(E)-1,1,1-trifluoro-4-ethoxy-2-(aminomethyl)-3-buten-2-ol | 934961-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,1,1-trifluoro-4-ethoxy-2-(aminomethyl)-3-buten-2-ol
• 英文别名: 2-(Aminomethyl)-4-ethoxy-1,1,1-trifluorobut-3-en-2-ol；(E)-2-(aminomethyl)-4-ethoxy-1,1,1-trifluorobut-3-en-2-ol
• CAS: 934961-84-9
• 化学式: C₇H₁₂F₃NO₂
• mdl: MFCD09702254
• 分子量: 199.173
• InChiKey: UMACIHMNGIOELS-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-乙氧基-3-三氟甲基-1,3-丁二烯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 (E)-1,1,1-trifluoro-4-ethoxy-2-(aminomethyl)-3-buten-2-ol
  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

• A new synthetic route to 3-polyfluoroalkyl-containing pyrroles
  作者：Elena N. Shaitanova、Igor I. Gerus、Valery P. Kukhar

  DOI：10.1016/j.tetlet.2007.12.048

  日期：2008.2

  A novel approach to 3-polyfluoroalkyl pyrroles is reported based on step by step reactions: 1,2-addition of Me3SiCN to β-alkoxyvinyl polyfluoroalkyl ketones, reduction with LiAlH4 and subsequent hydrolysis with intramolecular cyclization. The hydrolytic instability of various polyfluoroalkyl groups at position 3 of the pyrrole ring was evident and a pathway for the hydrolysis was proposed.

  据报导一种基于逐步反应的3-多氟烷基吡咯的新颖方法：将Me 3 SiCN 1，2-加成至β-烷氧基乙烯基多氟烷基酮，用LiAlH 4还原并随后通过分子内环化进行水解。在吡咯环的3位上的各种多氟烷基的水解不稳定性是明显的，并提出了水解的途径。
• 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.