2-acetamido-2-(4-methoxyphenyl) acetic acid | 52771-14-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-2-(4-methoxyphenyl) acetic acid
• 英文别名: N-acetyl-α-(4-methoxyphenyl)glycine；(Acetylamino)(4-methoxyphenyl)acetic acid；2-acetamido-2-(4-methoxyphenyl)acetic acid
• CAS: 52771-14-9
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: KAGSUJOTNBINKR-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  479.4±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-(4-methoxyphenyl) acetic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(4-甲氧基苯基)-2-甲基-1,3-恶唑-5(4H)-酮
  参考文献：
  名称：

  Diastereochemical Diversity of Imidazoline Scaffolds via Substrate Controlled TMSCl Mediated Cycloaddition of Azlactones

  摘要：

  We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.

  DOI：

  10.1021/ol052118w
• 作为产物：
  描述：

  2-acetamido-2-(4'-methoxyphenyl)acetate d'ethyle 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以81%的产率得到2-acetamido-2-(4-methoxyphenyl) acetic acid
  参考文献：
  名称：

  Diastereochemical Diversity of Imidazoline Scaffolds via Substrate Controlled TMSCl Mediated Cycloaddition of Azlactones

  摘要：

  We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.

  DOI：

  10.1021/ol052118w

文献信息

• Merging Visible-Light Photoredox and Chiral Phosphate Catalysis for Asymmetric Friedel–Crafts Reaction with in Situ Generation of <i>N</i>-Acyl Imines
  作者：Meng-Lan Shen、Yang Shen、Pu-Sheng Wang

  DOI：10.1021/acs.orglett.9b00442

  日期：2019.5.3

  In the presence of visible-light photoredox and chiral phosphate catalysts, a novel asymmetric Friedel–Crafts reaction of indoles and readily accessible α-amino acid derived redox-active esters is established to afford enantioenriched 1-indolyl-1-alkylamine derivatives in moderate to high yields and with high levels of enantioselectivities. This method not only shows a mild and efficient alternative

  在可见光的光氧化还原和手性磷酸酯催化剂的存在下，建立了吲哚和容易获得的α-氨基酸衍生的氧化还原活性酯的新型不对称Friedel-Crafts反应，以提供中等至中等浓度的对映体富集的1-吲哚基-1-烷基胺衍生物。高收率和高对映选择性。该方法不仅显示了N-酰基亚胺的原位生成的温和而有效的替代方法，而且表明了用于不对称光氧化还原催化的多催化剂体系的可行性。
• [EN] BICYCLIC HETEROCYCLIC DERIVATIVES AS BROMODOMAIN INHIBITORS<br/>[FR] DÉRIVÉS BICYCLIQUES HÉTÉROCYCLIQUES COMME INHIBITEURS DE BROMODOMAINES
  申请人：AURIGENE DISCOVERY TECH LTD

  公开号：WO2015104653A1

  公开（公告）日：2015-07-16

  The present invention provides bicyclic heterocyclic derivatives of formula (I), which may be therapeutically useful, more particularly as bromodomain inhibitors; (I), in which R1, R2, R3, R4, L1, L2, Cy1, Cy2, X, n and dotted line are have the same meaning given in the specification, and pharmaceutically acceptable salts or pharmaceutically acceptable stereoisomers thereof that are useful in the treatment and prevention of diseases or disorder, in particular their use in diseases or disorder associated as bromodomain inhibitors. The present invention also provides preparation of the compounds and pharmaceutical formulations comprising at least one of bicyclic heterocyclic derivatives of formula (I), together with a pharmaceutically acceptable carrier, diluent or excipient therefor.

  本发明提供了公式（I）的双环杂环衍生物，可能在治疗上有用，更具体地作为溴结构域抑制剂；其中R1、R2、R3、R4、L1、L2、Cy1、Cy2、X、n和虚线在说明书中具有相同的含义，并且其药学上可接受的盐或药学上可接受的立体异构体在治疗和预防疾病或紊乱方面有用，特别是它们在作为溴结构域抑制剂相关的疾病或紊乱中的使用。本发明还提供了该类化合物的制备以及包含至少一种公式（I）的双环杂环衍生物的药物配方，连同药学上可接受的载体、稀释剂或赋形剂。
• BICYCLIC HETEROCYCLIC DERIVATIVES AS BROMODOMAIN INHIBITORS
  申请人：ORION CORPORATION

