3-(4-联苯基)丙酸 | 35888-99-4

• 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-(4-联苯基)丙酸
• 中文别名: 3-(4-联苯)丙酸
• 英文名称: 3-(4-biphenylyl)propionic acid
• 英文别名: 3-[(1,1'-biphenyl)-4-yl]propanoic acid；3-(4-biphenyl)propanoic acid；-([1,1′-biphenyl]-4-yl)propanoic acid；3-([1,1′-biphenyl]-4-yl)propionic acid；3-(4-Phenylphenyl)propanoic acid
• CAS: 35888-99-4
• 化学式: C₁₅H₁₄O₂
• mdl: MFCD06823979
• 分子量: 226.275
• InChiKey: MVFHRQWYCXYYMU-UHFFFAOYSA-N

物化性质

• 熔点：
  149-152℃
• 沸点：
  400.4±24.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下应存于干燥密封的环境中。

反应信息

• 作为反应物：
  描述：

  3-(4-联苯基)丙酸 在 palladium diacetate 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 生成 3-(4-(5-(2-([1,1'-biphenyl]-4-yl)ethyl)-1,3,4-oxadiazol-2-yl)phenyl)acrylic acid
  参考文献：
  名称：

  1,3,4-Oxadiazole-Containing Histone Deacetylase Inhibitors: Anticancer Activities in Cancer Cells

  摘要：

  We describe 1,3,4-oxadiazole-containing hydroxamates (2) and 2-aminoanilides (3) as histone deacetylase inhibitors. Among them, 2t, 2x, and 3i were the most potent and selective against HDAC1. In U937 leukemia cells, 2t was more potent than SAHA in inducing apoptosis, and 3i displayed cell differentiation with a potency similar to MS-275. In several acute myeloid leukemia (AML) cell lines, as well as in U937 cells in combination with doxorubicin, 3i showed higher antiproliferative effects than SAHA.

  DOI：

  10.1021/jm500303u
• 作为产物：
  描述：

  4-联苯乙酸 在 lithium aluminium tetrahydride 、 四溴化碳 、 magnesium 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-(4-联苯基)丙酸
  参考文献：
  名称：

  The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols

  摘要：

  The enantioselectivity of the lipase from Pseudomonas cepacia (PCL) in the transesterification of 2-phenyl-1-propanol I was studied using a series of vinyl 3-arylpropanoates as acyl donors. The most enantioselective transesterification reaction of the alcohol was attained by using vinyl 3-(p-iodophenyl)- or 3-(p-trifluoromethylphenyl)propanoates, with enantiomer ratios, E, of 116 and 138, respectively. Vinyl 3-phenylpropanoate was also effective for the resolution of 1 mediated by lipases from P. fluorescens and porcine pancreas and for the PCL-catalysed transesterification of several 2-phenyl-1-alkanols. The enantiomeric resolution of 1 was practically carried out by the first enantioselective transesterification using PCL and vinyl 3-(p-iodophenyl)propanoate to afford (R)-1 and then the enantioselective hydrolysis of the resultant ester to afford (S)-1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00083-0

文献信息

• α-Ketoheterocycles Able to Inhibit the Generation of Prostaglandin E2 (PGE2) in Rat Mesangial Cells
  作者：Anastasia Psarra、Maria A. Theodoropoulou、Martin Erhardt、Marina Mertiri、Christiana Mantzourani、Sofia Vasilakaki、Victoria Magrioti、Andrea Huwiler、George Kokotos

  DOI：10.3390/biom11020275

  日期：——

  Prostaglandin E2 (PGE2) is a key mediator of inflammation, and consequently huge efforts have been devoted to the development of novel agents able to regulate its formation. In this work, we present the synthesis of various α-ketoheterocycles and a study of their ability to inhibit the formation of PGE2 at a cellular level. A series of α-ketobenzothiazoles, α-ketobenzoxazoles, α-ketobenzimidazoles, and α-keto-1,2,4-oxadiazoles were synthesized and chemically characterized. Evaluation of their ability to suppress the generation of PGE2 in interleukin-1β plus forskolin-stimulated mesangial cells led to the identification of one α-ketobenzothiazole (GK181) and one α-ketobenzoxazole (GK491), which are able to suppress the PGE2 generation at a nanomolar level.

  前列腺素E2（PGE2）是炎症的关键介质，因此人们已经付出了巨大的努力来开发能够调节其形成的新型药物。在这项工作中，我们介绍了各种α-酮杂环的合成，并研究它们抑制细胞水平PGE2形成的能力。合成了一系列α-酮苯并噻唑、α-酮苯并噁唑、α-酮苯并咪唑和α-酮-1,2,4-噁二唑，并进行了化学表征。评估它们在白细胞介素-1β加福尔斯科林刺激的系膜细胞中抑制PGE2生成的能力，发现了一种α-酮苯并噻唑（GK181）和一种α-酮苯并噁唑（GK491），它们能够在纳摩尔水平上抑制PGE2的生成。
• A Ligand-Directed Catalytic Regioselective Hydrocarboxylation of Aryl Olefins with Pd and Formic Acid
  作者：Wei Liu、Wenlong Ren、Jingfu Li、Yuan Shi、Wenju Chang、Yian Shi

  DOI：10.1021/acs.orglett.7b00507

  日期：2017.4.7

  An effective Pd-catalyzed hydrocarboxylation of aryl olefins with Ac2O and formic acid is described. A variety of 2- and 3-arylpropanoic acids can be regioselectively formed by the judicious choice of ligand without the use of toxic CO gas.

