N-[(E)-2-(3-ethoxy-3-oxoprop-1-en-1-yl)-5-methyl-4-nitrobenzoyl]-S-methyl-S-phenylsulfoximine | 1616088-03-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-[(E)-2-(3-ethoxy-3-oxoprop-1-en-1-yl)-5-methyl-4-nitrobenzoyl]-S-methyl-S-phenylsulfoximine
• 英文别名: ethyl (E)-3-[4-methyl-2-[(methyl-oxo-phenyl-lambda6-sulfanylidene)carbamoyl]-5-nitrophenyl]prop-2-enoate；ethyl (E)-3-[4-methyl-2-[(methyl-oxo-phenyl-λ6-sulfanylidene)carbamoyl]-5-nitrophenyl]prop-2-enoate
• CAS: 1616088-03-9
• 化学式: C₂₀H₂₀N₂O₆S
• 分子量: 416.455
• InChiKey: PEGBKIGFDDKASW-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (甲基亚砜亚胺基)苯 在 4-二甲氨基吡啶 、 silver tetrafluoroborate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 copper(II) acetate monohydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 N-[(E)-2-(3-ethoxy-3-oxoprop-1-en-1-yl)-5-methyl-4-nitrobenzoyl]-S-methyl-S-phenylsulfoximine 、
  参考文献：
  名称：

  Sulfoximine-Directed Ruthenium-Catalyzed ortho-C–H Alkenylation of (Hetero)Arenes: Synthesis of EP3 Receptor Antagonist Analogue

  摘要：

  The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and alpha,beta-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.

  DOI：

  10.1021/jo5008465

文献信息

• Sulfoximine-Directed Ruthenium-Catalyzed <i>ortho</i>-C–H Alkenylation of (Hetero)Arenes: Synthesis of EP3 Receptor Antagonist Analogue
  作者：M. Ramu Yadav、Raja K. Rit、Majji Shankar、Akhila K. Sahoo

  DOI：10.1021/jo5008465

  日期：2014.7.3

  The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and alpha,beta-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.