3',3',4',4'-tetramethylspiro<1,3-dihydroisobenzofuran-1,2'-thietane> | 141636-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 3',3',4',4'-tetramethylspiro<1,3-dihydroisobenzofuran-1,2'-thietane>
• 英文别名: 3',3',4',4'-tetramethylspiro(1,3-dihydroisobenzofuran-1,2'-thietane)；2',2',3',3'-tetramethylspiro[1H-2-benzofuran-3,4'-thietane]
• CAS: 141636-35-3
• 化学式: C₁₄H₁₈OS
• 分子量: 234.362
• InChiKey: IMULHRRPMXEZAG-UHFFFAOYSA-N

物化性质

• 沸点：
  329.5±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3',3',4',4'-tetramethylspiro<1,3-dihydroisobenzofuran-1,2'-thietane> 以 甲苯 为溶剂， 反应 15.0h， 以20%的产率得到3,3,4,4-tetramethyl-1,3,4,5-tetrahydro-1,5-epoxy-2-benzothiepine
  参考文献：
  名称：

  Nishio, Takehiko, Journal of the Chemical Society. Perkin transactions I, 1995, # 5, p. 561 - 568

  摘要：

  DOI：
• 作为产物：
  描述：

  3H-isobenzofuran-1-thione 、 2,3-二甲基-2-丁烯 以 苯 为溶剂， 以80%的产率得到3',3',4',4'-tetramethylspiro<1,3-dihydroisobenzofuran-1,2'-thietane>
  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

• 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.
• Nishio, Takehiko, Journal of the Chemical Society. Perkin transactions I, 1995, # 5, p. 561 - 568
  作者：Nishio, Takehiko

  DOI：——

  日期：——