ethyl 4-hydroxy-[1,1'-biphenyl]-3-carboxylate | 17504-14-2

• 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: ethyl 4-hydroxy-[1,1'-biphenyl]-3-carboxylate
• 英文别名: ethyl 2-hydroxy-5-phenylbenzoate；ethyl 4-hydroxy-biphenyl-3-carboxylate；4-hydroxy-biphenyl-3-carboxylic acid ethyl ester；4-Hydroxy-biphenyl-3-carbonsaeure-aethylester；4-Hydroxy-3-ethoxycarbonylbiphenyl；Ethyl-5-phenylsalicylat；Ethyl 5-phenylsalicylate
• CAS: 17504-14-2
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: WFDNZBPCPYBMIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  ethyl 4-hydroxy-[1,1'-biphenyl]-3-carboxylate 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 丙酮 为溶剂， 生成 2-hydroxy-5-phenylacetophenone
  参考文献：
  名称：

  Synthesis of ethyl 6-substituted-chroman- and -chromone-2-carboxylates. Comparative structure-activity study employing the 6-phenyl and phenoxy analogs in the triton hyperlipidemic rat model

  摘要：

  To explore the effect of lipophilicity on antilipidemic activity in the Triton WR-1339 induced hyperlipidemic rat model we synthesized the 6-cyclohexyl, phenyl, and phenoxy analogs of ethyl chroman-2-carboxylate. Results obtained were analyzed in light of the biological activity observed for the 6-chloro-substituted and unsubstituted chromans, the 6-chlorochroman-4-one ester, and the 6-chloro-, phenyl-, and phenoxychromone esters. The suggestion is made that chromones likely exert their antilipidemic effects by a somewhat different set of mechanisms than do the chromans and clofibrate. Whereas the 6-chlorochromanone ester is inactive, the 6-chlorochromone ester is active in both normal and hyperlipidemic Sprague-Dawley rats. The major differential effect was observed for ethyl 6-cyclohexylchroman-2-carboxylate which did not lower cholesterol levels but returned triglyceride levels to normal in hyperlipidemic rats.

  DOI：

  10.1021/jm00243a015
• 作为产物：
  描述：

  对羟基联苯 在 硫酸 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 ethyl 4-hydroxy-[1,1'-biphenyl]-3-carboxylate
  参考文献：
  名称：

  Synthesis of ethyl 6-substituted-chroman- and -chromone-2-carboxylates. Comparative structure-activity study employing the 6-phenyl and phenoxy analogs in the triton hyperlipidemic rat model

  摘要：

  To explore the effect of lipophilicity on antilipidemic activity in the Triton WR-1339 induced hyperlipidemic rat model we synthesized the 6-cyclohexyl, phenyl, and phenoxy analogs of ethyl chroman-2-carboxylate. Results obtained were analyzed in light of the biological activity observed for the 6-chloro-substituted and unsubstituted chromans, the 6-chlorochroman-4-one ester, and the 6-chloro-, phenyl-, and phenoxychromone esters. The suggestion is made that chromones likely exert their antilipidemic effects by a somewhat different set of mechanisms than do the chromans and clofibrate. Whereas the 6-chlorochromanone ester is inactive, the 6-chlorochromone ester is active in both normal and hyperlipidemic Sprague-Dawley rats. The major differential effect was observed for ethyl 6-cyclohexylchroman-2-carboxylate which did not lower cholesterol levels but returned triglyceride levels to normal in hyperlipidemic rats.

  DOI：

  10.1021/jm00243a015

文献信息

• Highly efficient thermal cyclization reactions of alkylidene esters in continuous flow to give aromatic/heteroaromatic derivatives
  作者：László Lengyel、Tibor Zs. Nagy、Gellért Sipos、Richard Jones、György Dormán、László Ürge、Ferenc Darvas

  DOI：10.1016/j.tetlet.2011.11.125

  日期：2012.2

  Intramolecular thermal cyclization and benzannulation reactions of the Gould–Jacobs and Conrad–Limpach types were performed in a designed continuous flow reactor system at temperatures in the range of 300–360 °C and under high pressure conditions (100–160 bar) with very short residence times (0.45–4.5 min) in tetrahydrofuran as a low-boiling point solvent. Substituted heteroaromatic compounds including

  Gould–Jacobs和Conrad–Limpach类型的分子内热环化和苯环化反应在设计的连续流反应器系统中在300–360°C的温度范围内和高压条件下（100–160 bar），非常短的时间内进行在四氢呋喃中作为低沸点溶剂的停留时间（0.45-4.5分钟）。以中等至高收率合成了取代的杂芳族化合物，包括吡啶并嘧啶酮和羟基喹啉。应用反应条件还可以合成萘酚和联苯衍生物。该过程涉及容易的后处理，并且非分批制备的合成方法适合于自动化。
• Oxidative [3+3] Annulation of Atropaldehyde Acetals with 1,3‐Bisnucleophiles: An Efficient Method of Constructing Six‐Membered Aromatic Rings, Including Salicylates and Carbazoles
  作者：Yanlong Gu、Fengtian Wu、Jian Yang

