2,6-dimethoxy-N-phenylbenzamide | 1466-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dimethoxy-N-phenylbenzamide
• CAS: 1466-77-9
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: AVVOMQBZPZJLJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxy-N-phenylbenzamide 在 氢化钾 、 氯化铵 作用下， 以 四氢呋喃 、 氨 、 叔丁醇 为溶剂， 以99%的产率得到2,6-Dimethoxy-cyclohexa-2,5-dienecarboxylic acid phenylamide
  参考文献：
  名称：

  A convenient synthesis of 2-methyl-3-oxoheptane-1,7-dicarboxylic esters and amides

  摘要：

  A range of simple derivatives of 2-methyl-3-oxoheptane-1,7-dicarboxylic acid have been prepared by Birch reduction/ methylation of 2,6-dimethoxybenzoic acid derivatives followed by solvolysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.067
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 在 N-甲基吡咯烷酮 、 palladium(II) trifluoroacetate 、 6-甲基-2,2′-二吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 7.33h， 生成 2,6-dimethoxy-N-phenylbenzamide
  参考文献：
  名称：

  钯介导的CO 2挤出，然后插入异氰酸酯以合成苯甲酰胺：翻译基本的机理研究以开发催化方案

  摘要：

  本文介绍了化学计量的钯介导的芳香族羧酸的ExIn（ExIn =挤出-插入）脱羧酰胺化反应的机理，提供了气相和冷凝相的光谱数据，并为拟议的逐步过程中的中间体提供了理论计算证据。从这些机理研究中获得的理解指导了钯催化方法的开发，在该方法中，在一锅30分钟的微波辐照辅助实验中，苯甲酰胺的产率高至高。实验数据和DFT计算的结合表明，某些配体添加剂有利于苯甲酰胺的选择性形成，而不是不需要的原羧化副产物。

  DOI：

  10.1021/acs.organomet.9b00820

文献信息

• New activation of carboxylic acids by reaction with N,N-bis-(2-oxo-3-oxazolidinyl) phosphorodiamidic chloride (ClsPO)
  作者：Juan Cabré-Castellví、Antonio Luis Palomo-Coll

  DOI：10.1016/s0040-4039(00)93682-7

  日期：1980.1

  Pentacoordinated and quinquevalent phosphorus intermediates, have been isolated by reaction between the title reagent and carboxylic acids, prior to conversion into amides.

  在转化为酰胺之前，已通过标题试剂与羧酸之间的反应分离出五配位和五价的磷中间体。
• An efficient magnetic copper ferrite nanoparticle catalysed ligand and solvent free synthesis of N-aryl amide from aldoximes and iodobenzene
  作者：Sachin A. Sarode、Jeevan M. Bhojane、Jayashree M. Nagarkar

  DOI：10.1039/c5ra22777a

  日期：——

  A one pot dehydration, hydration and coupling reaction protocol for N-substituted amide formation.

  一种用于N-取代酰胺形成的一锅脱水、水合和偶联反应方案。
• A one-pot route to thioamides discovered by gas-phase studies: palladium-mediated CO₂ extrusion followed by insertion of isothiocyanates
  作者：Asif Noor、Jiawei Li、George N. Khairallah、Zhen Li、Hossein Ghari、Allan J. Canty、Alireza Ariafard、Paul S. Donnelly、Richard A. J. O'Hair

  DOI：10.1039/c7cc00865a

  日期：——

  A new palladium mediated "one pot" synthesis of thioamides from aromatic carboxylic acids (ArCO2H + RNCS [rightward arrow] ArC(S)NHR + CO2) was discovered by gas-phase experiments and theoretical studies. Palladium-mediated decarboxylation...

  通过气相实验和理论研究发现了一种新的钯介导的“一锅法”从芳族羧酸（Ar H + RNCS [右箭头] ArC（S）NHR + CO2）合成硫酰胺的方法。钯介导的脱羧反应
• GB1017975
  申请人：——

  公开号：——

  公开（公告）日：——
• Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin
  作者：Sang Yoon Choi、Sanghee Kim、Jae Sung Hwang、Byeong Gon Lee、Hocheol Kim、Sun Yeou Kim

  DOI：10.1016/j.bcp.2003.09.045

  日期：2004.2

  This study evaluated the effects of synthetic benzylamide compound I (2,6-dimethoxy-N-phenylbenzamide) on the ultraviolet B (UV B)-induced hyperpigmentation. of the skin. UV B-induced hyperpigmentation was elicited on brownish guinea pig skin according to the method reported by Hideya et al. [Arch Dermatol Res 290 (1998) 375] with minor modifications. A lightening effect was observed following the topical application of compound I on UV-stimulated hyperpigmentation. The skin returned to its original color after treatment with compound I. Fontana-Masson staining indicated that melanin level in the hyperpigmented area was significantly decreased in the compound I-treated animals. However, the number of melanocytes were not changed in the compound I-treated groups using the S-100 stain, which is an immunohistochemical method. In vitro experiments using the cultured melanoma cells showed a 31.7% inhibition of melanin production by compound 1 at 100 muM. In addition, this compound had no effect on the tyrosinase enzyme function. However, it exhibited a catalyzing effect on the dopachrome transformation into 5,6-dihydroxyindole-2-carboxylic acid. Overall, the pigment-lightening effects of the compound I may due to the dopachrome tautomerase stimulation. (C) 2003 Elsevier Inc. All rights reserved.