2-(allyloxy)naphthalene | 3698-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(allyloxy)naphthalene
• 英文别名: Naphthalene, 2-(2-propenyloxy)-；2-prop-2-enoxynaphthalene
• CAS: 3698-15-5
• 化学式: C₁₃H₁₂O
• mdl: MFCD00043547
• 分子量: 184.238
• InChiKey: JHEKBCPEJKZQIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  2-(allyloxy)naphthalene 在 四(三苯基膦)钯 polymethylhydrosiloxane 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2-萘酚
  参考文献：
  名称：

  使用聚甲基氢硅氧烷-ZnCl 2 / Pd（PPh 3）4选择性地裂解烯丙基醚，胺和酯

  摘要：

  在温和条件下实现烯基脱保护以从相应的烯丙基醚，胺和酯中释放出游离的羟基，氨基和酸基。用于该转化的试剂组合是聚甲基氢硅氧烷（PMHS），ZnCl 2和Pd（PPh 3）4。

  DOI：

  10.1016/s0040-4020(01)00187-9
• 作为产物：
  描述：

  3-Bromoprop-2-enyl β-naphthyl ether 在 samarium diiodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 3.0h， 以92%的产率得到2-(allyloxy)naphthalene
  参考文献：
  名称：

  Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals

  摘要：

  Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals. Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(pi-exo)exo, 6-(pi-endo)exo, and 6-(pi-exo)exo mode, respectively. Radical 7 undergoes competitive 1,5-hydrogen translocation. Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively. Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent beta-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation. Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization). Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group. Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. alpha-Oxy(and alpha-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.

  DOI：

  10.1021/jo00128a013

文献信息

• Studies on Antifungal Agents. Part 22. 3-aryl-5-[(aryloxy)alkyl]-3-[(1H-imidazol-1-yl)methyl]-2-methylisoxazolidines and related derivatives
  作者：George B. Mullen、Patricia A. Swift、David M. Marinyak、Stanley D. Allen、Jeffrey T. Mitchell、C. Richard Kinsolving、Vassil St. Georgiev

  DOI：10.1002/hlca.19880710406

  日期：1988.6.15

  The synthesis and antifungal activity of a novel series of 3-aryl-5-[(aryloxy)alkyl]-3-[(1H-imidazol-1-yl)-methyl]-2-methylisoxazolidines and related compounds, are discussed. The synthesis of the title compounds was accomplished via a 1,3-dipolar cycloaddition of α-substituted ketonitrones with l-alkenyl phenyl ethers (Scheme 2 and 3). The compounds were evaluated for in vitro antifungal activity in

  讨论了一系列新的3-芳基-5-[（芳氧基）烷基] -3-[（1 H-咪唑-1-基）-甲基] -2-甲基异恶唑烷和相关化合物的合成和抗真菌活性。标题化合物的合成是通过α-取代的酮硝酮与1-烯基苯基醚的1，3-偶极环加成反应完成的（方案2和3）。评价了该化合物在固体琼脂培养物中对多种酵母和全身性真菌病和皮肤真菌的体外抗真菌活性。虽然在整个系列中都有明显的抗真菌活性，但一般来说，芳基环中一个或两个都具有卤素原子的衍生物显示出最高的效力，特别是对毛癣菌和白色念珠菌。发现二氯类似物20（PR 967-248）具有最有用的活性。与标准药物酮康唑（0.2）相比，其最小抑菌浓度（MIC）值介于0.2和2.0μg/ ml之间（4）。
• Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity
  作者：Keary M. Engle、Lukas Pfeifer、George W. Pidgeon、Guy T. Giuffredi、Amber L. Thompson、Robert S. Paton、John M. Brown、Véronique Gouverneur

  DOI：10.1039/c5sc01812a

  日期：——

  The X-ray structures of fourteen novel fluoride–alcohol complexes with tetrabutylammonium as the counterion show coordination diversity varying from four to two depending on the steric bulk of the alcohol.

  十四种新颖的氟化物-醇络合物的X射线结构，以四丁基铵作为对离子，显示出协调多样性，取决于醇的立体位阻。
• Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
  作者：Zi Hui、Songwei Jiang、Xiang Qi、Xiang-Yang Ye、Tian Xie

  DOI：10.1016/j.tetlet.2020.151995

  日期：2020.6

  The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates

  对微波加速烯丙基芳基醚的克莱森重排进行了研究，以便深入了解催化剂，溶剂，温度和底物的范围。在所考察的催化剂中，发现磷钼酸（PMA）在220至300°C的温度下可大大促进NMP中的反应。发现该方法对于使用贵金属催化剂例如Au（I），Ag（I）和Pt（II）制备先前在文献中报道的几种中间体是有用的。另外，在芳基部分带有溴和硝基的底物需要仔细调整反应条件，以避免复杂的产物分布。
• Reductive C–O, C–N, and C–S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach
  作者：Christof Matt、Frederic Kölblin、Jan Streuff

  DOI：10.1021/acs.orglett.9b02572

  日期：2019.9.6

  A zirconium catalyzed reductive cleavage of Csp3 and Csp2 carbon-heteroatom bonds is reported that makes use of a tethered alkene functionality as a traceless directing group. The reaction is successfully demonstrated on C-O, C-N, and C-S bonds and proposed to proceed via a hydrozirconation/β-heteroatom elimination sequence of an in situ formed zirconium hydride catalyst. The positional isomerization

  据报道锆对Csp3和Csp2碳-杂原子键的催化还原裂解，利用链状烯烃官能团作为无痕导向基团。该反应已在CO，CN和CS键上成功证明，并建议通过原位形成的氢化锆催化剂的加氢锆/β-杂原子消除顺序进行。催化剂的位置异构化还能够裂解均烯丙基醚并除去末端的烯丙基和炔丙基。
• Practical, mild and efficient electrophilic bromination of phenols by a new I(<scp>iii</scp>)-based reagent: the PIDA–AlBr₃system
  作者：Yuvraj Satkar、Velayudham Ramadoss、Pradip D. Nahide、Ernesto García-Medina、Kevin A. Juárez-Ornelas、Angel J. Alonso-Castro、Ruben Chávez-Rivera、J. Oscar C. Jiménez-Halla、César R. Solorio-Alvarado

  DOI：10.1039/c8ra02982b

  日期：——

  Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.

  在高效且非常温和的反应条件下开发了一种实用的苯酚和苯酚醚亲电溴化方法。研究了广泛的芳烃，包括苯并咪唑和咔唑核心以及萘普生和扑热息痛等止痛药。新型 I( III ) 基溴化试剂PhIOAcBr通过混合 PIDA 和 AlBr 3易于制备。我们的 DFT 计算表明，这可能是溴化活性物质，它是原位制备的或离心后分离的。制备后 1 个月内证实其在 4°C 下的稳定性，未观察到其反应性显着损失。此外，2-萘酚的克级溴化反应具有优异的产率。即使对于空间位阻底物，也观察到适度良好的反应性。