dimethyl 2-(cyanomethyl)-2-(3-(2-((4-methylphenyl)sulfonamido)-5-(trifluoromethyl)phenyl)prop-2-yn-1-yl)malonate | 1582321-34-3

• 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: dimethyl 2-(cyanomethyl)-2-(3-(2-((4-methylphenyl)sulfonamido)-5-(trifluoromethyl)phenyl)prop-2-yn-1-yl)malonate
• CAS: 1582321-34-3
• 化学式: C₂₄H₂₁F₃N₂O₆S
• 分子量: 522.502
• InChiKey: CDUGZUDUCGQJOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122.56
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(cyanomethyl)-2-(3-(2-((4-methylphenyl)sulfonamido)-5-(trifluoromethyl)phenyl)prop-2-yn-1-yl)malonate 在 2,2'-联吡啶 、 palladium diacetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以75%的产率得到dimethyl 4-oxo-9-tosyl-6-(trifluoromethyl)-1,3,4,9-tetrahydro-2H-carbazole-2,2-dicarboxylate
  参考文献：
  名称：

  Pd(II)-Catalyzed One-Step Construction of Cycloalkane-Fused Indoles and Its Application in Formal Synthesis of (±)-Aspidospermidine

  摘要：

  A highly efficient, redox-free Pd(II)-catalyzed tandem cyclization reaction initiated by intramolecular amino-palladation of alkynes followed by nucleophilic addition to nitrites is developed. This method provides a versatile approach for the synthesis of six- to eight-membered ring-fused indoles in one step and has also shown advantages in the formal synthesis of (+/-)-aspidospermidine.

  DOI：

  10.1021/ol500662f
• 作为产物：
  描述：

  4-氨基-3-碘三氟甲苯 在 吡啶 、 copper(l) iodide 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 dimethyl 2-(cyanomethyl)-2-(3-(2-((4-methylphenyl)sulfonamido)-5-(trifluoromethyl)phenyl)prop-2-yn-1-yl)malonate
  参考文献：
  名称：

  Pd(II)-Catalyzed One-Step Construction of Cycloalkane-Fused Indoles and Its Application in Formal Synthesis of (±)-Aspidospermidine

  摘要：

  A highly efficient, redox-free Pd(II)-catalyzed tandem cyclization reaction initiated by intramolecular amino-palladation of alkynes followed by nucleophilic addition to nitrites is developed. This method provides a versatile approach for the synthesis of six- to eight-membered ring-fused indoles in one step and has also shown advantages in the formal synthesis of (+/-)-aspidospermidine.

  DOI：

  10.1021/ol500662f