(3,5-Dimethoxyphenyl) naphthalene-2-carboxylate | 1004687-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3,5-Dimethoxyphenyl) naphthalene-2-carboxylate
• CAS: 1004687-09-5
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: PVYHZMRCIRDGTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯并恶唑 、 (3,5-Dimethoxyphenyl) 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86%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 、 3,5-二甲氧基苯基三氟甲磺酸酯 、 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64%的产率得到(3,5-Dimethoxyphenyl) 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

• 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.