2-(3-甲氧基苯基)丙酸 | 3146-60-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 2-(3-甲氧基苯基)丙酸
• 英文名称: 2-(3-methoxyphenyl)propanoic acid
• 英文别名: 2-(3-methoxyphenyl)propionic acid；(+/-)-2-<3-Methoxy-phenyl>-propionsaeure
• CAS: 3146-60-9
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD11036874
• 分子量: 180.203
• InChiKey: SJGKYVCZSNGHPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  2-(3-甲氧基苯基)丙酸 在 sodium hydroxide 、 氯化亚砜 、 乙酸酐 、 三乙胺 作用下， 反应 0.5h， 生成 3-[2-[1-(3-methoxyphenyl)ethyl]-5-oxo-4-propan-2-yl-1,3-oxazol-2-yl]propanenitrile
  参考文献：
  名称：

  McKay, Roslyn; Proctor, George R., Journal of Chemical Research - Part S, 1996, # 2, p. 98 - 99

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3-甲氧基苯基)丙酸乙酯 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以91%的产率得到2-(3-甲氧基苯基)丙酸
  参考文献：
  名称：

  A Versatile Synthesis of O-Desmethylangolensin Analogues from Methoxy-Substituted Benzoic Acids

  摘要：

  该研究描述了从甲氧基取代的苯甲酸合成 O-去甲基郎格列新（O-DMA）类似物的过程。甲氧基取代的苯甲酸用 2 等量的乙锂处理后得到甲氧基苯丙酮，随后在原甲酸三乙酯中使用 $Pb(OAc)_4/HClO_4$ 通过甲氧基苯基基团的 1,2 重排转化为 2-(甲氧基苯基)丙酸乙酯。用 KOH 进行水解后，2-(甲氧基苯基)丙酸与碳酸二-2-吡啶反应，得到 2-(甲氧基苯基)丙酸 2-吡啶酯，再与甲氧基取代的苯基溴化镁酰化，得到甲氧基-$\{alpha}$-甲基去氧苯甲酸酯。使用三溴化硼对这些化合物的甲氧基进行选择性或完全脱甲基化，可以高产率得到多种 O-DMA 类似物。

  DOI：

  10.5012/jkcs.2014.58.6.569

文献信息

• [EN] SUBSTITUTED BENZAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS DE BENZAMIDE SUBSTITUÉS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011076678A1

  公开（公告）日：2011-06-30

  The invention relates to compounds of formula I wherein R is hydrogen or lower alkyl; R1 is -(CH2)n-(O)o-heterocycloalkyl or -C(O)-heterocycloalkyl, wherein the heterocycloalkyl group is optionally substituted by lower alkyl, hydroxy, halogen or by -(CH2)p-aryl; n is 0, 1 or 2; o is 0 or 1; p is 0, 1 or 2; R2 is CF3, cycloalkyl, optionally substituted by lower alkoxy or halogen, or is indan-2-yl, or is heterocycloalkyl, optionally substituted by heteroaryl, or is aryl or heteroaryl, wherein the aromatic rings are optionally substituted by one or two substituents, selected from lower alkyl, halogen, heteroaryl, hydroxy, CF3, OCF3, OCH2CF3, OCH2-cycloalkyl, OCH2C(CH2OH)(CH2C1)(CH3), S-lower alkyl, lower alkoxy, CH2-lower alkoxy, lower alkinyl or cyano, or by-C(O)-phenyl, -O-phenyl, -O- CH2-phenyl, phenyl or -CH2-phenyl, and wherein the phenyl rings may optionally be substituted by halogen, -C(O)-lower alkyl, -C(O)OH or -C(O)O-lower alkyl, or the aromatic rings are optionally substituted by heterocycloalkyl, OCH2-oxetan-3-yl or O-tetrahydropyran-4-yl, optionally substituted by lower alkyl; X is a bond, -NR'-, -CH2NH-, -CHR''-, -(CHR'')q-O-, -O-(CHR'')q- or -(CH2)2-; Y is a bond or -CH2- R' is hydrogen or lower alkyl, R'' is hydrogen, lower alkyl, CF3, lower alkoxy, q is 0, 1, 2 or 3; or to a pharmaceutically suitable acid addition salt thereof. It has now been found that the compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinsons disease, neurodegenerative disorders such as Alzheimers disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  该发明涉及以下式I的化合物，其中R是氢或较低的烷基；R1是-(CH2)n-(O)o-杂环烷基或-C(O)-杂环烷基，其中杂环烷基基团可选择地被较低的烷基，羟基，卤素或-( )p-芳基取代；n为0、1或2；o为0或1；p为0、1或2；R2为CF3，环烷基，可选择地被较低的烷氧基或卤素取代，或为茚-2-基，或为杂环烷基，可选择地被杂芳基取代，或为芳基或杂芳基，其中芳香环可选择地被来自较低的烷基，卤素，杂芳基，羟基， ，O ，O ，O -环烷基，O C( OH)( C1)(CH3)，S-较低的烷基，较低的烷氧基， -较低的烷氧基，较低的炔基或氰基，或-C(O)-苯基，-O-苯基，-O- -苯基，苯基或- -苯基选择的一个或两个取代基取代，其中苯环可选择地被卤素，-C(O)-较低的烷基，-C(O)OH或-C(O)O-较低的烷基取代，或芳香环可选择地被杂环烷基，O -氧杂环戊烷-3-基或O-四氢吡喃-4-基，可选择地被较低的烷基取代；X为键，-NR'-，- NH-，-CHR''-，-(CHR'')q-O-，-O-(CHR'')q-或-( )2-；Y为键或- -；R'为氢或较低的烷基，R''为氢，较低的烷基， ，较低的烷氧基，q为0、1、2或3；或其药学上适宜的酸盐。现已发现，该式I的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对于TAAR1。这些化合物可用于治疗抑郁症，焦虑症，躁郁症，注意力缺陷多动障碍（ADHD），与压力有关的疾病，如精神分裂症，帕金森病等神经疾病，阿尔茨海默病等神经退行性疾病，癫痫，偏头痛，高血压，物质滥用和代谢性疾病，如进食障碍，糖尿病，糖尿病并发症，肥胖症，血脂异常，能量消耗和吸收异常，体温稳态异常，睡眠和昼夜节律异常，以及心血管疾病。
• 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。
• SUBSTITUTED BENZAMIDES
  申请人：Groebke Zbinden Katrin