  公开号：US20160368906A1

  公开（公告）日：2016-12-22

  The present disclosure provides bicyclic heterocyclic derivatives of formula (I), which may be therapeutically useful, more particularly as bromodomain inhibitors; (I), in which R 1 , R 2 , R 3 , R 4 , L 1 , L 2 , Cy 1 , Cy 2 , X, n, and dotted line have the same meaning given in the specification, and pharmaceutically acceptable salts or pharmaceutically acceptable stereoisomers thereof that are useful in the treatment and prevention of diseases or disorders, in particular their use in diseases or disorders associated as bromodomain inhibitors. The present disclosure also provides preparation of compounds and pharmaceutical formulations comprising at least one of bicyclic heterocyclic derivatives of formula (I), together with a pharmaceutically acceptable carrier, diluent, or excipient.

  本公开提供了公式（I）的双环杂环衍生物，可能在治疗上有用，更具体地作为溴结构域抑制剂；（I）中，R1、R2、R3、R4、L1、L2、Cy1、Cy2、X、n和虚线具有规范中给定的相同含义，以及其在治疗和预防疾病或疾病中有用，特别是在与溴结构域抑制剂相关的疾病或疾病中的使用。本公开还提供了制备化合物和包括至少一种公式（I）的双环杂环衍生物的药物配方，以及药学上可接受的载体、稀释剂或赋形剂。
• Efficient Ligand-Free, Palladium-Catalyzed Amidocarbonylation in Ionic Liquids: Facile Synthesis of <i>N</i>-Acyl-<font>α</font>-arylglycines
  作者：Qing-Lu Zhao、Min Yang、Lai-Lai Wang

  DOI：10.1080/00397910802369588

  日期：2008.11.13

  Abstract A ligand-free, palladium-catalyzed amidocarbonylation reaction of aromatic aldehyde, acetamide, and CO in ionic liquids [C4mim]PF6, [C6mim]PF6, [C8mim]PF6, and [C6mim]BF4 as solvents is developed. The yields decreased in the order [C6mim]PF6 > [C8mim]PF6 > [C4mim]PF6 > [C6mim]BF4, and substrate concentration affected the catalytic activity of amidocarbonylation. The excellent yield with up

  摘要 开发了一种无配体、钯催化的芳香醛、乙酰胺和 CO 在离子液体 [C4mim]PF6、[C6mim]PF6、[C8mim]PF6 和 [C6mim]BF4 溶剂中的酰胺羰基化反应。产率依次为[C6mim]PF6>[C8mim]PF6>[C4mim]PF6>[C6mim]BF4，底物浓度影响酰胺羰基化的催化活性。在 80 °C 下使用 15 mol% LiBr·H2O 和 6 mol% H2SO4 获得了高达 98% 的苯甲醛酰胺羰基化的优异收率。该反应可以顺利进行，产生了几种功能化的邻、间和对位取代的 N-酰基-α-苯基甘氨酸，收率中等至良好，并且作为底物的邻甲苯醛和间甲苯醛首次被酰胺羰基化。 [C6mim]PF6。观察到产物产率对芳香醛的取代基位置和电子效应的显着依赖性。无配体的合成方法和产品的方便分离突出了这种新开发方法的多功能性。
• Efficient synthesis of N-acyl-α-amino acids via polymer incarcerated palladium-catalyzed amidocarbonylation
  作者：Ryo Akiyama、Takahiro Sagae、Masaharu Sugiura、Shū Kobayashi

  DOI：10.1016/j.jorganchem.2004.07.017

  日期：2004.11

  A novel polymer incarcerated Pd catalyst (PI Pd 7c) was synthesized from amide-containing polymer 6b, and this catalyst was shown to be effective in amidocarbonylation, which is a versatile one-pot method for the preparation of N-acyl-α-amino acids. The reactions proceeded smoothly with a wide variety of substrates, and no leaching of the Pd metal to the reaction mixture was detected.

  由含酰胺的聚合物6b合成了一种新型的聚合物嵌载Pd催化剂（PI Pd 7c），该催化剂对酰胺羰基化反应有效，是一种通用的一锅法制备N-酰基-α-氨基的方法。酸。反应在各种底物上均能顺利进行，并且未检测到Pd金属向反应混合物中的浸出。