naphthalen-1-ylmethyl 4-methoxybenzoate | 145224-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: naphthalen-1-ylmethyl 4-methoxybenzoate
• CAS: 145224-15-3
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: YDHQVZDLYCDIRW-UHFFFAOYSA-N

物化性质

• 沸点：
  465.8±20.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 naphthalen-1-ylmethyl 4-methoxybenzoate 以70%的产率得到大茴香酸
  参考文献：
  名称：

  DeCosta, D. P.; Pincock, J. A., Canadian Journal of Chemistry, 1992, vol. 70, # 7, p. 1879 - 1885

  摘要：

  DOI：
• 作为产物：
  描述：

  1-萘甲醇 、 对甲氧基苯甲酰氯 在 吡啶 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 naphthalen-1-ylmethyl 4-methoxybenzoate
  参考文献：
  名称：

  DeCosta, D. P.; Pincock, J. A., Canadian Journal of Chemistry, 1992, vol. 70, # 7, p. 1879 - 1885

  摘要：

  DOI：

文献信息

• Pd‐Catalysed Decarbonylation Free Approach to Carbonylative Esterification of 5‐HMF to Its Aryl Esters Synthesis Using Aryl Halides and Oxalic Acid as C ₁ Source
  作者：Arvind Singh Chauhan、Ajay Kumar、Ajay Kumar Sharma、Pralay Das

  DOI：10.1002/chem.202101827

  日期：2021.9.9

  (Pd@PS)-catalysed carbonylative esterification of the hydroxy group of 5-hydroxymethyl furfural (5-HMF) to its corresponding aryl esters has been developed. The use of Pd@PS, oxalic acid as CO source, and aryl halides was first explored for the aryl ester of 5-HMF synthesis. Here, we investigated the vital role of a polystyrene support to avoid the commonly known decarbonylation of 5-HMF. The reaction

  已开发出无脱羰基、聚苯乙烯负载、Pd (Pd@PS) 催化的 5-羟甲基糠醛 (5-HMF) 羟基羰基化酯化反应生成相应的芳基酯。首次探索了使用 Pd@PS、草酸作为 CO 源和芳基卤化物来合成 5-HMF 的芳基酯。在这里，我们研究了聚苯乙烯载体的重要作用，以避免众所周知的 5-HMF 脱羰。该反应具有广泛的底物范围，具有相当好的收率和催化剂的可回收性。
• Hydroesterification and Difunctionalization of Olefins with <i>N</i>-Hydroxyphthalimide Esters
  作者：Lingying Leng、Joseph M. Ready

  DOI：10.1021/acscatal.1c03969

  日期：2021.11.5

  Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)3 in CH2Cl2. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates

  在未活化烯烃存在下辐照N-羟基邻苯二甲酰亚胺的芳基酯可促进温和的区域选择性加氢酯化。借助fac -Ir(dFppy) 3在 CH 2 Cl 2中获得最佳结果。末端和 1,1-二取代烯烃提供伯酯，三取代烯烃提供仲酯。抗马尔科夫尼科夫选择性与烷基自由基中间体一致，这也表明从二烯形成环化产物。单酰化二醇在水存在下由三取代和四取代烯烃形成。
• Benzylic C–H activation and C–O bond formation via aryl to benzylic 1,4-palladium migrations
  作者：Tanay Kesharwani、Richard C. Larock

  DOI：10.1016/j.tet.2008.01.144

  日期：2008.6

  A procedure for benzylic C-H activation has been developed using a palladium 1,4-aryl to benzylic migration as a key step. Carboxylates and phenoxides readily trap the resulting benzylic palladium intermediates obtained from palladium 'through space' migration. Aryl bromides and iodides have been successfully employed in this reaction, furnishing moderate to good yields. The mechanism of this reaction has been studied by deuterium-labeling experiments, which suggest that the migration of palladium from an aryl to a benzylic position occurs reversibly. The reaction conditions developed for the migration process also oxidize the neighboring benzylic alcohols to the corresponding aldehydes and ketones. (C) 2008 Elsevier Ltd. All rights reserved.
• Nickel-Catalyzed Selective Conversion of Two Different Aldehydes to Cross-Coupled Esters
  作者：Yoichi Hoshimoto、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1021/ja109908x

  日期：2011.4.6

  In the presence of a Ni(0)/NHC catalyst, an equimolar mixture of aliphatic and aryl aldehydes can be employed to selectively yield a single cross-coupled ester. This reaction can be applied to a variety of aliphatic (1 degrees, 2 degrees, cyc-2 degrees, and 3 degrees) and aryl aldehyde combinations. The reaction represents 100% atom efficiency and generates no waste. Mechanistic studies have revealed that the striking feature of the reaction is the simultaneous coordination of two aldehydes to Ni(0).