3-(8-methoxy-2,3,5,6-tetrahydro-1,7-dithia-s-indacen-4-yl)-N,N-dimethylacrylamide

• 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: 3-(8-methoxy-2,3,5,6-tetrahydro-1,7-dithia-s-indacen-4-yl)-N,N-dimethylacrylamide
• 英文别名: (E)-3-(8-methoxy-2,3,5,6-tetrahydrothieno[3,2-f][1]benzothiol-4-yl)-N,N-dimethylprop-2-enamide
• 化学式: C₁₆H₁₉NO₂S₂
• 分子量: 321.464
• InChiKey: JFMXEAPWRRCCNP-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[3-(2-hydroxyethylsulfanyl)-5-iodo-2-methoxyphenylsulfanyl]ethanol 在 palladium diacetate 降冰片烯 、 溴 、 caesium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 3-(8-methoxy-2,3,5,6-tetrahydro-1,7-dithia-s-indacen-4-yl)-N,N-dimethylacrylamide
  参考文献：
  名称：

  Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence

  摘要：

  A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.

  DOI：

  10.1021/jo0617868

文献信息

• Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence
  作者：Dino Alberico、Alena Rudolph、Mark Lautens

  DOI：10.1021/jo0617868

  日期：2007.2.1

  A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.