3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4,4-trifluoro-3-hydroxy-butyric acid | 929975-14-4

• 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: 3-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-4,4,4-trifluoro-3-hydroxybutanoic acid；3-[(1,3-dioxoisoindol-2-yl)methyl]-4,4,4-trifluoro-3-hydroxybutanoic acid
• CAS: 929975-14-4
• 化学式: C₁₃H₁₀F₃NO₅
• mdl: MFCD09702256
• 分子量: 317.221
• InChiKey: DWWWFCHWHXIPAH-UHFFFAOYSA-N

物化性质

• 沸点：
  504.3±50.0 °C(Predicted)
• 密度：
  1.600±0.06 g/cm3(Predicted)

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， 生成 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 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 new fluorinated analogs of GABA, Pregabalin bioisosteres, and their effects on [3H]GABA uptake by rat brain nerve terminals
  作者：T. Borisova、N. Pozdnyakova、E. Shaitanova、I. Gerus、M. Dudarenko、R. Mironets、G. Haufe、V. Kukhar

  DOI：10.1016/j.bmc.2015.06.038

  日期：2015.8

  Fluorinated analogs of natural substances take an essential place in the design of new biologically active compounds. New fluorinated analogs of γ-aminobutyric acid, that is, β-polyfluoroalkyl-GABAs (FGABAs), were synthesized with substituents: β-CF3-β-OH (1), β-CF3 (2); β-CF2CF2H (3). FGABAs are bioisosteres of Pregabalin (Lyrica®, Pfizer’s blockbuster drug, β-i-Bu-GABA), and have lipophilicity close

  天然物质的氟化类似物在新的生物活性化合物的设计中占有重要地位。新氟化γ氨基丁酸，即，β-多氟烷-GABAs（FGABAs），用取代基合成的类似物：β-CF 3 -β-OH（1），β-​​CF 3（2）; β-CF 2 CF 2 H（3）。FGABAs是普瑞巴林（Pyrizer的重磅炸弹药，β- i -Bu-GABA）的普瑞巴林的生物等排体，并且具有接近该药物的亲脂性。评估了合成的FGABA对离体大鼠脑神经末梢（突触体）摄取[ 3 H] GABA的影响，并将其与普瑞巴林的影响进行了比较。FGABA 1– 3（100μM）急性施用时不影响[ 3 H] GABA吸收的初始速度，而将FGABAs与突触小体初步孵育后发现该参数增加。在与突触体初步温育后，普瑞巴林引起[ 3 H] GABA吸收初始速度的单向变化。使用GAT1和GAT3，NO-711和SNAP5114分别FGABAs的能力的特异性抑制剂1
• 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.