N-((2,5-dimethoxyphenyl)sulfonyl)acetamide | 28011-66-7

• 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: N-((2,5-dimethoxyphenyl)sulfonyl)acetamide
• 英文别名: N-Acetyl-2,5-dimethoxy-benzolsulfonamid；N-(2,5-dimethoxyphenyl)sulfonylacetamide
• CAS: 28011-66-7
• 化学式: C₁₀H₁₃NO₅S
• 分子量: 259.283
• InChiKey: ZGKMJMWNOXBBAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-((2,5-dimethoxyphenyl)sulfonyl)acetamide 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Identification of benzofused five-membered sultams, potent dual NOD1/NOD2 antagonists in vitro and in vivo

  摘要：

  Nucleotide-binding oligomerization domain-containing proteins 1 and 2 play important roles in immune system activation. Recently, a shift has occurred due to the emerging knowledge that preventing nucleotide-binding oligomerization domains (NODs) signaling could facilitate the treatment of some cancers, which warrants the search for dual antagonists of NOD1 and NOD2. Herein, we undertook the synthesis and identification of a new class of derivatives of dual NOD1/NOD2 antagonists with novel benzofused five-membered sultams. Compound 14k was finally demonstrated to be the most potent molecule that inhibits both NOD1-and NOD2-stimulated NF-kappa B and MAPK signaling in vitro and in vivo. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112575
• 作为产物：
  描述：

  2,5-二甲氧基苯磺胺 、 乙酸酐 在 zinc(II) chloride 作用下， 以92%的产率得到N-((2,5-dimethoxyphenyl)sulfonyl)acetamide
  参考文献：
  名称：

  铑（iii）催化的磺酰胺通过金属卡宾迁移插入而指导邻位C–H类胡萝卜素官能化†

  摘要：

  铑（III）催化的磺酰胺定向的邻位C-H类胡萝卜素官能化已经得到了良好的收率。该方法由于其广泛的底物范围而具有吸引力，并且能够衍生出多种生物活性的磺酰胺结构和磺胺药物的后期修饰。

  DOI：

  10.1039/c8cc08837c

文献信息

• Ruthenium-Catalyzed Selectively Oxidative C–H Alkenylation of <i>N</i>-Acylated Aryl Sulfonamides by Using Molecular Oxygen as an Oxidant
  作者：Xueyuan Li、Xiao Hu、Zijie Liu、Jingshu Yang、Bo Mei、Yi Dong、Gang Liu

  DOI：10.1021/acs.joc.0c00242

  日期：2020.5.1

  A ruthenium-catalyzed sulfonamide-directed ortho aryl C-H alkenylation/annulation to afford five-membered sultam by using of molecular oxygen as an oxidant is reported in this article. Compared to the previous transition-metal-catalyzed C-H alkenylation of aryl sulfonamides, no excess metal salt oxidant was required in this method. A wide sulfonamide substrates scope and good regioselectivity and site-selectivity

  本文报道了以分子氧为氧化剂，钌催化磺酰胺定向邻芳基 CH 烯基化/环化得到五元苏丹坦。与之前的过渡金属催化芳基磺酰胺的 CH 烯基化相比，该方法不需要过量的金属盐氧化剂。广泛的磺酰胺底物范围和良好的区域选择性和位点选择性使这种Ru催化方法更具吸引力。重要的是，该方法不仅可以有效制备具有生物活性的五元舒坦分子，还可以有效地应用于磺胺类药物的后期修饰。
• Synthesis of Benzofused Five-Ring Sultams via Rh-Catalyzed C–H Olefination Directed by an <i>N</i>-Ac-Substituted Sulfonamide Group
  作者：Xueyuan Li、Yi Dong、Fengyu Qu、Gang Liu

  DOI：10.1021/jo502224d

  日期：2015.1.16

  A Rh-catalyzed N-Ac-sulfonamide group directed C-H olefination-cyclization to afford benzofused five-ring sultam is described with high yield and a wide range of substrate scope. The N-acetyl group is a key for this transformation implying that N-H acidity is the major influence. The acetyl group is removed under mild conditions in excellent yield to provide NH-free sultam that can be transformed into various benzofused five-ring sultam analogues via acylation, nucleophilic substitution, and Mitsunobu alkylation.