N-(p-methoxybenzyl) 3,4-dimethoxyphthalimide | 462085-28-5

• 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: N-(p-methoxybenzyl) 3,4-dimethoxyphthalimide
• 英文别名: 4,5-Dimethoxy-2-[(4-methoxyphenyl)methyl]isoindole-1,3-dione
• CAS: 462085-28-5
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: ZKZBWRAEWAUMCA-UHFFFAOYSA-N

物化性质

• 沸点：
  507.0±50.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(p-methoxybenzyl) 3,4-dimethoxyphthalimide 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以65%的产率得到3,4-dimethoxyphthalimide
  参考文献：
  名称：

  A novel synthetic approach to isoindolobenzazepine alkaloid, chilenine, employing SmI2-mediated pinacolic coupling reaction

  摘要：

  Samarium(II) diiodide-mediated intramolecular reductive coupling reaction of phthalimides with N-formylated alkyl side chains is shown to afford dihydroxylated tricyclic lactams with 5-7-membered rings. This process was further applied for the preparation of an isoindolobenzazepine alkaloid, chilenine, by featuring the elaboration of the functionalized phthalimide derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00881-x
• 作为产物：
  描述：

  3,4-dimethoxy-2-carbethoxybenzoic acid 、 4-甲氧基苄胺 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到N-(p-methoxybenzyl) 3,4-dimethoxyphthalimide
  参考文献：
  名称：

  A novel synthetic approach to isoindolobenzazepine alkaloid, chilenine, employing SmI2-mediated pinacolic coupling reaction

  摘要：

  Samarium(II) diiodide-mediated intramolecular reductive coupling reaction of phthalimides with N-formylated alkyl side chains is shown to afford dihydroxylated tricyclic lactams with 5-7-membered rings. This process was further applied for the preparation of an isoindolobenzazepine alkaloid, chilenine, by featuring the elaboration of the functionalized phthalimide derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00881-x

文献信息

• Novel Chemoselective Desulfurization of γ-Phenylthio-Substituted Aromatic Lactams: Application to the Synthesis of Isoindolobenzazepine Alkaloid, Lennoxamine
  作者：Hidemi Yoda、Takamasa Suzuki、Kunihiko Takabe

  DOI：10.1055/s-2006-956452

  日期：2006.12

  Treatment of a variety of γ-phenylthio-substituted aromatic lactams with lithium aluminum hydride in the presence of cuprous iodide led to novel chemoselective desulfurization reactions to afford the corresponding substituted aromatic lactams without giving the carbonyl-reduced and/or ring-opened products in extremely high yields. This process was further applied to the total synthesis of an isoindolobenzazepine alkaloid, lennoxamine, by featuring the elaboration of the functionalized phthalimide derivative.

  在碘化亚铜存在下，用氢化铝锂处理各种δ-苯硫基取代的芳香族内酰胺，可产生新的化学选择性脱硫反应，从而得到相应的取代芳香族内酰胺，且不产生羰基还原和/或开环产物，收率极高。这一工艺还被进一步应用于异吲哚苯并氮杂卓生物碱--伦诺沙明的全合成，其特点是可以制备功能化邻苯二甲酰亚胺衍生物。