2-Ethyl-4-carboxy-anisol | 22934-35-6

• 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: 2-Ethyl-4-carboxy-anisol
• 英文别名: 3-ethyl-4-methoxybenzoic acid；3-ethyl-p-anisic acid
• CAS: 22934-35-6
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: FPHXIFFANOEDCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-Ethyl-4-carboxy-anisol 在 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3-乙基-4-羟基苯甲酸甲酯
  参考文献：
  名称：

  Begue,J.-P.; Fetizon,M., Bulletin de la Societe Chimique de France, 1969, p. 781 - 787

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基苯酚 在 sodium hydroxide 、 溴 作用下， 以 甲醇 、 硝基苯 为溶剂， 生成 2-Ethyl-4-carboxy-anisol
  参考文献：
  名称：

  Begue,J.-P.; Fetizon,M., Bulletin de la Societe Chimique de France, 1969, p. 781 - 787

  摘要：

  DOI：

文献信息

• Phenyl urea and phenyl thiourea derivatives as HFGAN72 antagonists
  申请人：SmithKline Beecham p.l.c.

  公开号：US06410529B1

  公开（公告）日：2002-06-25

  Phenyl urea and phenylthiourea derivatives, processes for their production and their uses as pharmaceuticals are disclosed.

  苯基脲和苯基硫脲衍生物的生产过程以及它们作为药物的用途被披露。
• Benzothiophenes, benzofurans, and indoles useful in the treatment of insulin-resistance and hyperglycemia
  申请人：——

  公开号：US20020002187A1

  公开（公告）日：2002-01-03

  This invention provides compounds of Formula I having the structure 1 A is hydrogen, halogen, or OH; B and D are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyaralkyl of 6-12 carbon atoms, cycloalkyl of 3-8 carbon atoms, nitro, amino, —NR 1 R 1a , —NR 1 COR 1a , —NR 1 CO 2 R 1a , cycloalkylamino of 3-8 carbon atoms, morpholino, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, —COR 1b or OR; R is hydrogen, alkyl of 1-6 carbon atoms, —COR 1 , —(CH 2 ) n CO 2 R 1 , —CH(R 1a )CO 2 R 1 , —SO 2 R 1 , —(CH 2 ) m CH(OH)CO 2 R 1 , —(CH 2 ) m COCO 2 R 1 , —(CH 2 ) m CH═CHCO 2 R 1 , or —(CH 2 ) m O(CH 2 )CO 2 R 1 ; R 1 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, aryl, or CH 2 CO 2 R 1 ; R 1′ is hydrogen or alkyl of 1-6 carbon atoms E is S, SO, SO 2 , O, or NR 1c ; X is hydrogen, halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, CN, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyaralkyl of 6-12 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy; arylalkoxy, nitro, amino, NR 2 R 2a , NR 2 COR 2a , cycloalkylamino of 3-8 carbon atoms, morpholino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, —OCH 2 CO 2 R 2b or —COR 2c ; Y is hydrogen, halogen, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyaralkyl of 6-12 carbon atoms, —OR 3 , SR 3 , NR 3 R 3a , —COR 3b , morpholine or piperidine; R 1a , R 1c , R 2 , R 2a R 3 , R 3a are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, or aryl; R 1b is alkyl of 1-6 carbon atoms or aryl; R 2b is hydrogen, alkyl of 1-6 carbon atoms; R 2c and R 3b are each, independently, alkyl of 1-6 carbon atoms, aryl, or aralkyl of 6-12 carbon atoms; C is hydrogen, halogen or OR 4 ; R 4 is hydrogen, alkyl of 1-6 carbon atoms, —CH(R 5 )W, —C(CH 3 ) 2 CO 2 R 6 , 5-thiazolidine-2,4-dione, —CH(R 7 )(CH 2 ) m CO 2 R 6 , —COR 6 , —PO 3 (R 6 ) 2 , —SO 2 R 6 , —(CH 2 ) p CH(OH)CO 2 R 6 , —(CH 2 ) p COCO 2 R 6 , —(CH 2 ) p CH═CHCO 2 R 6 , or —(CH2) p O(CH 2 ) q CO 2 R 6 ; R 5 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, aryl, —CH 2 (1H-imidazol-4-yl), —CH 2 (3-1H-indolyl), —CH 2 CH 2 (1,3-dioxo-1,3-dihydro-isoindol-2-yl), —CH 2 CH 2 (1-oxo-1,3-dihydro-isoindol-2-yl), —CH 2 (3-pyridyl), —CH 2 CO 2 H, or —(CH 2 ) n G; G is NR 6a R 7a , NR 6a COR 7a , 2 W is CO 2 R 6 , CONH 2 , CONHOH, CN, CONH(CH 2 ) 2 CN, 5-tetrazole, —PO 3 (R 6 ) 2 , —CH 2 OH, —CONR 6b CHR 7b , —CH 2 NR 6b CHR 7b CO 2 R 6 , —CH 2 OCHR 7b CO 2 R 6 —CH 2 Br, or —CONR 6b CHR 7b CO 2 R 6 ; R 6 , R 6a , R 7 , R 7a are each, independently, is hydrogen, alkyl of 1-6 carbon atoms, or aryl; R 6b is hydrogen or —COR 6c ; R 6c is alkyl of 1-6 carbon atoms or aryl; R 7b is hydrogen, alkyl of 1-6 carbon atoms, or hydroxyalkyl of 1-6 carbon atoms; Z 1 and Z 2 are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, cycloalkyl of 3-8 carbon atoms, nitro, amino, —NR 1 R 1a , —NR 1 COR 1a , cycloalkylamino of 3-8 carbon atoms, morpholino, or OR 8 , or Z 1 and Z 2 may be taken together as a diene unit having the formula —CH═CR 9 —CR 10 ═CR 11 —; R 8 is hydrogen, alkyl of 1-6 carbon atoms, or aryl; R 9 , R 10 , and R 11 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aryl, halogen, hydroxy, or alkoxy of 1-6 carbon atoms m is 1 to 4 n is 1 or 2; p is 1 to 4; q is 1 to 4; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

