methyl 6-((methylsulfonyl)oxy)-2-naphthoate | 161912-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-((methylsulfonyl)oxy)-2-naphthoate
• 英文别名: 6-Carbomethoxy-2-naphthyl methanesulfonate；methyl-6-methanesulfonyloxy-β-naphthoate；methyl 6-methylsulfonyloxynaphthalene-2-carboxylate
• CAS: 161912-37-4
• 化学式: C₁₃H₁₂O₅S
• 分子量: 280.301
• InChiKey: KICCNVFMLQQOLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-((methylsulfonyl)oxy)-2-naphthoate 在 bis(triphenylphosphine)nickel(II) chloride 、 四乙基碘化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到6,6'-Dicarbomethoxy-2,2'-dinaphthyl
  参考文献：
  名称：

  Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates

  摘要：

  Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.

  DOI：

  10.1021/jo00106a031
• 作为产物：
  描述：

  6-羟基-2-萘甲酯 、 甲基磺酰氯 在 吡啶 作用下， 以84%的产率得到methyl 6-((methylsulfonyl)oxy)-2-naphthoate
  参考文献：
  名称：

  Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates

  摘要：

  Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.

  DOI：

  10.1021/jo00106a031

文献信息

• Novel compounds and their use in medicine,as antidiabetic and hypolipidemic agents, process for their preparation and pharmaceutical compositions containing them
  申请人：Debnath Bhunia

  公开号：US20070093476A1

  公开（公告）日：2007-04-26

  The present invention relates to novel compounds of formula (I) and their pharmaceutically acceptable salts, wherein ring “Ar 1 ” represents a monocyclic or polycyclic aromatic or partially saturated aromatic polycyclic, which may optionally contain up to 3 heteroatoms selected from N, S or O. The said monocyclic or polycyclic ring may be unsubstituted or have up to 4 substituents which may be identical or different; m and n independently represents an integer from 0 to 6; A represents O, S or bond; Y is selected from (CH 2 ) p′ (CH 2 ) p B(CH 2 ) q′ (CH 2 ) r B(CH 2 ) p D(CH 2 ) p′ where p, q and r each independently represents an integer from 0 to 6; B and D independently represents S, O, NR 4 or a bond, with a proviso that when B and D represents hereto atom p is not zero; R 4 represents hydrogen, alkyl, alkenyl, —S(O) 2 —R 8 or —C(O)R 8 where R 8 is alkyl, alkoxy; R 5 and R 6 independently represents hydrogen, alkyl, cycloalkyl or alkoxy; R 5 and R 6 together may form 3-8 membered cyclic ring which may optionally contains one or two hereto atoms selected from O, S or N; R 7 represents hydrogen, optionally substituted groups selected form alkyl, cycloalkyl, alkenyl or alkynyl. The present invention also relates to a process for preparation of compounds of formula (I), to pharmaceutical compositions containing compounds of formula (I) and their use in particular as antidiabetic, hypolipidemic, antiobesity and hypocholesterolemic agents.

  本发明涉及公式（I）的新化合物及其药学上可接受的盐，其中环“Ar1”表示单环或多环芳香或部分饱和芳香多环，可选含有最多3个选自N、S或O的杂原子。所述的单环或多环环可以未取代或具有最多4个相同或不同的取代基；m和n分别表示0到6的整数；A表示O、S或键；Y选自（CH2）p′（CH2）pB（CH2）q′（CH2）rB（CH2）pD（CH2）p′，其中p、q和r各自独立地表示0到6的整数；B和D分别表示S、O、NR4或键，条件是当B和D表示杂原子时，p不为零；R4表示氢、烷基、烯基、—S（O）2—R8或—C（O）R8，其中R8为烷基、烷氧基；R5和R6各自独立地表示氢、烷基、环烷基或烷氧基；R5和R6可以一起形成3-8成员环，该环可以选择性地包含选自O、S或N的一个或两个杂原子；R7表示氢、可选地从烷基、环烷基、烯基或炔基中选择的取代基。本发明还涉及公式（I）化合物的制备方法，含有公式（I）化合物的制药组合物以及其作为抗糖尿病、降脂、抗肥胖和降胆固醇药物的应用。
• [EN] NOVEL COMPOUNDS AND THEIR USE AS ANTIDIABETIC AND HYPOLIPIDEMIC AGENTS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX COMPOSES ET LEUR UTILISATION EN MEDECINE, LEUR PROCEDE DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：REDDYS LAB LTD DR

  公开号：WO2005040102A3

  公开（公告）日：2006-03-23
• Cross-Coupling of Mesylated Phenol Derivatives with Potassium Cyclopropyltrifluoroborate
  作者：Gary A. Molander、Floriane Beaumard、Terren K. Niethamer

  DOI：10.1021/jo2015246

  日期：2011.10.7

  C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%.
• Percec Virgil, Bae Jin-Young, Zhao Mingyang, Hill Dale H., J. Org. Chem, 60 (1995) N 1, S 176-185
  作者：Percec Virgil, Bae Jin-Young, Zhao Mingyang, Hill Dale H.

  DOI：——

  日期：——
• 10.1016/j.tet.2024.134120
  作者：Zhao, Yan、Wu, Guo-Jie、Tan, Dong-Xing、Han, Fu-She

  DOI：10.1016/j.tet.2024.134120

  日期：——