N-isopentyl-4-methoxybenzenesulfonamide | 349085-98-9

• 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: N-isopentyl-4-methoxybenzenesulfonamide
• 英文别名: 4-methoxy-N-(3-methylbutyl)benzenesulfonamide
• CAS: 349085-98-9
• 化学式: C₁₂H₁₉NO₃S
• 分子量: 257.354
• InChiKey: HRTQYAYITGJEQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-isopentyl-4-methoxybenzenesulfonamide 在 2,2'-联吡啶 、 caesium bromide 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.5h， 生成 4-methoxy-N-(3-methyl-4-((trifluoromethyl)thio)butyl)benzenesulfonamide
  参考文献：
  名称：

  Copper-Catalyzed, N-Directed Csp³–H Trifluoromethylthiolation (−SCF₃) and Trifluoromethylselenation (−SeCF₃)

  摘要：

  A direct and versatile copper-catalyzed trifluoromethylthiolation and trifluoromethylselenation of primary, secondary, and tertiary aliphatic C-H bonds was developed. The reaction provides direct access to molecules containing these emerging moieties in the presence of a wide range of common functional groups and in complex molecular environments.

  DOI：

  10.1021/jacs.9b10316
• 作为产物：
  描述：

  异戊胺 、 对甲氧基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以94%的产率得到N-isopentyl-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  Copper-Catalyzed, N-Directed Csp³–H Trifluoromethylthiolation (−SCF₃) and Trifluoromethylselenation (−SeCF₃)

  摘要：

  A direct and versatile copper-catalyzed trifluoromethylthiolation and trifluoromethylselenation of primary, secondary, and tertiary aliphatic C-H bonds was developed. The reaction provides direct access to molecules containing these emerging moieties in the presence of a wide range of common functional groups and in complex molecular environments.

  DOI：

  10.1021/jacs.9b10316

文献信息

• Discovery of CGS 27023A, a Non-Peptidic, Potent, and Orally Active Stromelysin Inhibitor That Blocks Cartilage Degradation in Rabbits
  作者：Lawrence J. MacPherson、Erol K. Bayburt、Michael P. Capparelli、Brian J. Carroll、Robert Goldstein、Michael R. Justice、Lijuan Zhu、Shou-ih Hu、Richard A. Melton、Lynn Fryer、Ron L. Goldberg、John R. Doughty、Salvatore Spirito、Vincent Blancuzzi、Doug Wilson、Elizabeth M. O'Byrne、Vishwas Ganu、David T. Parker

  DOI：10.1021/jm960871c

  日期：1997.8.1

  Structure-activity relationships of a lead hydroxamic acid inhibitor of recombinant human stromelysin were systematically defined by taking advantage of a concise synthesis that allowed diverse functionality to be explored at each position in a template. An ex vivo rat model and an in vivo rabbit model of stromelysin-induced cartilage degradation were used to further optimize these analogs for oral activity and duration of action. The culmination of these modifications resulted in CGS 27023A, a potent, orally active stromelysin inhibitor that blocks the erosion of cartilage matrix.
• Copper-Catalyzed, N-Directed Csp³–H Trifluoromethylthiolation (−SCF₃) and Trifluoromethylselenation (−SeCF₃)
  作者：Atanu Modak、Emily N. Pinter、Silas P. Cook

  DOI：10.1021/jacs.9b10316

  日期：2019.11.20

  A direct and versatile copper-catalyzed trifluoromethylthiolation and trifluoromethylselenation of primary, secondary, and tertiary aliphatic C-H bonds was developed. The reaction provides direct access to molecules containing these emerging moieties in the presence of a wide range of common functional groups and in complex molecular environments.