-aryl naphthoxazoles in a 1:1 ratio, approximately. The structures of O-benzyl oximes and naphthoxazoles isolated have been determined by X-ray analysis.

  以亚硝基形式存在的1-亚硝基-2-萘酚和2-亚硝基-1-萘酚与苄基溴在THF中和在三乙胺存在下反应，以低收率得到相应的O-苄基肟和2-芳基萘并恶唑的比例约为1：1。通过X射线分析确定了分离的O-苄基肟和萘恶唑的结构。
• Photophysics and Photochemistry of Naphthoxazinone Derivatives
  作者：Santi Nonell、Lourdes R. Ferreras、Alvaro Cañete、Else Lemp、German Günther、Nancy Pizarro、Antonio L. Zanocco

  DOI：10.1021/jo800039r

  日期：2008.7.1

  The photophysics and photochemistry of a series of naphthoxazinones have been studied using a combination of methods ranging from steady-state and time-resolved spectroscopic techniques to product analysis. The photophysics of naphthoxazinone derivatives is very dependent on the structure: phenanthrene-like compounds exhibit higher fluorescence quantum yield than the less aromatic anthracene-like homologous. The latter, exhibit a substantial degree of charge transfer in the excited singlet state. These compounds are fairly photostable in the absence of additives, yielding a single photoproduct arising from the triplet state. The presence of electron donors such as amines increases the photoconsumption quantum yield and changes the product distribution, the primary photoproduct being a dihydronaphthoxazinone that photoreacts further yielding ultimately an oxazoline derivative.
• 83. Heterocyclic organoboron compounds. Part I. Five-membered ring systems from amino- and hydroxy-naphthalenes
  作者：R. Hemming、D. G. Johnston

  DOI：10.1039/jr9640000466

  日期：——