10b-phenyl-1,10b-dihydropyrido[2,1-a]isoindol-6(4H)-one | 1361321-22-3

• 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: 10b-phenyl-1,10b-dihydropyrido[2,1-a]isoindol-6(4H)-one
• 英文别名: 10b-Phenyl-1,4-dihydropyrido[2,1-a]isoindol-6-one
• CAS: 1361321-22-3
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: SNNGPACGLXNJGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10b-phenyl-1,10b-dihydropyrido[2,1-a]isoindol-6(4H)-one 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以96%的产率得到1,2,3,10b-tetrahydropyrido<2,1-a>isoindol-6(2H)-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
• 作为产物：
  描述：

  2,3-diallyl-3-phenylisoindolin-1-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到10b-phenyl-1,10b-dihydropyrido[2,1-a]isoindol-6(4H)-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

• Functionalisation of isoindolinones <i>via</i> a calcium catalysed Hosomi–Sakurai allylation
  作者：Ashley J. Basson、Mark G. McLaughlin

  DOI：10.1039/c9cc02450f

  日期：——

  A rapid and functionally tolerant calcium catalysed Hosomi–Sakurai reaction has been realised.

  已实现了一种快速且功能耐受的钙催化的细岛-榊井反应。