  公开号：US20110152245A1

  公开（公告）日：2011-06-23

  The invention relates to compounds of formula wherein R, R 1 , R 2 , X, and Y are as defined herein and to a pharmaceutically suitable acid addition salt thereof. Compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds can be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  该发明涉及以下式的化合物 其中R、R1、R2、X和Y如本文所定义，并且其药学上适宜的酸盐。 式I的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑障碍、双相情感障碍、注意缺陷多动障碍（ADHD）、与压力有关的障碍、如精神分裂症的精神障碍、如帕金森病的神经疾病、如阿尔茨海默病的神经退行性疾病、癫痫、偏头痛、高血压、物质滥用和代谢性障碍，如进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍，以及心血管疾病。
• BENZOAZEPIN-OXY-ACETIC ACID DERIVATIVES AS PPAR-DELTA AGONISTS USED FOR THE INCREASE OF HDL-C, LOWER LDL-C AND LOWER CHOLESTEROL
  申请人：Kuo Gee-Hong

  公开号：US20070244094A1

  公开（公告）日：2007-10-18

  The invention is directed to compounds of Formula (I) useful as PPAR agonists. Pharmaceutical compositions and methods of treating one or more conditions including, but not limited to, diabetes, nephropathy, neuropathy, retinopathy, polycystic ovary syndrome, hypertension, ischemia, stroke, irritable bowel disorder, inflammation, cataract, cardiovascular diseases, Metabolic X Syndrome, hyper-LDL-cholesterolemia, dyslipidemia (including hypertriglyceridemia, hypercholesterolemia, mixed hyperlipidemia, and hypo-HDL-cholesterolemia), atherosclerosis, obesity, and other disorders related to lipid metabolism and energy homeostasis complications thereof, using compounds of the invention are also described.

  该发明涉及一种化合物，其化学式为（I），可用作PPAR激动剂。还描述了使用该发明的化合物治疗糖尿病、肾病、神经病、视网膜病变、多囊卵巢综合征、高血压、缺血、中风、肠易激综合征、炎症、白内障、心血管疾病、代谢X综合征、高LDL胆固醇血症、血脂异常（包括高甘油三酯血症、高胆固醇血症、混合性高脂血症和低HDL胆固醇血症）、动脉粥样硬化、肥胖以及其他与脂质代谢和能量稳态并发症相关的疾病的药物组合物和治疗方法。
• [EN] N-ARYL AND N-HETEROARYL PIPERIDINE DERIVATIVES AS LIVER X RECEPTOR β AGONISTS, COMPOSITIONS, AND THEIR USE<br/>[FR] DÉRIVÉS DE N-ARYLE ET DE N-HÉTÉROARYLE PIPÉRIDINE EN TANT QU'AGONISTES DES RÉCEPTEURS HÉPATIQUES X, COMPOSITIONS ET LEUR UTILISATION
  申请人：MERCK SHARP & DOHME

  公开号：WO2018068297A1

  公开（公告）日：2018-04-19

  Provided herein are certain substituted N-aryl and N-heteroaryl piperidine compounds of the formula (I) and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, L, R4, L1, Q, R5 and R 6 are as defined. The said novel compounds, and pharmaceutically acceptable compositions comprising a compound thereof, may be useful as Liver X-β receptor(LXRβ) agonists, and may be useful for treating or preventing pathologies related thereto. Such pathologies include, but are not limited to, inflammatory disease and diseases characterized by defects in cholesterol and lipid metabolism, such as Alzheimer's disease.

  提供的是某些取代的N-芳基和N-杂芳基哌啶化合物，其化学式为(I)以及药用可接受的盐，其中R1、R2、R3、L、R4、L1、Q、R5和R6定义如所述。所述新颖化合物，以及包含其化合物的药用可接受组合物，可能用作肝X-β受体(LXRβ)激动剂，并可用于治疗或预防与之相关的病理学。这类病理学包括但不限于炎症性疾病和以胆固醇和脂质代谢缺陷为特征的疾病，例如阿尔茨海默病。