N-(2-allyl-3-oxoisoindolin-1-yl)-4-methylbenzenesulfonamide | 1361321-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-allyl-3-oxoisoindolin-1-yl)-4-methylbenzenesulfonamide
• 英文别名: 4-methyl-N-(3-oxo-2-prop-2-enyl-1H-isoindol-1-yl)benzenesulfonamide
• CAS: 1361321-13-2
• 化学式: C₁₈H₁₈N₂O₃S
• 分子量: 342.419
• InChiKey: MOMNQCCJFZLDSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-烯丙基邻苯二甲酰亚胺 在 甲醇 、 sodium tetrahydroborate 、 C₁₀H₁₉Cl₈IrO₂Sn₃ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 N-(2-allyl-3-oxoisoindolin-1-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  N-酰基亚胺离子化学中的多金属铱锡（Ir-Sn 3）催化剂：通过分子内和分子间酰胺基烷基化反应合成3-取代的异吲哚满酮

  摘要：

  AbstractThe multimetallic iridium‐tritin (Ir‐Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O)2}] (1) proved to be a highly effective catalyst towards COH bond activation of γ‐hydroxylactams, leading to a nucleophilic substitution reaction known as the α‐amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3‐dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3‐substituted isoindolinones and 5‐substituted pyrrolidin‐2‐ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir‐Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ‐hydroxylactam towards the formation of the N‐acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.magnified image

  DOI：

  10.1002/adsc.201400234

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.
• Multimetallic Iridium-Tin (Ir-Sn₃) Catalyst in<i>N</i>-Acyliminium Ion Chemistry: Synthesis of 3-Substituted Isoindolinones<i>via</i>Intra- and Intermolecular Amidoalkylation Reaction
  作者：Arnab Kumar Maity、Sujit Roy

  DOI：10.1002/adsc.201400234

  日期：2014.8.11

  AbstractThe multimetallic iridium‐tritin (Ir‐Sn3) complex [Cp*Ir(SnCl3)2SnCl2(H2O)2}] (1) proved to be a highly effective catalyst towards COH bond activation of γ‐hydroxylactams, leading to a nucleophilic substitution reaction known as the α‐amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer [Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3‐dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3‐substituted isoindolinones and 5‐substituted pyrrolidin‐2‐ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir‐Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ‐hydroxylactam towards the formation of the N‐acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.magnified image