  本发明提供了具有结构式I的化合物： 其中1A是氢、卤素或OH； B和D分别是氢、卤素、CN、1-6个碳原子的烷基、6-12个碳原子的芳基、6-12个碳原子的芳基烷基、1-6个碳原子的羟基烷基、6-12个碳原子的羟基芳基烷基、3-8个碳原子的环烷基、硝基、氨基、—NR1R1a、—NR1COR1a、—NR1CO2R1a、3-8个碳原子的环烷基氨基、吗啉基、呋喃-2-基、呋喃-3-基、噻吩-2-基、噻吩-3-基、—COR1bor OR； R是氢、1-6个碳原子的烷基、—COR1、—（CH2）nCO2R1、—CH（R1a）CO2R1、—SO2R1、—（ ）mCH（OH）CO2R1、—（ ）mCOCO2R1、—（ ）mCH═CHCO2R1或—（ ）mO（ ）CO2R1； R1是氢、1-6个碳原子的烷基、6-12个碳原子的芳基烷基、芳基或 CO2R1； R1'是氢或1-6个碳原子的烷基； E是S、SO、SO2、O或NR1c； X是氢、卤素、1-6个碳原子的烷基、2-7个碳原子的烯基、CN、6-12个碳原子的芳基烷基、1-6个碳原子的羟基烷基、6-12个碳原子的羟基芳基烷基、1-6个碳原子的全氟烷基、1-6个碳原子的烷氧基、芳氧基、芳基烷氧基、硝基、氨基、NR2R2a、NR2COR2a、3-8个碳原子的环烷基氨基、吗啉基、1-6个碳原子的烷基硫醇、芳基硫醇、吡啶基硫醇、2-N，N-二甲基氨基乙基硫醇、—O CO2R2bor—COR2c； Y是氢、卤素、1-6个碳原子的烷基、芳基、6-12个碳原子的芳基烷基、1-6个碳原子的羟基烷基、6-12个碳原子的羟基芳基烷基、—OR3、SR3、NR3R3a、—COR3b、吗啉或哌啶； R1a、R1c、R2、R2a、R3、R3a各自独立地是氢、1-6个碳原子的烷基、6-12个碳原子的芳基烷基或芳基； R1b是1-6个碳原子的烷基或芳基； R2b是氢或1-6个碳原子的烷基； R2c和R3b各自独立地是1-6个碳原子的烷基、芳基或6-12个碳原子的芳基烷基； C是氢、卤素或OR4； R4是氢、1-6个碳原子的烷基、—CH（R5）W、—C（CH3）2CO2R6、5-噻唑烷-2,4-二酮、—CH（R7）（ ）mCO2R6、—COR6、—PO3（R6）2、—SO2R6、—（ ）pCH（OH）CO2R6、—（ ）pCOCO2R6、—（ ）pCH═CHCO2R6或—（ ）pO（ ）qCO2R6； R5是氢、1-6个碳原子的烷基、6-12个碳原子的芳基烷基、芳基、— （1H-咪唑-4-基）、— （3-1H-吲哚基）、— （1,3-二氢-2-氮杂萘-2-基）、— （1-氧代-1,3-二氢-2-氮杂萘-2-基）、— （3-吡啶基）、— CO2H或—（ ）nG； G是NR6aR7a、NR6aCOR7a、2W是CO2R6、CONH2、CONHOH、CN、CONH（ ）2CN、5-四唑、—PO3（R6）2、— OH、—CONR6bCHR7b、— NR6bCHR7bCO2R6、— OCHR7bCO2R6— Br或—CONR6bCHR7bCO2R6； R6、R6a、R7、R7a各自独立地是氢、1-6个碳原子的烷基或芳基； R6b是氢或—COR6c； R6c是1-6个碳原子的烷基或芳基； R7b是氢、1-6个碳原子的烷基或1-6个碳原子的羟基烷基； Z1和Z2各自独立地是氢、卤素、CN、1-6个碳原子的烷基、芳基、6-12个碳原子的芳基烷基、3-8个碳原子的环烷基、硝基、氨基、—NR1R1a、—NR1COR1a、3-8个碳原子的环烷基氨基、吗啉基或OR8，或Z1和Z2可以作为具有式—CH═CR9—CR10═CR11—的二烯单元一起取代； R8是氢、1-6个碳原子的烷基或芳基； R9、R10和R11各自独立地是氢、1-6个碳原子的烷基、芳基、卤素、羟基或1-6个碳原子的烷氧基； m为1至4； n为1或2； p为1至4； q为1至4； 或其药学上可接受的盐，其用于治疗与胰岛素抵抗或高血糖相关的代谢紊乱。
• NOVEL BICYCLIC NITROGEN CONTAINING HETEROARYL TGR5 RECEPTOR MODULATORS
  申请人：Robl Jeffrey A.