  描述了用Ac 2 O和甲酸有效地Pd催化芳基烯烃的加氢羧化反应。通过明智地选择配体可以在不使用有毒CO气体的情况下区域选择性地形成各种2-和3-芳基丙酸。
• Structure–Activity Relationship of a New Series of Reversible Dual Monoacylglycerol Lipase/Fatty Acid Amide Hydrolase Inhibitors
  作者：José A. Cisneros、Emmelie Björklund、Inés González-Gil、Yanling Hu、Ángeles Canales、Francisco J. Medrano、Antonio Romero、Silvia Ortega-Gutiérrez、Christopher J. Fowler、María L. López-Rodríguez

  DOI：10.1021/jm201327p

  日期：2012.1.26

  (30) stand out as potent inhibitors of human recombinant MAGL (IC50 (8) = 4.1 μM; IC50 (30) = 2.4 μM), rat brain monoacylglycerol hydrolysis (IC50 (8) = 1.8 μM; IC50 (30) = 0.68 μM), and rat brain FAAH (IC50 (8) = 5.1 μM; IC50 (30) = 0.29 μM). Importantly, and in contrast to the other previously described MAGL inhibitors, these compounds behave as reversible inhibitors either of competitive (8) or noncompetitive

  两种内源性大麻素，anandamide（AEA）和2-arachidonoylglycerol（2-AG）在体内发挥独立和非冗余的作用。这使得选择性和双重灭活抑制剂的开发成为重要的优先事项。在这项工作中，我们报告了一系列新的单酰基甘油脂肪酶（MAGL）和脂肪酸酰胺水解酶（FAAH）抑制剂。其中，（±）-环氧乙烷-2-基甲基6-（1,1'-联苯-4-基）己酸（8）和（2 R）-（-）-环氧乙烷-2-基甲基（4-苄基苯基）乙酸盐（30）作为人类重组MAGL（IC 50（8）= 4.1μM ; IC 50（30）= 2.4μM ），大鼠脑单酰基甘油水解（IC 50（8）= 1.8μM; IC 50（30）= 0.68μM）和大鼠脑FAAH（IC 50（8）= 5.1μM; IC 50（30）= 0.29μM）。重要的是，与其他先前描述的MAGL抑制剂相反，这些化合物具有竞争性（8）或非竞争性（3
• Amine compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06329389B1

  公开（公告）日：2001-12-11

  The present invention provides a compound of the formula: wherein Ar represents an aromatic group which may be substituted; X represents methylene, S, SO, SO2 or CO; Y represents a spacer having a main chain of 2 to 5 atoms; n represents an integer of 1 to 5; i) R1 and R2 each represents a hydrogen atom or a lower alkyl which may be substituted, ii) R1 and R2 form, taken together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic ring which may be substituted, or iii) R1 or R2 together with —(CH2)n—N═ form, bonded to a component atom of Ring B, a spiro-ring which may be substituted; Ring A represents an aromatic ring which may be substituted; Ring B represents a 4- to 7-membered nitrogen-containing non-aromatic ring which may be further substituted by alkyl or acyl, with a proviso that X represents S, SO, SO2 or CO when Ring A has as a substituent a group represented by the formula: —NHCOR11 where R11 represents alkyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or a group represented by the formula: —NHR12 where R12 represents alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or a salt thereof; which has an excellent somatostatin receptor binding inhibition action.

  本发明提供了一种化合物，其化学式如下： 其中Ar代表可能被取代的芳香基团； X代表亚甲基、S、SO、SO2或CO； Y代表具有2到5个原子的主链的间隔物； n代表1到5的整数； i）R1和R2分别代表氢原子或可能被取代的较低烷基， ii）R1和R2与相邻的氮原子一起形成可能被取代的含氮杂环环，或 iii）R1或R2与—(CH2)n—N═一起形成，与环B的一个组分原子结合，可能被取代的螺环； 环A代表可能被取代的芳香环； 环B代表可能被烷基或酰基进一步取代的4到7成员的含氮非芳香环， 但有一个条件是，当环A具有由下式表示的基团作为取代基时： —NHCOR11 其中R11代表烷基、烷氧基烷基、烷硫基烷基、环烷基、环烷基烷基、芳基、芳基烷基或由下式表示的基团： —NHR12 其中R12代表烷基、环烷基、环烷基烷基、芳基或芳基烷基，或其盐；具有优异的生长抑素受体结合抑制作用。
• Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel‐Catalyzed Direct Decarbonylative Borylation
  作者：Xi Deng、Jiandong Guo、Xiaofeng Zhang、Xiaotai Wang、Weiping Su

  DOI：10.1002/anie.202106356

  日期：2021.11.8

  A Ni-catalyzed direct decarbonylative borylation of aryl carboxylic acids with B2cat2 has been established. B2cat2 serves as a borylating agent, but also activates the carboxylic acid substrate towards decarbonylative coupling, playing a dual role in this reaction. A combination of experimental and computational studies reveals that the reaction proceeds through a hitherto unknown concerted decarbonylation

  已经建立了镍催化的芳基羧酸与 B 2 cat 2 的直接脱羰硼酰化反应。B 2 cat 2作为硼酸化剂，但也活化羧酸底物以进行脱羰偶联，在该反应中发挥双重作用。实验和计算研究的结合表明，该反应通过迄今为止未知的协同脱羰和还原消除步骤进行。