1-Hydroxy-1-phenyl-2-<(trimethylsilyl)methyl>isoindolinone | 153397-44-5

• 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: 1-Hydroxy-1-phenyl-2-<(trimethylsilyl)methyl>isoindolinone
• 英文别名: 3-Hydroxy-3-phenyl-2-(trimethylsilylmethyl)isoindol-1-one
• CAS: 153397-44-5
• 化学式: C₁₈H₂₁NO₂Si
• 分子量: 311.456
• InChiKey: OEJXWGUNFGNNGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Hydroxy-1-phenyl-2-<(trimethylsilyl)methyl>isoindolinone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以78%的产率得到1-Phenyl-2-<(triethylsilyl)methyl>isoindole
  参考文献：
  名称：

  Rearrangement of cis and trans-2-methyl-1-(substituted phenyl)isoindolinium 2-methylides

  摘要：

  Fluoride ion induced desilylation of cis-2-methyl-1-(substituted phenyl)-2-[(trimethylsilyl)methyl] isoindolinium iodides cis-5 gave mixtures of the Sommelet-Hauser rearrangement products 7 and the Stevens products 8 in a ratio about 8.5:1.5. Similar treatments of the trans-isomers (trans-5) afforded exclusively 8. The pathways of the ylide rearrangement are discussed.

  DOI：

  10.1021/jo00080a024
• 作为产物：
  描述：

  溴苯 、 N-(三甲基硅基甲基)酰亚胺 在 lithium 作用下， 以83%的产率得到1-Hydroxy-1-phenyl-2-<(trimethylsilyl)methyl>isoindolinone
  参考文献：
  名称：

  Rearrangement of cis and trans-2-methyl-1-(substituted phenyl)isoindolinium 2-methylides

  摘要：

  Fluoride ion induced desilylation of cis-2-methyl-1-(substituted phenyl)-2-[(trimethylsilyl)methyl] isoindolinium iodides cis-5 gave mixtures of the Sommelet-Hauser rearrangement products 7 and the Stevens products 8 in a ratio about 8.5:1.5. Similar treatments of the trans-isomers (trans-5) afforded exclusively 8. The pathways of the ylide rearrangement are discussed.

  DOI：

  10.1021/jo00080a024

文献信息

• Rearrangement of cis and trans-2-methyl-1-(substituted phenyl)isoindolinium 2-methylides
  作者：Akira Sakuragi、Naohiro Shirai、Yoshiro Sato、Yukihisa Kurono、Keiichiro Hatano

  DOI：10.1021/jo00080a024

  日期：1994.1

  Fluoride ion induced desilylation of cis-2-methyl-1-(substituted phenyl)-2-[(trimethylsilyl)methyl] isoindolinium iodides cis-5 gave mixtures of the Sommelet-Hauser rearrangement products 7 and the Stevens products 8 in a ratio about 8.5:1.5. Similar treatments of the trans-isomers (trans-5) afforded exclusively 8. The pathways of the ylide rearrangement are discussed.