5-cyano-3,6-bis(diphenylmethyl)-3-hydroxy-2-methylisoindol-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 5-cyano-3,6-bis(diphenylmethyl)-3-hydroxy-2-methylisoindol-1-one
• 英文别名: 3,6-Dibenzhydryl-3-hydroxy-2-methyl-1-oxoisoindole-5-carbonitrile
• 化学式: C₃₆H₂₈N₂O₂
• 分子量: 520.631
• InChiKey: XGJJPBJBDQIOKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  均苯四甲酸 在 氢氧化钾 、 ammonium hydroxide 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.75h， 生成 5-cyano-3,6-bis(diphenylmethyl)-3-hydroxy-2-methylisoindol-1-one
  参考文献：
  名称：

  Photochemical reaction of phthalimides and dicyanophthalimides with benzylic donors

  摘要：

  Irradiation of phthalimides in the presence of benzylic donors PhCRHX (R=H, Ph, X=H, SiMe3, CHPh2, CHOCH2CH2O) proceeds via electron transfer and radical cation cleavage, resulting in benzylation at the carboximide moiety to yield 3-benzyl-3-hydroxyisoindol-1-ones. With 4,5-dicyanophthalimides substitution of benzyl for a cyano group is a competitive, and in some cases predominating, pathway. A rationalization is proposed on the basis of the in cage vs out of cage radical cation cleavage. In the first mechanism, the radical anion of the dicyanophthalimide, where spin and charge are differently located, probably assists the radical cation fragmentation.

  DOI：

  10.1021/jo00059a023

文献信息

• Photochemical reaction of phthalimides and dicyanophthalimides with benzylic donors
  作者：Mauro Freccero、Elisa Fasani、Angelo Albini

  DOI：10.1021/jo00059a023

  日期：1993.3

  Irradiation of phthalimides in the presence of benzylic donors PhCRHX (R=H, Ph, X=H, SiMe3, CHPh2, CHOCH2CH2O) proceeds via electron transfer and radical cation cleavage, resulting in benzylation at the carboximide moiety to yield 3-benzyl-3-hydroxyisoindol-1-ones. With 4,5-dicyanophthalimides substitution of benzyl for a cyano group is a competitive, and in some cases predominating, pathway. A rationalization is proposed on the basis of the in cage vs out of cage radical cation cleavage. In the first mechanism, the radical anion of the dicyanophthalimide, where spin and charge are differently located, probably assists the radical cation fragmentation.