3-苯基乙炔-苯甲酸 | 93866-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苯基乙炔-苯甲酸
• 英文名称: 3-(2-phenylethynyl)benzoic acid
• 英文别名: 3-(phenylethynyl)benzoic acid；3-phenylethynyl-benzoic acid；3-Phenylaethinyl-benzoesaeure
• CAS: 93866-50-3
• 化学式: C₁₅H₁₀O₂
• mdl: MFCD06740205
• 分子量: 222.243
• InChiKey: YVBDUPNCTBINKB-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  425.5±28.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  3-苯基乙炔-苯甲酸 在 lithium aluminium tetrahydride 作用下， 生成 [3-(2-phenylethynyl)phenyl]methanol
  参考文献：
  名称：

  Benzyl Tosylates. III. The Relative Conjugative Aptitudes of the Acetylenic and Ethylenic Bonds

  摘要：

  DOI：

  10.1021/ja01110a044
• 作为产物：
  描述：

  3-(2-(E)-phenylethenyl)-benzoic acid 在 四氯化碳 、 氢氧化钾 、 溴 作用下， 生成 3-苯基乙炔-苯甲酸
  参考文献：
  名称：

  Benzyl Tosylates. III. The Relative Conjugative Aptitudes of the Acetylenic and Ethylenic Bonds

  摘要：

  DOI：

  10.1021/ja01110a044

文献信息

• Alpha-helical mimetics
  申请人：Lessene Guillaume Laurent

  公开号：US20080153802A1

  公开（公告）日：2008-06-26

  Benzoyl urea derivatives that are alpha helical peptides mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting-moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralizing pro-survival Bcl-2 proteins. Use of benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also described.

  公开了模拟α螺旋肽的苯甲酰脲衍生物，这些衍生物模拟BH3-仅蛋白，含有它们的组合物，它们与细胞靶向基团的结合，以及它们在调节细胞死亡中的用途。苯甲酰脲衍生物能够结合并中和促生存的Bcl-2蛋白。还描述了在治疗和/或预防与细胞死亡失调相关的疾病或症状中使用苯甲酰脲衍生物。
• [EN] PIPERAZINE METABOTROPIC GLUTAMATE RECEPTOR 5 (MGLUR5) NEGATIVE ALLOSTERIC MODULATORS FOR ANXIETY/DEPRESSION<br/>[FR] PIPÉRAZINE UTILISÉE EN TANT QUE MODULATEURS ALLOSTÉRIQUES NÉGATIFS AGISSANT SUR LE RÉCEPTEUR MÉTABOTROPIQUE DU GLUTAMATE DE TYPE 5 (MGLUR5)
  申请人：WYETH CORP

  公开号：WO2009143404A1

  公开（公告）日：2009-11-26

  The present teachings relate to piperazine metabotropic glutamate receptor 5 (mGluR5) negative allosteric modulators having Formula (I); wherein the constituent variables are as defined herein. The present teachings further relate to methods for the preparation of the compounds, and to methods for using the compounds for treatment of diseases and disorders including schizophrenia, paranoia, depression, manic-depressive illness and anxiety.

  本发明的教导涉及具有公式（I）的哌嗪代谢型谷氨酸受体5（mGluR5）负变构调节剂；其中构成变量如本文所述定义。本发明的教导还涉及制备这些化合物的方法，以及使用这些化合物治疗包括精神分裂症、偏执症、抑郁症、躁郁症和焦虑症等疾病和失调的方法。
• [EN] ALPHA-HELICAL MIMETICS<br/>[FR] MIMÉTIQUES D'HÉLICE ALPHA
  申请人：EARCH THE WALTER AND ELIZA HAL

  公开号：WO2006002474A1

  公开（公告）日：2006-01-12

  Benzoyl urea derivatives that are alpha helical peptide mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralising pro-survival Bcl-2 proteins. Use of the benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also disclosed.