  DOI：10.1002/adsc.201800462

  日期：2018.7.16

  Alkyl acetoacetates, α‐(indol‐2‐yl)acetate, anilines, 1‐methyl‐1H‐pyrazol‐3‐amine, ethyl 5‐amino‐1H‐pyrazole‐3‐carboxylate, and 3‐amino‐1H‐indazole can all be used as 1,3‐bisnucleophiles in this type of transformation. The established reactions can very efficiently construct six‐membered aromatic rings, including salicylates and carbazoles. A four‐step method of synthesizing the anti‐inflammatory agent

  使用N-溴代琥珀酰亚胺或溴化铜（II）作为氧化剂，并使用布朗斯台德酸或路易斯酸作为催化剂，开发了具有各种1,3-双亲核试剂的氧化乙醛缩醛[3 + 3] 。从机械上讲，[3 + 3]圆环可以看作是通过自动串联催化概念建立的氧化试剂诱导的酸-酸催化的多米诺反应。乙酰乙酸烷基酯，α-（吲哚-2-基）乙酸酯，苯胺，1-甲基-1 H-吡唑-3-胺，5-氨基-1 H-吡唑-3-羧酸乙酯和3-氨基-1 H在这种类型的转化中，吲唑都可以用作1,3-双亲核试剂。既定的反应可以非常有效地构建六元芳环，包括水杨酸酯和咔唑。基于氧化性[3 + 3]环化反应，还开发了一种合成抗炎剂二氟乙醛的四步法，收率很高。
• Difluorocarbene-Mediated Cascade Cyclization: The Multifunctional Role of Ruppert–Prakash Reagent
  作者：Yanyao Cai、Wenjie Zhu、Shujuan Zhao、Chanjuan Dong、Zhenchuang Xu、Yanchuan Zhao

  DOI：10.1021/acs.orglett.1c00962

  日期：2021.5.7

  bipolar CF2 building block, which enables a homologation cyclization process via sequentially reacting with the phenolate and the ester group on the same substrate. The potential application of this synthetic approach is demonstrated by a late-stage modification of diethylstilbestrol. Mechanistic studies revealed the multiple crucial roles played by the Ruppert–Prakash reagent.

  用于快速访问甲二氟卡宾体介导级联环化反应偕-二氟化的3-香豆冉酮衍生物被开发。二氟卡宾用作双极CF 2构件，可通过与同一底物上的酚盐和酯基顺序反应来实现同源环化过程。己烯雌酚的后期修饰证明了这种合成方法的潜在应用。机理研究表明，Ruppert-Prakash试剂具有多种关键作用。
• Process for vertical alignment of rod-like liquid crystal molecules
  申请人：——

  公开号：US20030003246A1

  公开（公告）日：2003-01-02

  A process for alignment of rod-like liquid crystal molecules comprises the steps of: forming an orientation layer for vertical alignment on a support; and forming a liquid crystal layer containing rod-like liquid crystal molecules on the orientation layer to align the rod-like liquid crystal molecules at an average inclined angle of 50 to 90°. The liquid crystal layer further contains a compound represented by the formula (I): (Hb-L 1 -Cy 1 -L 2 -) n Cy 2 (I) wherein Hb is an aliphatic group having 6 to 40 carbon atoms or an siloxanoxy group substituted with an aliphatic group having 6 to 40 carbon atoms, each of L 1 and L 2 is a single bond or a divalent linking group, Cy 1 is a divalent aromatic group or a divalent heterocyclic group, n is 2, 3 or 4, and Cy 2 is an n-valent aromatic group or an n-valent heterocyclic group.

  一种用于排列棒状液晶分子的过程，包括以下步骤：在支撑物上形成垂直排列的取向层；在取向层上形成含有棒状液晶分子的液晶层，以将棒状液晶分子排列成平均倾斜角度为50至90°。液晶层进一步含有以下化合物(I)的化合物：(Hb-L1-Cy1-L2-)nCy2(I)，其中，Hb是具有6至40个碳原子的脂肪基或被具有6至40个碳原子的脂肪基取代的硅氧烷基，L1和L2各自是单键或二价连接基，Cy1是二价芳香族基或二价杂环基，n为2、3或4，Cy2是n价芳香族基或n价杂环基。
• Liquid crystal composition comprising liquid crystal molecules and alignment promoter
  申请人：——

  公开号：US20020039627A1

  公开（公告）日：2002-04-04

  A liquid crystal composition comprises liquid crystal molecules and an alignment promoter. The alignment promoter is represented by the formula (I). ( Hb - L 1 -) n Bl  (I) In the formula (I), Hb is an aliphatic group having 4 to 40 carbon atoms, an aromatic group having 6 to 40 carbon atoms or an aliphatic substituted oligosiloxanoxy group having 1 to 40 carbon atoms. L 1 is a single bond or a divalent linking group, and n is an integer of 2 to 12. Bl is an n-valent group comprising at least two rings.

  一种液晶组合物包括液晶分子和取向促进剂。该取向促进剂由式(I)表示。(Hb-L1-)nBl  (I)在式(I)中，Hb是具有4至40个碳原子的脂肪族基，具有6至40个碳原子的芳香族基或具有1至40个碳原子的脂肪族取代的寡硅氧烷氧基。L1是单键或二价连接基，n是2至12的整数。Bl是至少包含两个环的n价基团。