N-(2-methoxybenzyl)acetamide | 63452-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(2-methoxybenzyl)acetamide
• 英文别名: N-[(2-methoxyphenyl)methyl]acetamide
• CAS: 63452-53-9
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD00996307
• 分子量: 179.219
• InChiKey: UKDWIXWBWBKHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-methoxybenzyl)acetamide 在 三(三氟乙酸)碘 、 铜 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 为溶剂， 生成 ethyl (2S)-2-acetamido-3-[4-[3-(acetamidomethyl)-4-methoxyphenoxy]-3,5-diiodophenyl]propanoate
  参考文献：
  名称：

  Thyroid hormone analogs. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart

  摘要：

  Twenty-nine novel 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by a new route involving manipulation of a 3'-formyl intermediate. In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines. Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accommodate a phenyl or cyclohexyl group. Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the adjacent 4'-hydroxyl. The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar. However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences. A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar refractivity) is included in the analysis. These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

  DOI：

  10.1021/jm00396a008
• 作为产物：
  描述：

  邻甲氧基苄胺 在 乙酸酐 作用下， 以69.9%的产率得到N-(2-methoxybenzyl)acetamide
  参考文献：
  名称：

  [EN] INTEGRIN ANTAGONIST CONJUGATES FOR TARGETED DELIVERY TO CELLS EXPRESSING ALPHA-V-BETA-3
  [FR] CONJUGUÉS D'ANTAGONISTE DE L'INTÉGRINE POUR UNE ADMINISTRATION CIBLÉE À DES CELLULES EXPRIMANT L'ALPHA-V-BÊTA-3

  摘要：

  本发明涉及如下公式(I)的化合物：其中R1、R2和n在详细描述和权利要求中定义。特别是，本发明涉及用于制造和输送与alpha-V-beta-3整合素拮抗剂连接的共轭部分，如小分子、肽、核酸、荧光部分和聚合物，以针对表达alpha-V-beta-3的细胞的公式(I)的化合物。

  公开号：

  WO2013110578A1

文献信息

• Environmentally benign decarboxylative <i>N</i>-, <i>O</i>-, and <i>S</i>-acetylations and acylations
  作者：Santanu Ghosh、Anisha Purkait、Chandan K. Jana

  DOI：10.1039/d0gc03731a

  日期：——

  An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically

  已经报道了用于多种底物（胺，醇，酚，硫醇和）的乙酰化和酰化的操作简单且通用的方法。Meldrum的酸及其衍生物已被用作空气稳定，不挥发，具有成本效益且易于处理的乙酰化/酰化剂。易于分离的副产物（CO 2和丙酮）可分离分析纯的乙酰化产物，而无需进行后处理和任何色谱分离。
• Iridium-Catalyzed Benzylamine C–H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group
  作者：Xiao Yang、Rui Sun、Chunchun Zhang、Xueli Zheng、Maolin Yuan、Haiyan Fu、Ruixiang Li、Hua Chen

  DOI：10.1021/acs.orglett.8b04005

  日期：2019.2.15

  The first iridium-catalyzed oxidative alkeynylation of benzylamines with acrylates enabled by a new directing group pentafluorobenzoyl has been developed. The reaction proceeded efficiently in the presence of silver acetate as oxidant and chlorobenzene as solvent. A good range of benzylamines could be selectively monoalkenylated without interfering with further aza-Michael addition. The kinetic isotope

  已经开发出了由新的指向性基团五氟苯甲酰基实现的，首个铱催化的苄胺与丙烯酸酯的氧化炔基化反应。在乙酸银作为氧化剂和氯苯作为溶剂的存在下，反应有效地进行。大量的苄胺可以被选择性地单烯基化而不干扰进一步的氮杂-迈克尔加成。动力学同位素效应实验表明，CH活化不是限速步骤。此外，分离并确定了五元的iridacycle物种，并将其确定为可能的关键中间体。
• Rhodium(III)-Catalyzed Oxidative C–H/C–H Cross-Coupling of Heteroarenes and Masked Benzylamines
  作者：Jundie Hu、Guobao Li、Chunchen Yuan、Zhi-Bin Huang、Da-Qing Shi、Yingsheng Zhao

  DOI：10.1021/acs.orglett.6b02773

  日期：2016.12.2

  of oxidative C–H/C–H cross-coupling of oxalyl amide-protected benzylamines and various heteroarenes in the presence of a rhodium(III) catalyst has been developed. The route provides a means of synthesizing ortho-heteroarylated benzylamines. The methodology presents broad substrate scope, great functional group tolerance, and good to excellent yields in the synthesis of substituted benzylamines. The

  在铑（III）催化剂存在下，草酰酰胺保护的苄胺和各种杂芳烃的氧化性C–H / C–H交叉偶联的第一个例子已经开发出来。该途径提供了合成邻杂芳基化苄胺的方法。该方法在取代苄胺的合成中具有宽泛的底物范围，强大的官能团耐受性以及良好至优异的收率。该研究还表明，噻吩异喹啉衍生物可通过将硫代苯基取代的苄胺与钯（II）分子内胺化而获得。
• [EN] COMPOUNDS HAVING BETA-AGONIST ACTIVITY<br/>[FR] COMPOSES PRESENTANT UNE ACTIVITE BETA-AGONISTE
  申请人：PFIZER LTD

  公开号：WO2005092841A1

  公开（公告）日：2005-10-06

  The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  本发明涉及化合物的公式（1）以及用于制备、制备中间体、含有和使用这些衍生物的过程。根据本发明的化合物在许多疾病、紊乱和情况中有用，特别是炎症性、过敏性和呼吸道疾病、紊乱和情况。
• Acetic acid as a catalyst for the N-acylation of amines using esters as the acyl source
  作者：Daniel D. Sanz Sharley、Jonathan M. J. Williams

  DOI：10.1039/c6cc09023k

  日期：——

  We report a cheap and simple method for the acetylation of a variety of amines using catalytic acetic acid and either ethyl acetate or butyl acetate as the acyl source....

  我们报告了一种廉价而简单的方法，该方法使用催化乙酸和乙酸乙酯或乙酸丁酯作为酰基源来乙酰化各种胺。