methyl 3-((N-(2-bromobenzyl)-4-methylphenyl)sulfonamido)thiophene-2-carboxylate | 1374831-17-0

• 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: methyl 3-((N-(2-bromobenzyl)-4-methylphenyl)sulfonamido)thiophene-2-carboxylate
• 英文别名: Methyl 3-[(2-bromophenyl)methyl-(4-methylphenyl)sulfonylamino]thiophene-2-carboxylate；methyl 3-[(2-bromophenyl)methyl-(4-methylphenyl)sulfonylamino]thiophene-2-carboxylate
• CAS: 1374831-17-0
• 化学式: C₂₀H₁₈BrNO₄S₂
• 分子量: 480.403
• InChiKey: JTTYIMKHTDNITC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-((N-(2-bromobenzyl)-4-methylphenyl)sulfonamido)thiophene-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 水 、 caesium carbonate 、 溶剂黄146 、 sodium hydroxide 、 palladium dichloride 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.13h， 生成 2-bromo-4-tosyl-4,5-dihydrothieno[3,2-c]isoquinoline
  参考文献：
  名称：

  Design, structure-activity relationship study and biological evaluation of the thieno[3,2-c]isoquinoline scaffold as a potential anti-cancer agent

  摘要：

  DOI：

  10.1016/j.bmcl.2021.128327
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 methyl 3-((N-(2-bromobenzyl)-4-methylphenyl)sulfonamido)thiophene-2-carboxylate
  参考文献：
  名称：

  A One-Pot Double C–H Activation Palladium Catalyzed Route to a Unique Class of Highly Functionalized Thienoisoquinolines

  摘要：

  The synthesis of a unique class of highly functionalized 3,4-thienoisoquinolines via an efficient palladium-catalyzed one-pot, regioselective double C H activation is presented. This class of biologically relevant compounds has been prepared in five steps from commercially available starting materials with overall yields ranging from 27 to 62%. A masked carboxylic acid was used to direct C H activation to the typically less reactive C4 position. Additionally, the carboxylic acid provides a synthetically useful handle for further functionalization.

  DOI：

  10.1021/ol3009655

文献信息

• A One-Pot Double C–H Activation Palladium Catalyzed Route to a Unique Class of Highly Functionalized Thienoisoquinolines
  作者：Nicholas W. Y. Wong、Pat Forgione

  DOI：10.1021/ol3009655

  日期：2012.6.1

  The synthesis of a unique class of highly functionalized 3,4-thienoisoquinolines via an efficient palladium-catalyzed one-pot, regioselective double C H activation is presented. This class of biologically relevant compounds has been prepared in five steps from commercially available starting materials with overall yields ranging from 27 to 62%. A masked carboxylic acid was used to direct C H activation to the typically less reactive C4 position. Additionally, the carboxylic acid provides a synthetically useful handle for further functionalization.
• Design, structure-activity relationship study and biological evaluation of the thieno[3,2-c]isoquinoline scaffold as a potential anti-cancer agent
  作者：Jiang Tian Liu、Dilan B. Jaunky、Kevin Larocque、Fei Chen、Keegan Mckibbon、Mehdi Sirouspour、Sarah Taylor、Alexandre Shafeii、Donald Campbell、Helena Braga、Alisa Piekny、Pat Forgione

  DOI：10.1016/j.bmcl.2021.128327

  日期：2021.11