3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4,4-trifluoro-3-hydroxy-butyric acid | 934961-91-8

• 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-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4,4-trifluoro-3-hydroxy-butyric acid
• 英文别名: (r)-3-((1,3-Dioxoisoindolin-2-yl)methyl)-4,4,4-trifluoro-3-hydroxybutanoic acid；(3R)-3-[(1,3-dioxoisoindol-2-yl)methyl]-4,4,4-trifluoro-3-hydroxybutanoic acid
• CAS: 934961-91-8
• 化学式: C₁₃H₁₀F₃NO₅
• mdl: MFCD09702247
• 分子量: 317.221
• InChiKey: DWWWFCHWHXIPAH-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4,4-trifluoro-3-hydroxy-butyric acid 在 盐酸 、 溶剂黄146 作用下， 以90%的产率得到4,4,4-trifluoro-3-hydroxy-3-(aminomethyl)-butanoic acid
  参考文献：
  名称：

  Synthesis of optically active β-hydroxy-β-polyfluoromethyl GABAs

  摘要：

  A general synthetic route to polyfluoromethyl containing analogues of GABA-beta-hydroxy-beta-tri- and difluoromethyl GABAs 9a and 9b was developed, using the corresponding beta-alkoxyvinyl polyfluoromethyl ketones-enones 1a and 1b as starting materials. Both enantiomers of the potential biologically active compound 9a were obtained by chiral resolution with (R)- or (S)-phenylethylamine: (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.005
• 作为产物：
  描述：

  (E)-1,1,1-trifluoro-4-ethoxy-2-(aminomethyl)-3-buten-2-ol 在 吡啶 、 盐酸 、 jones' reagent 、 R(+)-alpha-甲基苄胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 89.0h， 生成 3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4,4-trifluoro-3-hydroxy-butyric acid
  参考文献：
  名称：

  Synthesis of optically active β-hydroxy-β-polyfluoromethyl GABAs

  摘要：

  A general synthetic route to polyfluoromethyl containing analogues of GABA-beta-hydroxy-beta-tri- and difluoromethyl GABAs 9a and 9b was developed, using the corresponding beta-alkoxyvinyl polyfluoromethyl ketones-enones 1a and 1b as starting materials. Both enantiomers of the potential biologically active compound 9a were obtained by chiral resolution with (R)- or (S)-phenylethylamine: (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.005

文献信息

• Synthesis of optically active β-hydroxy-β-polyfluoromethyl GABAs
  作者：Elena N. Shaitanova、Igor I. Gerus、Michael Yu. Belik、Valery P. Kukhar

  DOI：10.1016/j.tetasy.2007.01.005

  日期：2007.2

  A general synthetic route to polyfluoromethyl containing analogues of GABA-beta-hydroxy-beta-tri- and difluoromethyl GABAs 9a and 9b was developed, using the corresponding beta-alkoxyvinyl polyfluoromethyl ketones-enones 1a and 1b as starting materials. Both enantiomers of the potential biologically active compound 9a were obtained by chiral resolution with (R)- or (S)-phenylethylamine: (c) 2007 Elsevier Ltd. All rights reserved.