3-(3-溴-4-羟基苯基)丙酸乙酯 | 250284-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-(3-溴-4-羟基苯基)丙酸乙酯
• 英文名称: ethyl 3-(3-bromo-4-hydroxyphenyl)propionate
• 英文别名: ethyl 3-(3-bromo-4-hydroxyphenyl)propanoate
• CAS: 250284-66-3
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 273.126
• InChiKey: UMQZAVTXBYEULT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-(3-溴-4-羟基苯基)丙酸乙酯 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 正丁基锂 、 (CuOTf)*toluene 、 氢气 、 sodium acetate 、 potassium carbonate 、 caesium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， -78.0~110.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 Acetic acid 4-[3-(2,4-dimethoxy-phenyl)-3-oxo-propyl]-2-{4-[3-(2,4-dimethoxy-phenyl)-3-oxo-propyl]-2-methoxy-phenoxy}-phenyl ester
  参考文献：
  名称：

  Effects of a verbenachalcone derivative on neurite outgrowth, inhibition of caspase induction and gene expression

  摘要：

  A verbenachalcone derivative was synthesized and shown to protect N2a cells from caspase induction caused by serum starvation and to enhance the effect of NGF on neurite outgrowth in PC12 cells. As an initial investigation of the compound's mechanism(s) of action, we performed differential gene expression profiling in PC12 cells using oligonucleotide (similar to10,000 gene probes) microarrays. Gene expression patterns were compared in the presence of NGF (2 and 50 ng/mL) and NGF (2 ng/mL) plus the verbenachalcone derivative. Ten genes were significantly (greater than or equal to 2-fold; p less than or equal to 0.05) up-regulated and seven genes were significantly down-regulated in the presence of the compound. These results were independently validated by quantitative real-time PCR for a subset of genes (cathepsin L, sigma-1 receptor and protein tyrosine phosphatase receptor type R). These genes or their protein products may represent useful therapeutic targets for treating neurodegeneration, such as Alzheimer's disease. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.001
• 作为产物：
  描述：

  对羟基苯丙酸乙酯 在 溴 、 溶剂黄146 作用下， 反应 0.5h， 以85%的产率得到3-(3-溴-4-羟基苯基)丙酸乙酯
  参考文献：
  名称：

  铜催化的二芳基醚合成在制备马鞭草酮中的应用

  摘要：

  在吡啶中碳酸铯存在下，利用催化铜介导的2-苄氧基溴苯衍生物和2-甲氧基苯酚衍生物的偶合反应，有效地组装了2-羟基-2'-甲氧基二苯基醚。利用该方法可以简明合成马鞭草酚酮，该化合物据报道可增强神经生长因子刺激PC12D细胞中神经突生长的能力。还显示了初始SAR数据。

  DOI：

  10.1016/s0040-4020(02)00915-8

文献信息

• Substituted phenylalkanoic acid derivatives and use thereof
  申请人：——

  公开号：US20040044258A1

  公开（公告）日：2004-03-04

  A compound represented by the formula (I) or a salt thereof: 1 wherein n represents an integer of 1 to 3, R represents an alkyl group having 3 to 8 carbon atoms, a group represented by the following formula: R 1 (CH 2 ) k — (wherein k represents 0 or an integer of 1 to 3; R 1 represents a saturated cyclic alkyl group having 3 to 7 carbon atoms or a saturated condensed cyclic alkyl group having 6 to 8 carbon atoms, and the group R 1 may be substituted with a lower alkyl group having 1 to 4 carbon atoms) and the like, and Ar represents a condensed bicyclic group such as naphthalen-1-yl group, which has suppressing action on prostaglandin and leukotriene production and is useful for prophylactic and/or therapeutic treatment of various inflammatory diseases and the like caused by these lipid mediators.

  化合物的化学式为（I）或其盐： 其中n表示1到3的整数，R表示具有3到8个碳原子的烷基基团，由以下化学式表示的基团：R1(CH2)k—（其中k表示0或1到3的整数；R1表示具有3到7个碳原子的饱和环烷基基团或具有6到8个碳原子的饱和紧凑环烷基基团，基团R1可以被具有1到4个碳原子的较低烷基基团取代）等，Ar表示如萘-1-基团等的紧凑双环基团，具有对前列腺素和白三烯生成的抑制作用，对由这些脂质介质引起的各种炎症性疾病等的预防和/或治疗治疗有用。
• [EN] ISOTHIAZOLE DERIVATIVES AS GPR120 AGONISTS FOR THE TREATMENT OF TYPE II DIABETES<br/>[FR] DÉRIVÉS ISOTHIAZOLE UTILES EN TANT QU'AGONISTES DE GPR120 POUR LE TRAITEMENT DU DIABÈTE DE TYPE II
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2015134039A1

  公开（公告）日：2015-09-11

  Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR120 receptor. Such compounds are represented by Formula (I) as follows: wherein R1, G, and Q are defined herein.

  揭示了一种通过调节GPR120受体而影响的疾病的化合物、组合物和治疗方法。这些化合物由以下式（I）表示：其中R1、G和Q在此处定义。
• A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents
  作者：Xiaofeng Ma、Joshua J. Farndon、Tom A. Young、Natalie Fey、John F. Bower

  DOI：10.1002/anie.201708176

  日期：2017.11.13

  A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

  概述了具有广泛范围的 CN 键形成脱芳构化方案。具体来说，双功能氨基试剂用于顺序亲核和亲电CN键形成，后者影响关键的脱芳构化步骤。使用这种方法，只需两到三个步骤即可将 γ-芳基化醇转化为各种差异保护的螺环吡咯烷。
• A general synthetic route towards bastadins. Part 1: Synthesis of the eastern part of bastadins 4–16
  作者：Elias A. Couladouros、Vassilios I. Moutsos

  DOI：10.1016/s0040-4039(99)01429-x

  日期：1999.9

  A general synthetic route for the construction of the eastern part of the macrocyclic bastadins 4–16 is presented. The brominated biaryl ethers are synthesized using the iodonium salt method. The synthesis is accomplished within 18 steps in 15.5% overall yield.

  提出了大环Bastadins 4-16东部的一般合成路线。使用碘鎓盐方法合成溴化的联芳基醚。该合成在18个步骤内完成，总产率为15.5％。
• Utilization of a copper-catalyzed diaryl ether synthesis for the preparation of verbenachalcone
  作者：Xuechao Xing、Deepa Padmanaban、Li-An Yeh、Gregory D Cuny

  DOI：10.1016/s0040-4020(02)00915-8

  日期：2002.9

  2-Hydroxy-2′-methoxydiphenyl ethers were efficiently assembled utilizing a catalytic copper mediated coupling of 2-benzyloxybromobenzene derivatives and 2-methoxyphenol derivatives in the presence of cesium carbonate in pyridine followed by debenzylation. Utilization of this method allowed for a concise synthesis of verbenachalcone, a compound reported to enhance nerve growth factor's ability to stimulate

  在吡啶中碳酸铯存在下，利用催化铜介导的2-苄氧基溴苯衍生物和2-甲氧基苯酚衍生物的偶合反应，有效地组装了2-羟基-2'-甲氧基二苯基醚。利用该方法可以简明合成马鞭草酚酮，该化合物据报道可增强神经生长因子刺激PC12D细胞中神经突生长的能力。还显示了初始SAR数据。