4-(4-methoxy-3-methylphenyl)butyric acid | 33446-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxy-3-methylphenyl)butyric acid
• 英文别名: 4-(3'-methyl-4'-methoxyphenyl)butanoic acid；4-(4-methoxy-3-methylphenyl)butanoic acid；1-(4-methoxy-3-methylphenyl)butyric acid；4-(4-methoxy-3-methyl-phenyl)-butyric acid；4-(4-Methoxy-3-methyl-phenyl)-buttersaeure
• CAS: 33446-15-0
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD03140576
• 分子量: 208.257
• InChiKey: CWNPAVGNPUYSNX-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  210 °C(Press: 14 Torr)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  4-(4-methoxy-3-methylphenyl)butyric acid 在 sodium tetrahydroborate 、 甲烷磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 1,2,3,4-tetrahydro-6-methyl-7-methoxy-1-naphthalenol
  参考文献：
  名称：

  Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists

  摘要：

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.

  DOI：

  10.1021/jm00129a029
• 作为产物：
  描述：

  2-甲基苯甲醚 在 盐酸 、 三氯化铝 、 汞 、 锌 作用下， 以 水 、 硝基苯 、 甲苯 为溶剂， 反应 49.0h， 生成 4-(4-methoxy-3-methylphenyl)butyric acid
  参考文献：
  名称：

  xxx, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 11, p. 822 - 825

  摘要：

  DOI：

文献信息

• Amines substituted with a dihydronaphthalenyl, chromenyl, or thiochromenyl group, an aryl or heteroaryl group and an alkyl group, having retinoid-like biological activity
  申请人：——

  公开号：US20030166932A1

  公开（公告）日：2003-09-04

  Compounds of the formula 1 where the symbols are as defined in the specification, have retinoid agonist, antagonist or negative hormone-like biological activity.

  式中符号如规范中定义，具有视黄醇激动剂、拮抗剂或负激素样生物活性。
• A Novel Type of Retinoic Acid Receptor Antagonist: Synthesis and Structure-Activity Relationships of Heterocyclic Ring-Containing Benzoic Acid Derivatives
  作者：Hiroyuki Yoshimura、Mitsuo Nagai、Shigeki Hibi、Kouichi Kikuchi、Shinya Abe、Takayuki Hida、Seiko Higashi、Ieharu Hishinuma、Takashi Yamanaka

  DOI：10.1021/jm00016a020

  日期：1995.8

  A new series of heterocyclic ring-containing benzoic acids was prepared, and the binding affinity and antagonism of its members against all-trans-retinoic acid were evaluated by in vitro assay systems using human promyelocytic leukemia (HL-60) cells. Structure-activity relationships indicated that both an N-substituted pyrrole or pyrazole (1-position) and a hydrophobic region, with these linked by

  制备了一系列新的含杂环苯甲酸，并通过体外检测系统使用人类早幼粒细胞白血病（HL-60）细胞评估了其成员对全反式维甲酸的结合亲和力和拮抗作用。结构活性关系表明，N-取代的吡咯或吡唑（1-位）和疏水区（通过环系统连接）对于有效拮抗都是必不可少的。在所评估的化合物中，最佳拮抗作用是通过4- [4,5,7,8,9,10-六氢-7,7,10，-10-四甲基-1-（3-吡啶基甲基）蒽[1,2 -b]吡咯-3-基]苯甲酸（31），4- [4,5,7,8,9,10-六氢-7,7,10,10-四甲基-1-（3-吡啶基甲基）- 5-硫杂蒽[1,2-b]吡咯-3-基]苯甲酸（40）和4- [4,5,7,8,9,10-六氢-7,7,10,10-四甲基- 1-（3-吡啶基甲基）蒽[2，
• Friedel-Crafts Acylation Reactions Using Esters
  作者：Subhash P. Chavan、Sumanta Garai、Achintya Kumar Dutta、Sourav Pal

  DOI：10.1002/ejoc.201201181

  日期：2012.12

  Intermolecular and intramolecular Friedel–Crafts acylation reactions of various aliphatic and aromatic esters at room temperature with the use of very simple reagents and activating groups in are described. The products were obtained in good yield (60–85 %). The detailed mechanistic pathway was studied by DFT calculations and supported by experimental evidence.

  描述了使用非常简单的试剂和活化基团在室温下各种脂肪族和芳香族酯的分子间和分子内 Friedel-Crafts 酰化反应。产品以良好的收率（60-85%）获得。通过 DFT 计算研究了详细的机械路径，并得到了实验证据的支持。
• Production of adenine nucleotide translocator (ANT), novel ANT ligands and screening assays therefor
  申请人：——

  公开号：US20010044144A1

  公开（公告）日：2001-11-22

  Compositions and methods are provided for producing adenine nucleotide translocator (ANT) polypeptides and fusion proteins, including the production and use of recombinant expression constructs having a regulated promoter. ANT ligands and compositions and methods for identifying ANT ligands, agents that bind ANT and agents that interact with ANT are also disclosed.

  本发明提供了用于制备腺嘌呤核苷酸转运蛋白（ANT）多肽和融合蛋白的组合物和方法，包括具有调节启动子的重组表达载体的制备和使用。本发明还公开了ANT配体和用于识别ANT配体、结合ANT的药剂和与ANT相互作用的药剂的组合物和方法。
• A diastereoselective total synthesis of the sesquiterpene (±)-mutisianthol
  作者：Helena M.C Ferraz、Andrea M Aguilar、Luiz F Silva

  DOI：10.1016/s0040-4020(03)00974-8

  日期：2003.7

  The total synthesis of the phenolic sesquiterpene mutisianthol has been accomplished in 12 steps from the readily available 2-methylanisole. The required trans-1,3-disubstituted indan intermediate was obtained through a diastereoselective thallium(III) mediated ring contraction of a 1-methyl-1,2-dihydronaphthalene derivative.

  从容易获得的2-甲基苯甲醚以十二个步骤完成了酚倍半萜烯泛醇的全合成。所需的反式-1,3-二取代的茚满中间体是通过非对映选择性的（（III）介导的1-甲基-1，2-二氢萘衍生物的环收缩而获得的。