methyl 4-hydroxy-[1,1'-biphenyl]-2-carboxylate | 181268-43-9

• 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: methyl 4-hydroxy-[1,1'-biphenyl]-2-carboxylate
• 英文别名: methyl 4-hydroxybiphenyl-2-carboxylate；4-hydroxy-biphenyl-2-carboxylic acid methyl ester；Methyl4-hydroxy-[1,1-biphenyl]-2-carboxylate；methyl 5-hydroxy-2-phenylbenzoate
• CAS: 181268-43-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: SPUMIUSNTFZHOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  412.6±33.0 °C(predicted)
• 密度：
  1.194±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxy-[1,1'-biphenyl]-2-carboxylate 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 4-(2-Hydroxy-ethyl)-biphenyl-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A Novel Series of [2-[Methyl(2-phenethyl)amino]-2-oxoethyl]benzene-Containing Leukotriene B₄ Antagonists:  Initial Structure−Activity Relationships

  摘要：

  This report describes the synthesis of a new class of LTB(4) receptor antagonists containing [2-[methyl(2-phenethyl)amino]-2-oxoethyl]benzene as a key binding domain for interaction with high-affinity LTB(4) receptors. In addition to this binding domain, two other structural features, an acid function and a lipophilic group, are also required by these compounds for high binding affinity, Our studies indicate that maximal binding affinity in this series is controlled by the spatial relationship of these groups relative to one another, The structure-activity relationships are discussed, The most potent compound in this chemical series, (E)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (32), has an IC50 of 2 nM in a guinea pig spleen cell membrane assay, In the whale-cell human neutrophils binding assay, (Z)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (30) was the most potent compound with an IC50 of 50 nM.

  DOI：

  10.1021/jm9506985
• 作为产物：
  描述：

  3-苯基环戊-2-烯-1-酮 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 环丁砜 为溶剂， 反应 13.25h， 生成 methyl 4-hydroxy-[1,1'-biphenyl]-2-carboxylate
  参考文献：
  名称：

  双环[3.1.0]己-2-酮的开环：用于构建取代苯甲酸酯的多功能合成平台

  摘要：

  描述了使用双环[3.1.0] hexan-2-ones开发高效2π旋转开环芳构化序列的过程。这种前所未有的转变可在热条件下有效进行，并且可以轻松构建独特取代的多官能化苯甲酸酯。在胺或醇的存在下，分别形成取代的苯胺或醚。此外，该方法的实用性在短的癸二酸甲酯的合成中得到了证明。

  DOI：

  10.1002/anie.201506232

文献信息

• WO2007/58504
  申请人：——

  公开号：——

  公开（公告）日：——
• Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and γ-Phosphonyl Crotonates Mediated by Air: Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates
  作者：Prabhakar Ramchandra Joshi、Jagadeesh Babu Nanubolu、Rajeev S. Menon

  DOI：10.1021/acs.orglett.6b00016

  日期：2016.2.19

  Regioselective synthesis of 4-hydroxybiphenyl-2-carboxylates via the base-mediated oxygenative [3 + 3] benzannulation reaction of alpha,beta-unsaturated aldehydes and gamma-phosphonyl crotonates is reported. A hydroxyl group is installed in the final product on the originally phosphorus-bound carbon via a novel oxygenative and dehydrogenative transformation. The reaction proceeds rapidly in an open flask, uses atmospheric oxygen as an oxidant, and affords good yields of substituted biaryl phenols.
• [EN] NOVEL COMPOUNDS AS AGONIST FOR PPAR GAMMA AND PPAR ALPHA, METHOD FOR PREPARATION OF THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] NOUVEAUX COMPOSES UTILISES COMME AGONISTES DES PPAR GAMMA ET DES PPAR ALPHA, PROCEDE DE PREPARATION AFFERENT ET COMPOSITION PHARMACEUTIQUE LES RENFERMANT
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2007058504A1

  公开（公告）日：2007-05-24

  [EN] The present invention relates to novel compounds accelerating the activity of Peroxisome proliferator-activated receptor gamma (PPAR?) and alpha (PPARa), processes of preparing the same, and pharmaceutical compositions containing the same as an active agent.
  [FR] L'invention porte sur de nouveaux composés accélérant l'activité des récepteurs gamma (PPAR?) et alpha (PPARa) activés par les proliférateurs des péroxysomes, sur des procédés de préparation afférents et sur des compositions pharmaceutiques les renfermant en tant qu'agent actif.
• Ring Opening of Bicyclo[3.1.0]hexan‐2‐ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates
  作者：Johannes Feierfeil、Adriana Grossmann、Thomas Magauer

  DOI：10.1002/anie.201506232

  日期：2015.9.28

  Described is the development of a highly efficient 2π disrotatory ring‐opening aromatization sequence using bicyclo[3.1.0]hexan‐2‐ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively,

  描述了使用双环[3.1.0] hexan-2-ones开发高效2π旋转开环芳构化序列的过程。这种前所未有的转变可在热条件下有效进行，并且可以轻松构建独特取代的多官能化苯甲酸酯。在胺或醇的存在下，分别形成取代的苯胺或醚。此外，该方法的实用性在短的癸二酸甲酯的合成中得到了证明。
• A Novel Series of [2-[Methyl(2-phenethyl)amino]-2-oxoethyl]benzene-Containing Leukotriene B₄ Antagonists:  Initial Structure−Activity Relationships
  作者：Fu-Chih Huang、Wan-Kit Chan、Kevin J. Moriarty、Gregory Poli、Matthew M. Morrissette、Robert A. Galemmo、James D. Warus、William P. Dankulich、Charles A. Sutherland

  DOI：10.1021/jm9506985

  日期：1996.1.1

  This report describes the synthesis of a new class of LTB(4) receptor antagonists containing [2-[methyl(2-phenethyl)amino]-2-oxoethyl]benzene as a key binding domain for interaction with high-affinity LTB(4) receptors. In addition to this binding domain, two other structural features, an acid function and a lipophilic group, are also required by these compounds for high binding affinity, Our studies indicate that maximal binding affinity in this series is controlled by the spatial relationship of these groups relative to one another, The structure-activity relationships are discussed, The most potent compound in this chemical series, (E)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (32), has an IC50 of 2 nM in a guinea pig spleen cell membrane assay, In the whale-cell human neutrophils binding assay, (Z)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (30) was the most potent compound with an IC50 of 50 nM.