  公开号：US20140080788A1

  公开（公告）日：2014-03-20

  Novel compounds of Formula I:or an enantiomer, diastereomer, tautomer, prodrug or salt thereof, wherein m, Q, T, U, V, ring A, X, Y, R 3 , R 4 , R 4a , R 5a , R 5b , R 5c , R 5d , R 5e , R 6a , R 6b , and R 6c are defined herein, are provided which are TGR5 G protein-coupled receptor modulators. TGR5 G protein-coupled receptor modulators are useful in treating, preventing, or slowing the progression of diseases requiring TGR5 G protein-coupled receptor modulator therapy. Thus, the disclosure also concerns compositions comprising these novel compounds and methods of treating diseases or conditions related to the activity of the TGR5 G protein-coupled receptor by using any of these novel compounds or a composition comprising any of such novel compounds.

  本发明提供了一种公式I的新化合物：或其对映异构体、顺反异构体、互变异构体、前药或其盐，其中m、Q、T、U、V、环A、X、Y、R3、R4、R4a、R5a、R5b、R5c、R5d、R5e、R6a、R6b和R6c的定义如本文所述，这些化合物是TGR5 G蛋白偶联受体调节剂。 TGR5 G蛋白偶联受体调节剂在治疗、预防或减缓需要TGR5 G蛋白偶联受体调节剂治疗的疾病方面具有用途。因此，本公开还涉及包含这些新化合物的组合物以及使用任何这些新化合物或包含任何这些新化合物的组合物来治疗与TGR5 G蛋白偶联受体活性相关的疾病或病症的方法。
• Direct B-Alkyl Suzuki-Miyaura Cross-Coupling of Trialkyl- boranes with Aryl Bromides in the Presence of Unmasked Acidic or Basic Functions and Base-Labile Protections under Mild Non-Aqueous Conditions
  作者：Bing Wang、Hui-Xia Sun、Zhi-Hua Sun、Guo-Qiang Lin

  DOI：10.1002/adsc.200800630

  日期：2009.2

  Abstractmagnified imageAn efficient and chemoselective palladium‐catalyzed direct B‐alkyl Suzuki–Miyaura cross‐coupling of trialkylboranes with diversely functionalized aryl bromides is described. A wide variety of unmasked acidic or basic functions are tolerated. The mild non‐aqueous conditions are compatible with aldehydes, ketones, nitriles, chloro substitution as well as base‐labile phenolic Piv and TBS protecting groups. The anhydrous conditions were found to be advantageous for aryl bromide substrates. A potent CEPT inhibitor was efficiently synthesised using this protocol.
• B-Alkyl Suzuki–Miyaura cross-coupling of tri-n-alkylboranes with arylbromides bearing acidic functions under mild non-aqueous conditions
  作者：Hui-Xia Sun、Zhi-Hua Sun、Bing Wang

  DOI：10.1016/j.tetlet.2009.01.090

  日期：2009.4

  An efficient and chemoselective Pd-catalyzed B-alkyl Suzuki-Miyaura cross-coupling of tri-n-alkylboranes with arylbromides possessing acidic functions is described. This protocol features the relatively weak base CS2CO3 and mild non-aqueous conditions. Aldehydes, ketones, nitriles, and chloro substitution are all tolerated. (C) 2009 Elsevier Ltd. All rights reserved.