1,4-dimethyl-2-naphthol | 4705-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dimethyl-2-naphthol
• 英文别名: 1,4-Dimethyl-[2]naphthol；2-Hydroxy-1.4-dimethyl-naphthalin；1,4-dimethyl-2-naphthalenol；1,4-Dimethyl-<2>naphthol；1,4-Dimethylnaphthalen-2-ol
• CAS: 4705-94-6
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: INBDACYHPDXEOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  135.5°C
• 沸点：
  315.5°C (estimate)
• 密度：
  0.9900 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-dimethyl-2-naphthol 在 锌 作用下， 生成 1,4-二甲基萘
  参考文献：
  名称：

  Cannizzaro; Carnelutti, Gazzetta Chimica Italiana, 1882, vol. 12, p. 406,413

  摘要：

  DOI：
• 作为产物：
  描述：

  8-Hydroxy-3,6,9-trimethyl-3a,4,5,9b-tetrahydro-3H-naphtho[1,2-b]furan-2-one 在 potassium carbonate 作用下， 生成 1,4-dimethyl-2-naphthol
  参考文献：
  名称：

  Bertolo, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1902, vol. <5> 11 I, p. 490

  摘要：

  DOI：

文献信息

• Isolation of Cyclohexadienone Intermediates in the Photo-Fries Rearrangement of 2,4-Dimethylnaphth-1-yl and 1,4-Dimethylnaphth-2-yl 2,4,6-Trimethylbenzoates
  作者：Tadashi Mori、Makoto Takamoto、Hideaki Saito、Takahiro Furo、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1246/cl.2004.254

  日期：2004.3

  Labile cyclohexadienones were isolated for the first time in good yields in the photo-Fries rearrangement of partially blocked naphthyl esters. Upon direct excitation at 313 nm, 1,4-dimethylnaphth-2-yl and 2,4-dimethylnaphth-1-yl 2,4,6-trimethylbenzoates afforded 1-acyl-2-naphthalenone and 2- and 4-acyl-1-naphthalenones, respectively. This isolation is of particular importance as a direct mechanistic

  在部分封闭的萘酯的 photo-Fries 重排中，首次以良好的产率分离出不稳定的环己二烯酮。在 313 nm 处直接激发后，1,4-二甲基萘-2-基和 2,4-二甲基萘-1-基 2,4,6-三甲基苯甲酸酯得到 1-酰基-2-萘酮和 2-和 4-酰基-1 -萘酮，分别。这种隔离作为直接的机械证据以及作为这些热不易接近的化合物的便捷途径特别重要。
• Functionalization of the methyl group of 1,4-dimethyl-1,4-dihydronaphthalene-1,4-endoperoxide
  作者：Charles W. Jefford、Jean-Claude Rossier、Shigeo Kohmoto、John Boukouvalas

  DOI：10.1039/c39840001496

  日期：——

  The acid-catalysed cleavage of 1,4-dimethyl-1,4-dihydronaphthalene-1,4-endoperoxide gives the 4-hydroxy, methoxy, trifluoroacetoxy, formyloxy, bromo, and chloro methyl derivatives of 1-methylnaphthalene in yields of 36,38,52,76,77, and 100% respectively when water, methanol, trifluoracetic, formic, hydrobromic, or hydrochloric acids are used as reagents.

  1,4-二甲基-1,4-二氢萘-1,4-内过氧化物的酸催化裂解反应生成1-甲基萘的4-羟基，甲氧基，三氟乙酰氧基，甲酰氧基，溴和氯甲基衍生物，收率为36，当使用水，甲醇，三氟乙酸，甲酸，氢溴酸或盐酸作为试剂时，分别为38,52,76,77和100％。
• Acid-Catalyzed Cleavage of 1,4-Dimethyl-1,4-dihydronaphthalene 1,4-Endoperoxide. Reactivity of the Resulting Hydroperoxy Carbocation with Nucleophiles
  作者：Charles W. Jefford、Jean-Claude Rossier、Shigeo Kohmoto、John Boukouvalas

  DOI：10.1002/hlca.19850680635

  日期：1985.9.25

  In the presence of acids, 1,4-dimethyl-1,4-dihydronaphthalene 1,4-endoperoxide readily reacts with nucleophiles to produce methyl- and ring-substituted naphthalenes in high yields. The regioselectivity observed depends on the nucleophile. The key intermediate is shown to be the corresponding hydroperoxy carbocation which could be intercepted in certain cases prior to aromatization. The hydroperoxide

  在酸的存在下，1,4-二甲基-1,4-二氢萘1,4-内过氧化物容易与亲核试剂反应，以高收率生产甲基和环取代的萘。观察到的区域选择性取决于亲核试剂。关键中间体显示为相应的氢过氧碳正离子，在某些情况下，芳构化之前可能会截获该氢。氢过氧化物也经历霍克型裂解和二聚化，得到2,3-二氢-1-苯并氧杂环丁烷，4-甲基-1-萘酚和1,2,5,6-四氧杂环己烷作为副产物。
• Remarkable Differences in Photo and Thermal (Acid-catalyzed) Reactivities between<i>ortho</i>- and<i>para</i>-Acylcyclohexadienones as Essential Factors Determining the Overall Efficiency of the Photo-Fries Rearrangement
  作者：Tadashi Mori、Makoto Takamoto、Hideaki Saito、Takahiro Furo、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1246/cl.2004.256

  日期：2004.3

  Successful isolation of “ortho” and “para”-acylcyclohexadienones allowed us to comparatively study their ground- and excited-state behavior under a variety of conditions. In neutral solutions, the two isomeric cyclohexdienones showed completely different reactivities for photochemical and thermal reactions, while in acidic methanol both quantitatively afforded the corresponding transesterification product and naphthol. These studies help us understand the detailed photo-Fries rearrangement mechanism, which involves several crucial photochemical and thermal steps.

  成功分离出 "正 "和 "对 "酰基环己二烯酮后，我们得以比较研究它们在各种条件下的基态和激发态行为。在中性溶液中，这两种异构环己二烯酮在光化学反应和热反应中表现出完全不同的反应活性，而在酸性甲醇中，这两种环己二烯酮都能定量生成相应的酯交换产物和萘酚。这些研究有助于我们了解详细的光-弗里斯重排机理，其中涉及几个关键的光化学和热反应步骤。
• Rhodium-Catalyzed Asymmetric Cyclodimerization of Oxabenzonorbornadienes and Azabenzonorbornadienes:  Scope and Limitations
  作者：Anna Allen、Paul Le Marquand、Ryan Burton、Karine Villeneuve、William Tam

  DOI：10.1021/jo7012884

  日期：2007.10.1

  Cationic rhodium(I)-catalyzed cyclodimerization of oxabenzonorbornadienes produced naphtho[1,2-b]furan ring systems in a single step with excellent yields and excellent enantioselectivities. The effect of various Rh(I) catalysts, Ag(I) salts, solvents, and phosphine ligands on the yield and enantioselectivity of the reaction was investigated, and the scope and limitations of this reaction with various

  阳离子铑（I）催化的氧杂苯并降冰片二烯环二聚反应可一步合成萘[1,2- b ]呋喃环系统，并具有优异的收率和出色的对映选择性。研究了各种Rh（I）催化剂，Ag（I）盐，溶剂和膦配体对反应收率和对映选择性的影响，并研究了该反应与各种恶双环烯的范围和局限性。用氮杂苯并降冰片二烯类似物获得了相似的结果，以优异的产率和优异的对映选择性提供了相应的环二聚产物。