2-benzyl-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)isoindolin-1-one | 1361321-09-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-benzyl-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)isoindolin-1-one
• 英文别名: 2-benzyl-3-(4-hydroxy-2-oxochromen-3-yl)-3H-isoindol-1-one
• CAS: 1361321-09-6
• 化学式: C₂₄H₁₇NO₄
• 分子量: 383.403
• InChiKey: MPXBGGNWEQMKPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 2-benzyl-3-hydroxy-2,3-dihydro-isoindol-1-one 在 [Cp*Ir(SnCl₃)2{SnCl₂(H₂O)2}]*3H₂O 作用下， 以 1,2-二氯乙烷 为溶剂， 以96%的产率得到2-benzyl-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)isoindolin-1-one
  参考文献：
  名称：

  A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

  摘要：

  A multimetallic piano-stool complex [Cp*Ir-(SnCl3)(2){SnCl2(H2O)(2)}] (1) having Ir-Sn-3 motif has been synthesized from [Cp*IrCl2](2) and SnCl2. The multimetallic complex catalytically promotes the nucleophilic substitution reaction (here after alpha-amidoalkylation reaction) of gamma-hydroxylactams generated from phthalimidals to obtain decorated isoindolinones in excellent yields. Succinamidals, however, lead to the substituted pyrrolidinones (thermodynamic control product) via S(N)1-type path as well as eliminated pyrrolinones (kinetic control product) via an E1-type path, depending on the reaction parameters. A straightforward application of this methodology is to synthesize benzo-fused indolizidine alkaloid mimics.

  DOI：

  10.1021/jo202359e

文献信息

• A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through <i>N</i>-Acyliminium Ions
  作者：Arnab Kumar Maity、Sujit Roy

  DOI：10.1021/jo202359e

  日期：2012.3.16

  A multimetallic piano-stool complex [Cp*Ir-(SnCl3)(2)SnCl2(H2O)(2)}] (1) having Ir-Sn-3 motif has been synthesized from [Cp*IrCl2](2) and SnCl2. The multimetallic complex catalytically promotes the nucleophilic substitution reaction (here after alpha-amidoalkylation reaction) of gamma-hydroxylactams generated from phthalimidals to obtain decorated isoindolinones in excellent yields. Succinamidals, however, lead to the substituted pyrrolidinones (thermodynamic control product) via S(N)1-type path as well as eliminated pyrrolinones (kinetic control product) via an E1-type path, depending on the reaction parameters. A straightforward application of this methodology is to synthesize benzo-fused indolizidine alkaloid mimics.