2-(4'-methoxyphenoxy)propanoic acid chloride | 92818-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4'-methoxyphenoxy)propanoic acid chloride
• 英文别名: 2-(4-methoxyphenoxy)propionyl chloride；2-(4-methoxyphenoxy)propanoyl chloride
• CAS: 92818-05-8
• 化学式: C₁₀H₁₁ClO₃
• mdl: MFCD03421596
• 分子量: 214.649
• InChiKey: IOMGKYYTJICTNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-methoxyphenoxy)propanoic acid chloride 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 4'-methyl-2',6'-di-tert-butylphenyl (2RS,3RS)-2,4-dimethyl-3-hydroxy-2-(4"-methoxyphenoxy)hexanoate
  参考文献：
  名称：

  非循环立体选择。23. 乳醛烯醇化物当量

  摘要：

  Etudie lastereochimie de l'addition d'enolates d'esters d'acide O-alkyllactique aux aldehydes

  DOI：

  10.1021/ja00338a027
• 作为产物：
  描述：

  lactisole 在 氯化亚砜 、 磷酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(4'-methoxyphenoxy)propanoic acid chloride
  参考文献：
  名称：

  非循环立体选择。23. 乳醛烯醇化物当量

  摘要：

  Etudie lastereochimie de l'addition d'enolates d'esters d'acide O-alkyllactique aux aldehydes

  DOI：

  10.1021/ja00338a027

文献信息

• Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature
  作者：Loorthuraja Rasu、Jeremy M. John、Elanna Stephenson、Riley Endean、Suneth Kalapugama、Roxanne Clément、Steven H. Bergens

  DOI：10.1021/jacs.6b12254

  日期：2017.3.1

  High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.

  高通量筛选和实验室规模优化相结合，开发了催化系统 trans-RuCl2((S,S)-skewphos)((R,R)-dpen)、2-PrONa 和 2-PrOH。该系统在室温和 4 个大气压的 H2 压力下氢化功能化的 α-苯氧基和相关酰胺，通过动态动力学拆分以高达 99% 的产率和大于 99% 的对映体过量得到手性醇。
• Synthesis and Herbicidal Activity of 2-Aroxy-propanamides Containing Pyrimidine and 1,3,4-Thiadiazole Rings
  作者：Man-Yun Liu、De-Qing Shi

  DOI：10.1002/jhet.1853

  日期：2014.3

  4]thiadiazol‐2‐yl}2‐aroxy‐propanamides were designed and synthesized by the multistep reactions. 2‐(4,6‐Dimethoxy‐pyrimidin‐2‐yloxy)‐benzaldehyde (1) reacted with aminothiourea to yield 2, which undergoes ring closure to give 5‐[2‐(4,6‐dimethoxy‐pyrimidin‐2‐yloxy)‐phenyl]‐[1,3,4]thiadiazol‐2‐amine (3) in the presence of ferric chloride in refluxing ethanol. 3 reacted with 2‐aroxy‐propionyl chlorides to give

  设计并设计了一系列新颖的N- 5- [2-（4,6-二甲氧基-嘧啶-2-基氧基）苯基]-[1,3,4]噻二唑-2-基} 2-芳氧基丙酰胺并通过多步反应合成。2-（4,6-二甲氧基-嘧啶-2-基氧基）苯甲醛（1）与氨基硫脲反应生成2，然后进行闭环反应生成5- [2-（4,6-二甲氧基-嘧啶--2-基氧基） ）-苯基]-[1,3,4]噻二唑-2-胺（3）在氯化铁存在下于回流的乙醇中。3与2-芳氧基丙酰氯反应生成目标化合物4a，4b，4c，4d，4e，4f，4g，4h，4i处于中等至良好的产量。通过IR，1 H-NMR，EIMS和元素分析确认了它们的结构。初步的生物测定结果表明，其中一些对甘蓝型油菜表现出中度至良好的选择性除草活性。浓度为100 mg / L。但是，这些化合物在所测试的浓度下不具有对against棘手E的抑制活性。
• PRECURSOR COMPOUNDS OF SWEET TASTE RECEPTOR ANTAGONISTS FOR THE PREVENTION OR TREATMENT OF DISEASE
  申请人：Ley Jakob Peter

  公开号：US20110045069A1

  公开（公告）日：2011-02-24

  A description is given of precursor compounds of sweet taste receptor antagonists for the prevention or treatment of disease, in particular for the prevention or treatment of Type 2 diabetes. A description is also given of uses of these precursor compounds and edible compositions, preparations for nutrition or pleasure or semi-finished products and pharmaceutical preparations, containing such precursor compounds.

  描述了甜味受体拮抗剂的前体化合物，用于预防或治疗疾病，特别是用于预防或治疗2型糖尿病。还描述了这些前体化合物的用途，以及包含这些前体化合物的食用组合物、营养或愉悦制剂、半成品和含有这些前体化合物的药物制剂。
• Mutual Kinetic Resolution of Racemic 3,4-Dihydro-3-methyl-2<i>H</i> -[1,4]benzoxazines with Acyl Chlorides of Racemic <i>O</i> -Phenyllactic Acids and DFT Modelling of Transition States
  作者：Marina A. Korolyova、Sergey A. Vakarov、Dmitry N. Kozhevnikov、Dmitry A. Gruzdev、Galina L. Levit、Victor P. Krasnov

  DOI：10.1002/ejoc.201800656

  日期：2018.9.9

  The acylative kinetic resolution of 3,4‐dihydro‐3‐methyl‐2H‐[1,4]benzoxazines with racemic 2‐aryloxypropionyl chlorides has been studied experimentally and the geometries of the diastereoisomeric transition states determined by DFT calculations. It has been found that quantum chemical calculations describe well the quantitative dependence of the acylation selectivity on the reagents' structures.

  实验研究了3,4-二氢-3-甲基-2 H- [1,4]苯并恶嗪与外消旋2-芳氧基丙酰氯的酰基动力学拆分，并通过DFT计算确定了非对映异构过渡态的几何形状。已经发现，量子化学计算很好地描述了酰化选择性对试剂结构的定量依赖性。
• Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
  作者：Alessia Carocci、Alessia Catalano、Angelo Lovece、Giovanni Lentini、Andrea Duranti、Valeria Lucini、Marilou Pannacci、Francesco Scaglione、Carlo Franchini

  DOI：10.1016/j.bmc.2010.06.100

  日期：2010.9

  A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists. (C) 2010 Elsevier Ltd. All rights reserved.