4-bromo-3,5-diethylphenol | 906623-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-3,5-diethylphenol
• CAS: 906623-15-2
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: QSFPEQVSTGLJFU-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  303.2±37.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-3,5-diethylphenol 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 生成 2',6'-diethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde
  参考文献：
  名称：

  Optimization of (2,3-Dihydro-1-benzofuran-3-yl)acetic Acids: Discovery of a Non-Free Fatty Acid-Like, Highly Bioavailable G Protein-Coupled Receptor 40/Free Fatty Acid Receptor 1 Agonist as a Glucose-Dependent Insulinotropic Agent

  摘要：

  G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) is a free fatty acid (FFA) receptor that mediates FFA-amplified glucose-stimulated insulin secretion in pancreatic beta-cells. We previously identified (2,3-dihydro-1-benzofuran-3-yl)acetic acid derivative 2 as a candidate, but it had relatively high lipophilicity. Adding a polar functional group on 2 yielded several compounds with lower lipophilicity and little effect on caspase-3/7 activity at 30 mu M (a marker of toxicity in human HepG2 hepatocytes). Three optimized compounds showed promising pharmacokinetic profiles with good in vivo effects. Of these, compound 16 had the lowest lipophilicity. Metabolic analysis of 16 showed a long-acting PK profile due to high resistance to beta-oxidation. Oral administration of 16 significantly reduced plasma glucose excursion and increased insulin secretion during an OGTT in type 2 diabetic rats. Compound 16 (TAK-875) is being evaluated in human clinical trials for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm300170m
• 作为产物：
  描述：

  4-乙基苯酚 在 aluminum (III) chloride 、 tetra-N-butylammonium tribromide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 4-bromo-3,5-diethylphenol
  参考文献：
  名称：

  Optimization of (2,3-Dihydro-1-benzofuran-3-yl)acetic Acids: Discovery of a Non-Free Fatty Acid-Like, Highly Bioavailable G Protein-Coupled Receptor 40/Free Fatty Acid Receptor 1 Agonist as a Glucose-Dependent Insulinotropic Agent

  摘要：

  G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) is a free fatty acid (FFA) receptor that mediates FFA-amplified glucose-stimulated insulin secretion in pancreatic beta-cells. We previously identified (2,3-dihydro-1-benzofuran-3-yl)acetic acid derivative 2 as a candidate, but it had relatively high lipophilicity. Adding a polar functional group on 2 yielded several compounds with lower lipophilicity and little effect on caspase-3/7 activity at 30 mu M (a marker of toxicity in human HepG2 hepatocytes). Three optimized compounds showed promising pharmacokinetic profiles with good in vivo effects. Of these, compound 16 had the lowest lipophilicity. Metabolic analysis of 16 showed a long-acting PK profile due to high resistance to beta-oxidation. Oral administration of 16 significantly reduced plasma glucose excursion and increased insulin secretion during an OGTT in type 2 diabetic rats. Compound 16 (TAK-875) is being evaluated in human clinical trials for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm300170m

文献信息

• Syntheses of Sterically Hindered Pyridinium Phenoxides as Model Compounds in Nonlinear Optics
  作者：Vincent Diemer、Hélène Chaumeil、Albert Defoin、Alain Fort、Alex Boeglin、Christiane Carré

  DOI：10.1002/ejoc.200600030

  日期：2006.6

  increase in the twist angle between the two aromatic rings leads to an enhancement of the NLO properties. In order to confirm this feature experimentally, it was necessary to prepare a series of new hindered pyridinium phenoxides. Their efficient syntheses by Suzuki cross-coupling reactions are described herein.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  具有 π 共轭系统的非中心对称分子，其中包括苯酚吡啶等推挽分子，由于其非线性光学 (NLO) 特性，是一类有前途的新型光电子材料。建模研究表明，两个芳环之间扭曲角的增加导致 NLO 性能的增强。为了通过实验证实这一特征，有必要制备一系列新的受阻吡啶酚盐。本文描述了它们通过 Suzuki 交叉偶联反应的有效合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• FUSED CYCLIC COMPOUNDS
  申请人：Yasuma Tsuneo

  公开号：US20100004312A1

  公开（公告）日：2010-01-07

  The present invention provides a compound represented by the formula (I): wherein each symbol is as defined in the description, or a salt thereof. The compound or a salt thereof or a prodrug thereof has a GPR40 receptor function modulating action and is useful as an insulin secretagogue or an agent for the prophylaxis or treatment of diabetes and the like.

  本发明提供一种化合物，其表示为公式（I）：其中每个符号如描述中所定义，或其盐。该化合物或其盐或其前药具有GPR40受体功能调节作用，并可用作胰岛素分泌剂或用于预防或治疗糖尿病等药物。
• Fused cyclic compounds
  申请人：Yasuma Tsuneo

  公开号：US20100197761A1

  公开（公告）日：2010-08-05

  The present invention provides a compound represented by the formula (I): wherein each symbol is as defined in the description, or a salt thereof. The compound or a salt thereof or a prodrug thereof has a GPR40 receptor function modulating action and is useful as an insulin secretagogue or an agent for the prophylaxis or treatment of diabetes and the like.

  本发明提供一种化合物，其化学式表示为（I）：其中每个符号如描述中所定义，或其盐。该化合物或其盐或其前药具有GPR40受体功能调节作用，并且可用作胰岛素分泌剂或预防或治疗糖尿病等疾病的药物。
• N-cyano- and N-alkynyl-2-(substituted phenoxy)butyramides and the use thereof as mildewicides
  申请人：STAUFFER CHEMICAL COMPANY

  公开号：EP0001721A2

  公开（公告）日：1979-05-02

  "N-cyano and N-alkynyl-2- (substituted phenoxy) butyramides and the use thereof as miidewicides" A compound corresponding to the following general formula: wherein O represents when Q represents X represents chlorine, bromine, thiocyano or methyl; and R represents methyl, ethyl or methoxymethyl; and when 0 represents X represents bromine or methyl; and R' represents hydrogen or methyl. The use of such compounds for controlling mildew is also disclosed.

  "N-氰基和 N-炔基-2-（取代的苯氧基）丁酰胺及其作为杀微生物剂的用途" 符合以下通式的化合物： 其中 O 代表 当 Q 代表 X 代表氯、溴、硫氰酸或甲基；R 代表甲基、乙基或甲氧基甲基；当 0 代表时 X 代表溴或甲基；R'代表氢或甲基。 还公开了此类化合物在控制霉菌方面的用途。
• Fused cyclic compounds as GPR40 receptor modulators
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2248812A2

  公开（公告）日：2010-11-10

  The present invention provides a pharmaceutical composition comprising a compound represented by the formula (I): wherein each symbol is as defined in the description, or a salt thereof, in combination with a dipeptidyl peptidase IV inhibitor, an insulin preparation, a PPAR function modulator, an α-glucosidase inhibitor, a biguanide, a sulfonylurea, mitiglinide or calcium salt hydrate thereof or nateglinide.

  本发明提供了一种药物组合物，其中包含由式 (I) 代表的化合物： 其中各符号如描述中所定义，或其盐与二肽基肽酶 IV 抑制剂、胰岛素制剂、PPAR 功能调节剂、α-葡萄糖苷酶抑制剂、双胍类、磺酰脲类、米格列奈或其钙盐水合物或纳格列奈联合使用。