2-(4-甲氧基苯基)-3H-异吲哚-1-硫酮 | 89313-77-9

• 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
• 中文名称: 2-(4-甲氧基苯基)-3H-异吲哚-1-硫酮
• 英文名称: 2-(p-anisyl)isoindoline-1-thione
• 英文别名: 2-(4-Methoxyphenyl)-2,3-dihydro-1H-isoindole-1-thione；2-(4-methoxyphenyl)-3H-isoindole-1-thione
• CAS: 89313-77-9
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: CTDCQFXNFYWDFW-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C(Solv: isopropanol (67-63-0))
• 沸点：
  410.6±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基)-3H-异吲哚-1-硫酮 以50%的产率得到
  参考文献：
  名称：

  KOVTUNENKO, V. A.;DOBRENKO, T. T.;VOJTENKO, Z. V.;TYLTIN, A. K.;BABICHEV,+, XIMIYA GETEROTSIKL. SOEDIN., 1984, N 9, 1200-1205

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-methoxyphenyl)isoindolin-1-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 2-(4-甲氧基苯基)-3H-异吲哚-1-硫酮
  参考文献：
  名称：

  Photoreactions of isoindoline-1-thiones with alkenes: unusual formation of tricyclic isoindolines

  摘要：

  Photochemical cycloaddition reactions of cyclic thioamides and alkenes have been examined. Irradiation of 2-arylisoindoline-1-thiones 1 in the presence of alkenes 2 gave the unexpected tricyclic isoindolines 3-18. The formation of tricyclic isoindolines can best be explained in terms of the intermediacy of aminospirothietane 27, formed by [2 + 2] photocycloaddition of the C=S double bond of 1 to the C=C double bond of 2. Ring cleavage of the resultant amino thietane, assisted by the participation of the nitrogen lone-pair electrons, produced zwitterions 28 and 29 or 1-mercaptoethylisoindole (30). Subsequent nucleophilic attack of the thiol anion on the iminium carbon of 29 or attack of the thiol group on C-3 of 30 gave the final products. Irradiation of isobenzofuran-1-thione (22) and isobenzothiophene-l-thione (23) in the presence of tetramethylethylene (2a) gave the corresponding spirothietanes 24 and 25.

  DOI：

  10.1021/jo00040a049

文献信息

• 1-Ethylthio-2R-isoindoles. An example of nonsynchronous addition in the diels-alder reaction
  作者：V. A. Kovtunenko、T. T. Dobrenko、Z. V. Voitenko、A. K. Tyltin、F. S. Babichev

  DOI：10.1007/bf00506392

  日期：1984.9
• KOVTUNENKO, V. A.;TYLTIN, A. K.;DOBRENKO, T. T.;BABICHEV, F. S., YKP. XIM. ZH., 1983, 49, N 10, 1099-1103
  作者：KOVTUNENKO, V. A.、TYLTIN, A. K.、DOBRENKO, T. T.、BABICHEV, F. S.

  DOI：——

  日期：——
• Photoreactions of isoindoline-1-thiones with alkenes: unusual formation of tricyclic isoindolines
  作者：Takehiko Nishio、Norikazu Okuda

  DOI：10.1021/jo00040a049

  日期：1992.7

  Photochemical cycloaddition reactions of cyclic thioamides and alkenes have been examined. Irradiation of 2-arylisoindoline-1-thiones 1 in the presence of alkenes 2 gave the unexpected tricyclic isoindolines 3-18. The formation of tricyclic isoindolines can best be explained in terms of the intermediacy of aminospirothietane 27, formed by [2 + 2] photocycloaddition of the C=S double bond of 1 to the C=C double bond of 2. Ring cleavage of the resultant amino thietane, assisted by the participation of the nitrogen lone-pair electrons, produced zwitterions 28 and 29 or 1-mercaptoethylisoindole (30). Subsequent nucleophilic attack of the thiol anion on the iminium carbon of 29 or attack of the thiol group on C-3 of 30 gave the final products. Irradiation of isobenzofuran-1-thione (22) and isobenzothiophene-l-thione (23) in the presence of tetramethylethylene (2a) gave the corresponding spirothietanes 24 and 25.
• KOVTUNENKO, V. A.;DOBRENKO, T. T.;VOJTENKO, Z. V.;TYLTIN, A. K.;BABICHEV,+, XIMIYA GETEROTSIKL. SOEDIN., 1984, N 9, 1200-1205
  作者：KOVTUNENKO, V. A.、DOBRENKO, T. T.、VOJTENKO, Z. V.、TYLTIN, A. K.、BABICHEV,+

  DOI：——

  日期：——