(+/-)-3-hydroxy-2-propionyl-isoindolin-1-one | 26268-94-0

• 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-hydroxy-2-propionyl-isoindolin-1-one
• 英文别名: 3-hydroxy-2-propionyl-2,3-dihydro-isoindol-1-one；3-hydroxy-2-propanoyl-3H-isoindol-1-one
• CAS: 26268-94-0
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: AYRRTQMNSDSDSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  145.5-146.5 °C
• 沸点：
  403.2±45.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸异丙烯酯 、 (+/-)-3-hydroxy-2-propionyl-isoindolin-1-one 在 Alcaligenes species lipase QL 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以100%的产率得到(1R)-3-oxo-2-propionyl-2,3-dihydro-1H-isoindol-1-yl acetate
  参考文献：
  名称：

  Lipase-catalyzed dynamic kinetic resolution of hemiaminals

  摘要：

  The enzymatic dynamic kinetic resolution of N-acylhemiaminals by various lipases, namely, lipase PS, lipase AK and lipase QL, has been investigated. The acetylation of racemic N-acylhemiaminals with lipases exclusively produced the (R)-enantiomers in enantiomerically pure form and quantitative yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00313-6
• 作为产物：
  描述：

  3-羟基异吲哚啉-1-酮 在 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 生成 (+/-)-3-hydroxy-2-propionyl-isoindolin-1-one
  参考文献：
  名称：

  Dynamic kinetic resolution of hemiaminals with axially chiral twisted amides

  摘要：

  Dynamic kinetic resolution of N-acylhemiaminals was performed by enantioselective acylation of the hydroxy groups with chiral twisted amides. The stereoselectivity was reversed in the presence of 4-DMAP. The absolute configuration of the products was determined based on the sign of CD Cotton effects. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00521-4

文献信息

• Dynamic kinetic resolution of hemiaminals using a novel DMAP catalyst
  作者：Shinji Yamada、Kaori Yamashita

  DOI：10.1016/j.tetlet.2007.11.026

  日期：2008.1

  We describe the first catalytic dynamic kinetic resolution of hemiaminals mediated by an organocatalyst. A 0.1-1 mol % catalyst loading is effective for the dynamic kinetic resolution of hemiaminals to produce esters up to 88% ee in high yields. A 10 mol % catalyst loading resulted in a decreased selectivity, whereas the selectivity increased at 50 degrees C. The absolute configuration is assigned on the basis of the empirical Cotton effect rule. (C) 2007 Elsevier Ltd. All rights reserved.
• Lipase-catalyzed dynamic kinetic resolution of hemiaminals
  作者：Mohd. Sharfuddin、Atsushi Narumi、Yuko Iwai、Keiko Miyazawa、Shinji Yamada、Toyoji Kakuchi、Harumi Kaga

  DOI：10.1016/s0957-4166(03)00313-6

  日期：2003.6

  The enzymatic dynamic kinetic resolution of N-acylhemiaminals by various lipases, namely, lipase PS, lipase AK and lipase QL, has been investigated. The acetylation of racemic N-acylhemiaminals with lipases exclusively produced the (R)-enantiomers in enantiomerically pure form and quantitative yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Dynamic kinetic resolution of hemiaminals with axially chiral twisted amides
  作者：Shinji Yamada、Emiko Noguchi

  DOI：10.1016/s0040-4039(01)00521-4

  日期：2001.5

  Dynamic kinetic resolution of N-acylhemiaminals was performed by enantioselective acylation of the hydroxy groups with chiral twisted amides. The stereoselectivity was reversed in the presence of 4-DMAP. The absolute configuration of the products was determined based on the sign of CD Cotton effects. (C) 2001 Elsevier Science Ltd. All rights reserved.