1-羟基-3-氧代-2H-异吲哚-1-羧酸乙酯 | 67213-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-羟基-3-氧代-2H-异吲哚-1-羧酸乙酯
• 英文名称: 3-ethyoxycarbonyl-3-hydroxyisoindolin-1-one
• 英文别名: 3-ethoxycarbonyl-3-hydroxyisoindolin-1-one；1-Hydroxy-3-oxoisoindolin-1-carbonsaeure-ethylester；1-hydroxy-3-oxo-1,3-dihydro-isoindole-1-carboxylic acid ethyl ester；Ethyl 1-hydroxy-3-oxoisoindoline-1-carboxylate；ethyl 1-hydroxy-3-oxo-2H-isoindole-1-carboxylate
• CAS: 67213-78-9
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: ZXQNKISONGAFGH-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C(Solv: ethanol (64-17-5))
• 沸点：
  458.4±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-羟基-3-氧代-2H-异吲哚-1-羧酸乙酯 在 palladium on carbon 、 camphor-10-sulfonic acid 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  (±)-CSA catalyzed one-pot synthesis of 6,7-dihydrospiro[indole-3,1′-isoindoline]-2,3′,4(1H,5H)-trione derivatives: easy access of spirooxindoles and ibophyllidine-like alkaloids

  摘要：

  The domino dehydration/condensation/cyclization sequence reaction of cyclic enaminones with 3-hydroxy-3-ethoxycarbonylisoindolin-1-one derivatives has been successfully realized for the first time in toluene at 90 C by using a catalytic amount of commercially available inexpensive (+/-)-CSA (30 mol %). Gratifyingly, this novel domino protocol provides good to excellent yields of previously unknown class of 1-aryl/alkyl-substituted 6,7-dihydrospiro[indole-3,1 '-isoindoline]-2,3,4(111,5H)-trione derivatives. Moreover, biologically attractive spirooxindoles and ibophyllidine-like alkaloids have been prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.154
• 作为产物：
  描述：

  异喹啉-1,3,4-三酮 、 三乙胺 以68%的产率得到
  参考文献：
  名称：

  PETERSEN S.; HEITZER H., J. LIEBIGS ANN. CHEM., 1978, NO 2, 283-288

  摘要：

  DOI：

文献信息

• Ogata; Matsumoto; Tawara, European Journal of Medicinal Chemistry, 1981, vol. 16, # 4, p. 373 - 378
  作者：Ogata、Matsumoto、Tawara

  DOI：——

  日期：——
• (±)-CSA catalyzed Friedel–Crafts alkylation of indoles with 3-ethoxycarbonyl-3-hydoxyisoindolin-1-one: an easy access of 3-ethoxycarbonyl-3-indolylisoindolin-1-ones bearing a quaternary α-amino acid moiety
  作者：Anvita Srivastava、Shivendra Singh、Sampak Samanta

  DOI：10.1016/j.tetlet.2013.01.010

  日期：2013.3

  For the first time, a very simple, efficient, mild, catalytic, and one-step procedure for the synthesis of a series of new 3-ethoxycarbonyl-3-indolylsubstituted-isoindol-1-one derivatives has been achieved via a Friedel-Crafts alkylation of indoles with 3-hydroxy-3-ethoxycarbonylisoindolin-1-one at room temperature using easily available inexpensive camphor-10-sulfonic acid as an organocatalyst. The current protocol provides good to excellent yields of the title compounds with high substrate scope. In addition, the desired product possesses a chiral quaternary carbon center at the 3-position on isoindolin-1-one ring which is flanked by indole moiety, amino and ester groups for further elaborations. (C) 2013 Elsevier Ltd. All rights reserved.
• (±)-CSA catalyzed one-pot synthesis of 6,7-dihydrospiro[indole-3,1′-isoindoline]-2,3′,4(1H,5H)-trione derivatives: easy access of spirooxindoles and ibophyllidine-like alkaloids
  作者：Anvita Srivastava、Shaikh M. Mobin、Sampak Samanta

  DOI：10.1016/j.tetlet.2014.01.154

  日期：2014.3

  The domino dehydration/condensation/cyclization sequence reaction of cyclic enaminones with 3-hydroxy-3-ethoxycarbonylisoindolin-1-one derivatives has been successfully realized for the first time in toluene at 90 C by using a catalytic amount of commercially available inexpensive (+/-)-CSA (30 mol %). Gratifyingly, this novel domino protocol provides good to excellent yields of previously unknown class of 1-aryl/alkyl-substituted 6,7-dihydrospiro[indole-3,1 '-isoindoline]-2,3,4(111,5H)-trione derivatives. Moreover, biologically attractive spirooxindoles and ibophyllidine-like alkaloids have been prepared. (C) 2014 Elsevier Ltd. All rights reserved.
• PETERSEN S.; HEITZER H., J. LIEBIGS ANN. CHEM., 1978, NO 2, 283-288
  作者：PETERSEN S.、 HEITZER H.

  DOI：——

  日期：——