3-acetoxy-1,3-dihydro-2-(2,4,6-trimethylphenyl)isoindol-1-one | 1332980-73-0

• 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: 3-acetoxy-1,3-dihydro-2-(2,4,6-trimethylphenyl)isoindol-1-one
• CAS: 1332980-73-0
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: YAWALKHRTYGZCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-acetoxy-1,3-dihydro-2-(2,4,6-trimethylphenyl)isoindol-1-one 、 烯丙基三甲基硅烷 在 三甲基氯硅烷 、 1,3-bis(2,4,6-trimethylphenyl)-2-iodoimidazolium triflate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以76%的产率得到
  参考文献：
  名称：

  Halogen-Bond-Catalyzed Addition of Carbon-Based Nucleophiles to N-Acylimminium Ions

  摘要：

  N-acylimminium ions are an important class of synthetic intermediates to produce diverse products upon treatment with different nucleophiles. Most of the reported catalytic protocol involved moisture-sensitive Lewis acids or transition metal. Herein, we reported an organocatalytic version by using halogen-bond catalyst as mild Lewis acid through anion-abstraction strategy. A preliminary result of enantioselective version by employing a chiral BINOL-phosphate anion has also been demonstrated.

  DOI：

  10.1021/acs.orglett.9b02006
• 作为产物：
  描述：

  1-(N-phthalimido)-2,4,6-trimethylbenzene 、 乙酸酐 在 三乙基硼氢化锂 作用下， 以1.25 g的产率得到3-acetoxy-1,3-dihydro-2-(2,4,6-trimethylphenyl)isoindol-1-one
  参考文献：
  名称：

  Halogen-Bond-Catalyzed Addition of Carbon-Based Nucleophiles to N-Acylimminium Ions

  摘要：

  N-acylimminium ions are an important class of synthetic intermediates to produce diverse products upon treatment with different nucleophiles. Most of the reported catalytic protocol involved moisture-sensitive Lewis acids or transition metal. Herein, we reported an organocatalytic version by using halogen-bond catalyst as mild Lewis acid through anion-abstraction strategy. A preliminary result of enantioselective version by employing a chiral BINOL-phosphate anion has also been demonstrated.

  DOI：

  10.1021/acs.orglett.9b02006

文献信息

• 2-Aminothiophene derivatives in a novel synthesis of phthalimidines
  作者：L. Yu. Ukhin、E. N. Shepelenko、L. V. Belousova、Zh. I. Orlova、G. S. Borodkin、K. Yu. Suponitsky

  DOI：10.1007/s11172-011-0057-3

  日期：2011.2

  New aminophthalides were synthesized from o-formylbenzoic acid and substituted 2-aminothiophenes. Two of these compounds underwent recyclization in boiling Ac2O to give the previously unknown 3-acetoxy-2-(3-cyano-4,5-dimethylthiophen-2-yl)-1,3-dihydroisoindol-1-one and 3-acetoxy-2-(3-cyano-4,5-tetramethylenethiophen-2-yl)-1,3-dihydroisoindol-1-one. The possible reaction mechanism and factors preventing the recyclization, in particular, the formation of intramolecular hydrogen bonds in the starting phthalides, were discussed. Some reactions of the resulting compounds with C-nucleophiles in trifluoroacetic acid were investigated. Two derivatives containing 4-hydroxy-3,5-di-tert-butylphenyl substituents were studied by X-ray diffraction.

  新型氨基酞类化合物由邻甲酰基苯甲酸和取代的2-氨基噻吩合成获得。其中两种化合物在沸腾的醋酸酐中发生环化反应，生成先前未知的3-乙酰氧基-2-(3-氰基-4,5-二甲基噻吩-2-基)-1,3-二氢异吲哚-1-酮和3-乙酰氧基-2-(3-氰基-4,5-四亚甲基噻吩-2-基)-1,3-二氢异吲哚-1-酮。讨论了可能的反应机理及阻止环化的因素，特别是起始酞类化合物中分子内氢键的形成。研究了所得化合物与三氟乙酸中的C-亲核试剂的一些反应。通过X射线衍射研究了两种含有4-羟基-3,5-二叔丁基苯基取代基的衍生物。