2-methoxyphenyl naphthalene-2-carboxylate | 926786-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxyphenyl naphthalene-2-carboxylate
• 英文别名: (2-Methoxyphenyl) naphthalene-2-carboxylate
• CAS: 926786-74-5
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: DUMNPFSFZBNBTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  苯并恶唑 、 2-methoxyphenyl naphthalene-2-carboxylate 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以81%的产率得到2-萘-2-基-1,3-苯并恶唑
  参考文献：
  名称：

  Decarbonylative C–H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A

  摘要：

  A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.

  DOI：

  10.1021/ja306062c
• 作为产物：
  描述：

  一氧化碳 、 三氟甲磺酸2-甲氧基苯基酯 、 2-萘酚 在 palladium diacetate 、 potassium carbonate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 90.0 ℃ 、300.01 kPa 条件下， 反应 48.0h， 以68%的产率得到2-methoxyphenyl naphthalene-2-carboxylate
  参考文献：
  名称：

  Palladium-catalyzed carbonylative transformation of phenols via in-situ triflyl exchangement

  摘要：

  Phenols are attractive starting materials due to their ready availability. Herein, we developed a novel method on palladium-catalyzed alkoxycarbonylation of phenols. By using commercially available Pd(OAc)(2) and PtBu center dot HBF4 as the catalyst system and aryl triflates as triflyl source to activate the other phenol, various carboxylic acid esters were prepared in moderate to good yields via Tf exchange and then O-Tf bond cleavage. Notably, phenols generated from aryl triflates after Tf transfer or other additional aliphatic alcohols can all be employed as nucleophiles to synthesize the corresponding esters. (C) 2020 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2020.06.034

文献信息

• Molybdenum Hexacarbonyl Mediated Alkoxycarbonylation of Aryl Halides
  作者：Motoki Yamane、Wei Ren、A. Emi

  DOI：10.1055/s-0030-1260060

  日期：2011.7

  Mo(CO)6-mediates the alkoxycarbonylation of aryl halides in their reaction with alcohols to afford arenecarboxylic acid esters. The molybdenum carbonyl complexes act as the catalyst and the source with carbon monoxide. The alkoxycarbonylation proceeds with a small excess of carbon monoxide in the form of Mo(CO)6 and the procedure is simple compared to the conventional method, which uses palladium catalyst

  Mo（CO）6-在芳基卤化物与醇的反应中介导芳基卤化物的烷氧基羰基化，提供芳烃羧酸酯。羰基钼配合物充当一氧化碳的催化剂和来源。烷氧基羰基化反应以少量过量的Mo（CO）6形式的一氧化碳进行，与常规方法相比，该方法比较简单，该常规方法在气态一氧化碳下使用钯催化剂。使用该程序，制备了各种羧酸酯。 钼-羰基配合物-羰基化-酯化-酰化
• Decarbonylative C–H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
  作者：Kazuma Amaike、Kei Muto、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1021/ja306062c

  日期：2012.8.22

  A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.
• Palladium-catalyzed carbonylative transformation of phenols via in-situ triflyl exchangement
  作者：Hai Wang、Youcan Zhang、Chong-Liang Li、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2020.06.034

  日期：2020.9

  Phenols are attractive starting materials due to their ready availability. Herein, we developed a novel method on palladium-catalyzed alkoxycarbonylation of phenols. By using commercially available Pd(OAc)(2) and PtBu center dot HBF4 as the catalyst system and aryl triflates as triflyl source to activate the other phenol, various carboxylic acid esters were prepared in moderate to good yields via Tf exchange and then O-Tf bond cleavage. Notably, phenols generated from aryl triflates after Tf transfer or other additional aliphatic alcohols can all be employed as nucleophiles to synthesize the corresponding esters. (C) 2020 Elsevier Inc. All rights reserved.