  本文揭示了α螺旋肽类似物的苯甲酰脲衍生物，这些类似物模拟BH3-only蛋白质，包含它们的组合物，它们与细胞靶向基团的结合，以及它们在调控细胞死亡中的用途。苯甲酰脲衍生物能够结合并中和促生存的Bcl-2蛋白。还揭示了苯甲酰脲衍生物在治疗和/或预防与细胞死亡失调相关的疾病或症状中的用途。
• Synthesis and characterization of a polymer-anchored palladium(II) Schiff base complex and its catalytic efficiency in phosphine-free Sonogashira coupling reactions
  作者：S. M. Islam、Sanchita Mondal、Anupam Singha Roy、Paramita Mondal、Manir Mobarak、Dildar Hossain、Palash Pandit

  DOI：10.1007/s11243-010-9328-3

  日期：2010.4

  A polymer-anchored Pd(II) Schiff base complex has been synthesized by reacting a polymeric amine with 2-pyridinecarboxaldehyde to get the polymer-anchored Schiff base, which was then reacted with palladium acetate. The catalyst was characterized by physicochemical and spectroscopic methods. It shows excellent catalytic activity in the Sonogashira coupling of phenylacetylene with aryl halides using triethylamine as a base and copper iodide as a co-catalyst in water under open air at 70 °C. We have also studied the effects of base and solvent on the coupling reaction. Sonogashira reactions of phenylacetylene with a variety of functionalized aryl halides were performed under the optimized reaction conditions. This catalyst gives excellent yields without the use of phosphine ligands. Further experiments showed that the catalyst can be used five times without much loss in the catalytic activity.

  合成了一种聚合物固定的Pd(II) Schiff碱复合物，该复合物是通过聚合物胺与2-吡啶甲醛反应得到的聚合物固定的Schiff碱，随后与醋酸钯反应。催化剂通过物理化学和光谱学方法进行了表征。它在水中于开放空气下，在70°C时，使用三乙胺作为碱和碘化铜作为助催化剂进行苯乙炔与芳基卤化物的Sonogashira偶联反应时表现出优异的催化活性。我们还研究了碱和溶剂对偶联反应的影响。在优化反应条件下，进行了苯乙炔与多种功能化芳基卤化物的Sonogashira反应。该催化剂在不使用膦配体的情况下，提供了优异的产率。进一步实验显示，该催化剂可以重复使用五次，而催化活性损失不大。
• Development of Dipeptidic<i>h</i>GPR54 Agonists
  作者：Christelle Doebelin、Isabelle Bertin、Séverine Schneider、Martine Schmitt、Jean-Jacques Bourguignon、Caroline Ancel、Valerie Simonneaux、Frédéric Simonin、Frédéric Bihel

  DOI：10.1002/cmdc.201600331

  日期：2016.10.6

  A series of dipeptides were designed as potential agonists of the human KiSS1‐derived peptide receptor (hGPR54). While the sequence Arg‐Trp‐NH2 was the most efficient in terms of affinity, we established a convergent synthetic strategy to optimize the N terminus. Using two successive Sonogashira cross‐coupling reactions on a solid‐supported peptide, we were able to introduce various alkynes at the

  设计了一系列二肽作为人类KiSS1衍生肽受体（h GPR54）的潜在激动剂。虽然就亲和力而言，序列Arg-Trp-NH 2是最有效的，但我们建立了一种收敛的合成策略来优化N末端。通过在固相支持的肽上进行两个连续的Sonogashira交叉偶联反应，我们能够在N末端引入各种炔烃，从而为h GPR54提供亚微摩尔亲和力的化合物。然而，功能测定表明苯甲酰化的二肽Bz-Arg-Trp-NH 2就激动性能而言，它是最有前途的化合物。有趣的是，在大鼠的血清和肝微粒体中，该化合物似乎都比内源性神经肽基索肽更稳定。还发现该化合物能够在雄性大鼠中诱导体内睾丸激素水平的显着增加。