3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4-difluoro-3-hydroxy-butyraldehyde | 934961-88-3

• 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-difluoro-3-hydroxy-butyraldehyde
• CAS: 934961-88-3
• 化学式: C₁₃H₁₁F₂NO₄
• 分子量: 283.231
• InChiKey: CXASOVDPDMBEBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.68
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4-difluoro-3-hydroxy-butyraldehyde 在 盐酸 、 jones' reagent 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 4,4-difluoro-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)-2-difluoromethyl-4-ethoxy-2-trimethylsilyloxy-3-butenenitrile 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 48.0h， 生成 3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,4-difluoro-3-hydroxy-butyraldehyde
  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 enantiomerically pure 4-polyfluoromethyl-4-hydroxy-homoprolines by intramolecular cyclization of 6-amino-5-polyfluoromethyl-hex-2-enoic acids
  作者：Elena N. Shaitanova、Igor I. Gerus、Valery P. Kukhar、Günter Haufe

  DOI：10.1016/j.jfluchem.2014.01.001

  日期：2014.4

  An effective route to racemic and enantiopure 4-polyfluoromethyl-4-hydroxy-homoprolines was developed based on readily available 2-alkoxyvinyl-polyfluoromethyl ketones. Key step of the synthesis was a diastereoselective heterocyclization of 6-amino-5-polyfluoromethyl-hex-2-enoic acids under acidic conditions. The absolute configuration of the stereogenic centers was determined by X-ray. (C) 2014 Elsevier B.V. All rights reserved.