3-benzyl-2-(2-bromophenylthiomethyl)-2,3-dihydro-3-hydroxy-1H-isoindol-1-one | 269742-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-benzyl-2-(2-bromophenylthiomethyl)-2,3-dihydro-3-hydroxy-1H-isoindol-1-one
• 英文别名: 3-Benzyl-2-[(2-bromophenyl)sulfanylmethyl]-3-hydroxyisoindol-1-one
• CAS: 269742-91-8
• 化学式: C₂₂H₁₈BrNO₂S
• 分子量: 440.36
• InChiKey: FTOKVPPFPHZIGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-2-(2-bromophenylthiomethyl)-2,3-dihydro-3-hydroxy-1H-isoindol-1-one 在 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 12.03h， 生成 11b,12-dihydro-5,11b-(6'-bromothioepoxy[1',2']benzeno)-5H-isoindolo[2,1-b]isoquinolin-7-one
  参考文献：
  名称：

  Formation of New 5,11b-Bridged Isoindolo[2,1-b]isoquinolinones Alkaloids through a Tandem Pummerer/π-Cationic Cyclization

  摘要：

  The tandem Pummerer/pi-aromatic cyclization of alpha-acyliminium ion, leading efficiently in "one pot" to thioepoxyareno-bridged isoindoloisoquinolinone incorporating the arylthio group, has been demonstrated for the first time. During this sequence the angular hydroxylated isoindoloisoquinolinone, resulting from the Pummerer-type cyclization, was also obtained.

  DOI：

  10.1021/ol005545c
• 作为产物：
  描述：

  2-溴硫代苯酚 在 sodium methylate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-benzyl-2-(2-bromophenylthiomethyl)-2,3-dihydro-3-hydroxy-1H-isoindol-1-one
  参考文献：
  名称：

  Formation of New 5,11b-Bridged Isoindolo[2,1-b]isoquinolinones Alkaloids through a Tandem Pummerer/π-Cationic Cyclization

  摘要：

  The tandem Pummerer/pi-aromatic cyclization of alpha-acyliminium ion, leading efficiently in "one pot" to thioepoxyareno-bridged isoindoloisoquinolinone incorporating the arylthio group, has been demonstrated for the first time. During this sequence the angular hydroxylated isoindoloisoquinolinone, resulting from the Pummerer-type cyclization, was also obtained.

  DOI：

  10.1021/ol005545c

文献信息

• Formation of New 5,11b-Bridged Isoindolo[2,1-<i>b</i>]isoquinolinones Alkaloids through a Tandem Pummerer/π-Cationic Cyclization
  作者：Nicolas Hucher、Adam Daich、Bernard Decroix

  DOI：10.1021/ol005545c

  日期：2000.5.1

  The tandem Pummerer/pi-aromatic cyclization of alpha-acyliminium ion, leading efficiently in "one pot" to thioepoxyareno-bridged isoindoloisoquinolinone incorporating the arylthio group, has been demonstrated for the first time. During this sequence the angular hydroxylated isoindoloisoquinolinone, resulting from the Pummerer-type cyclization, was also obtained.