1-octadecylnaphthalen-2-ol | 142531-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-octadecylnaphthalen-2-ol
• 英文别名: 1-Octadecyl-[2]naphthol
• CAS: 142531-50-8
• 化学式: C₂₈H₄₄O
• 分子量: 396.657
• InChiKey: ZQSCYHVJORPXEQ-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 amalgamated zinc 作用下， 生成 1-octadecylnaphthalen-2-ol
  参考文献：
  名称：

  Desai; Waravdekar, Proceedings - Indian Academy of Sciences, Section A, 1946, vol. 23, p. 341,343,344

  摘要：

  DOI：

文献信息

• Ruthenium‐Catalyzed Selective α‐Alkylation of β‐Naphthols using Primary Alcohols: Elucidating the Influence of Base and Water
  作者：Raman Vijaya Sankar、Abra Mathew、Subham Pradhan、Rositha Kuniyil、Chidambaram Gunanathan

  DOI：10.1002/chem.202302102

  日期：2023.10.23

  Functionalized arenes and arenols have diverse applications in chemical synthesis and material chemistry. Selective functionalization of arenols is a topic of prime interest. In particular, direct alkylation of arenols using alcohols is a challenging task. In this report, a ruthenium pincer catalyzed direct α‐alkylation of β‐naphthol using primary alcohols as alkylating reagents is reported. Notably, aryl and heteroaryl methanols and linear and branched aliphatic alcohols underwent selective alkylation reactions, in which water is the only byproduct. Notably, catalytically derived α‐alkyl‐β‐naphthol products displayed high absorbance, emissive properties, and quantum yields (up to 93.2 %). Dearomative bromination on α‐alkyl‐β‐naphthol is demonstrated as a synthetic application. Mechanistic studies indicate that the reaction involves an aldehyde intermediate. DFT studies support this finding and further reveal that a stoichiometric amount of base is required to make the aldol condensation as well as elementary steps required for regeneration of catalytically active species. In situ‐generated water molecule from the aldol condensation reaction plays an important role in the regeneration of an active catalyst.

  摘要官能化的壬烷和壬醇在化学合成和材料化学中有着广泛的应用。壬醇的选择性官能化是人们最感兴趣的话题。特别是使用醇对壬醇进行直接烷基化是一项具有挑战性的任务。在本报告中，报告了以伯醇为烷基化试剂催化 β-萘酚的钌钳直接 α-烷基化反应。值得注意的是，芳基和杂芳基甲醇以及直链和支链脂肪醇发生了选择性烷基化反应，其中水是唯一的副产物。值得注意的是，催化生成的 α-烷基-β-萘酚产品具有很高的吸光度、发射性和量子产率（高达 93.2%）。对 α-烷基-β-萘酚的溴化反应被证明是一种合成应用。机理研究表明，该反应涉及一个醛中间体。DFT 研究支持这一发现，并进一步揭示了醛醇缩合反应需要一定量的碱，以及催化活性物质再生所需的基本步骤。醛醇缩合反应原位生成的水分子在活性催化剂的再生过程中发挥了重要作用。