methyl 3-((3-methylphenyl)sulfonamido)thiophene-2-carboxylate | 663595-84-4

• 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-((3-methylphenyl)sulfonamido)thiophene-2-carboxylate
• 英文别名: Methyl 3-[(3-methylphenyl)sulfonylamino]thiophene-2-carboxylate
• CAS: 663595-84-4
• 化学式: C₁₃H₁₃NO₄S₂
• 分子量: 311.383
• InChiKey: DAUXUDAKRQFSSW-UHFFFAOYSA-N

物化性质

• 沸点：
  481.4±55.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-((3-methylphenyl)sulfonamido)thiophene-2-carboxylate 在 palladium diacetate 、 potassium carbonate 、 三甲基丙酮酸 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 2,4-滴二甲胺盐 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 methyl 1-(3-methoxyphenyl)-4-(m-tolylsulfonyl)-4,5-dihydrothieno[3,4-c]isoquinoline-3-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
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 、 间甲苯磺酰氯 在 吡啶 作用下， 反应 1.0h， 以83%的产率得到methyl 3-((3-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

• 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
• 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.