9-benzoyl-2-vinylsulfonyl-1,2,3,4-tetrahydro-9H-carbazole | 137304-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-benzoyl-2-vinylsulfonyl-1,2,3,4-tetrahydro-9H-carbazole
• 英文别名: (2-ethenylsulfonyl-1,2,3,4-tetrahydrocarbazol-9-yl)-phenylmethanone
• CAS: 137304-25-7
• 化学式: C₂₁H₁₉NO₃S
• 分子量: 365.453
• InChiKey: CVXYZNZLCCKFRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  二乙烯基砜 、 N-benzoylindolo-2,3-quinodimethane 在 4 A molecular sieve 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.5h， 以14%的产率得到9-benzoyl-2-vinylsulfonyl-1,2,3,4-tetrahydro-9H-carbazole
  参考文献：
  名称：

  Diels-Alder Reactions ofin situ generated N-benzoylindolo-2,3-quinodimethane with carbodienophiles

  摘要：

  The indolo-2,3-quinodimethane (5), generated from 2,3-bis(bromomethyl)indole (4), was trapped with unsymmetrical carbodienophiles or N,N'-p-phenylenedimaleimide to furnish the 1,2,3,4-tetrahydrocarbazoles (6 - 9). [4 + 2]-Cycloaddition of 5 with tetracyanoethylene gave rise to the tetracyanocarbazole (10) and a subsequent product 11 a or 11 b. The Diels-Alder reaction of 5 with divinyl sulfone was regiospecific within the detection limits of HPLC analysis. Similarly, the reaction of 5 with N,N'-p-phenylenedimaleimide yielded solely the stereoisomer 9.

  DOI：

  10.1002/prac.19933350103

文献信息

• Diels-Alder Reactions under Molecular Sieve Catalysis: Enhancement of Reactivity in Cyclization Reactions with N-Benzoylindole-2,3-quinodimethane to Functionalized Carbazoles
  作者：Ulf Pindur、Manfred Haber

  DOI：10.3987/com-91-5776

  日期：——

  In the presence of highly activated molecular sieves (4 A0), the Diels-Alder reactivity of in situ generated N-benzoylindole-2,3-quinodimethane is enhanced considerably. Reactions of this species with a variety of carbodienophiles give rise to novel functionalized and [b]annelated carbazole derivatives in a one-pot procedure.