3-Methyl-2-phenyl-1-isoindolinethione | 123217-52-7

• 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-Methyl-2-phenyl-1-isoindolinethione
• 英文别名: 3-methyl-2-phenyl-3H-isoindole-1-thione
• CAS: 123217-52-7
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: LAYIDAMUGKMUAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Methyl-2-phenyl-1-isoindolinethione 在 镍 作用下， 以 甲醇 、 苯 为溶剂， 反应 1.0h， 生成 1-(1',1',2'-trimethyl-2'-propenyl)-phenyl-3-methylisoindoline
  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
• 作为产物：
  描述：

  2-乙酰苯甲酸 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 15.25h， 生成 3-Methyl-2-phenyl-1-isoindolinethione
  参考文献：
  名称：

  Nishio, Takehiko; Yamamoto, Hiroshi, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 883 - 892

  摘要：

  DOI：

文献信息

• Reaction of 3-Hydroxyisoindolin-1-ones with Lawesson Reagent. Synthesis of Isoindoline-1-thiones
  作者：Takehiko Nishio、Norikazu Okuda、Yo-ichi Mori、Choji Kashima

  DOI：10.1055/s-1989-27264

  日期：——

  Treatment of 3-hydroxyisoindolin-1-ones 1 with Lawesson reagent gave isoindoline-1-thiones 2, by direct thionation and reductive elimination of hydroxy group, in good yields.

  用 Lawesson 试剂处理 3-羟基异吲哚啉-1-酮 1，通过直接硫化和还原消除羟基，得到异吲哚啉-1-硫酮 2，收率良好。
• NISHIO, TAKEHIKO;OKUDA, NORIKAZU;MORI, YO-ICHI;KASHIMA, CHOJI, SYNTHESIS,(1989) N, C. 396-397
  作者：NISHIO, TAKEHIKO、OKUDA, NORIKAZU、MORI, YO-ICHI、KASHIMA, CHOJI

  DOI：——

  日期：——
• Nishio, Takehiko; Yamamoto, Hiroshi, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 883 - 892
  作者：Nishio, Takehiko、Yamamoto, Hiroshi

  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.