3-benzoyl-2-(tert-butyl)-3-hydroxyisoindolin-1-one | 32853-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-2-(tert-butyl)-3-hydroxyisoindolin-1-one
• 英文别名: 3-Benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-3-hydroxy-1H-isoindol-1-one；3-benzoyl-2-tert-butyl-3-hydroxyisoindol-1-one
• CAS: 32853-42-2
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: KDAGNCWPLGEGAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-phenylethynyl)-N-tert-butylbenzamide 在 Oxone 、 四丁基溴化铵 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以49%的产率得到3-benzoyl-2-(tert-butyl)-3-hydroxyisoindolin-1-one
  参考文献：
  名称：

  Synthesis of 3-Hydroxyisoindolin-1-ones through 1,4-Dioxane-Mediated Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water

  摘要：

  In this work, 1,4-dioxane-mediated hydroxylhydrative aza-cyclization of 2-alkynylbenzamide is developed for the synthesis of 3-hydroxylisoindolin-1-ones. The transformation proceeds smoothly in water with good yields and a broad reaction scope. Mechanistic studies show that regioselective brimonative 5-exo-dig aza-cyclization, bromohydration of the resulting alkene groups, and hydrolysis of dibromo compounds are involved. Compared to the traditional methodologies, the synthetic procedure reported herein represents a cleaner route toward 3-hydroxylisoindolin-1-ones.

  DOI：

  10.1021/acs.joc.9b03466

文献信息

• VALTER, R. EH.;BATSE, A. EH.;VALTERE, S. P.;KAMPARE, R. B., IZV. AN LATVSSR. CEP. XIM., 1983, N 1, 111-115
  作者：VALTER, R. EH.、BATSE, A. EH.、VALTERE, S. P.、KAMPARE, R. B.

  DOI：——

  日期：——
• Synthesis of 3-Hydroxyisoindolin-1-ones through 1,4-Dioxane-Mediated Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water
  作者：Renzhi Liu、Min Yang、Wenlin Xie、Wenbi Dong、Hongwei Zhou、Sarita Yadav、Vladimir Ivanovich Potkin、Guanyinsheng Qiu

  DOI：10.1021/acs.joc.9b03466

  日期：2020.4.17

  In this work, 1,4-dioxane-mediated hydroxylhydrative aza-cyclization of 2-alkynylbenzamide is developed for the synthesis of 3-hydroxylisoindolin-1-ones. The transformation proceeds smoothly in water with good yields and a broad reaction scope. Mechanistic studies show that regioselective brimonative 5-exo-dig aza-cyclization, bromohydration of the resulting alkene groups, and hydrolysis of dibromo compounds are involved. Compared to the traditional methodologies, the synthetic procedure reported herein represents a cleaner route toward 3-hydroxylisoindolin-1-ones.