(E)-2-trifluoromethyl-4-ethoxy-2-trimethylsilyloxy-3-butenenitrile | 244074-91-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-2-trifluoromethyl-4-ethoxy-2-trimethylsilyloxy-3-butenenitrile
• 英文别名: E-4-ethoxy-2-trifluoromethyl-2-trimethylsilyloxybut-3-enenitrile；(E)-4-ethoxy-2-(trifluoromethyl)-2-((trimethylsilyl)oxy)but-3-enenitrile；(E)-4-ethoxy-2-(trifluoromethyl)-2-trimethylsilyloxybut-3-enenitrile
• CAS: 244074-91-7
• 化学式: C₁₀H₁₆F₃NO₂Si
• 分子量: 267.323
• InChiKey: ZLRCLCKLPGWFAY-VOTSOKGWSA-N

物化性质

• 沸点：
  84-85 °C(Press: 15 Torr)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2-trifluoromethyl-4-ethoxy-2-trimethylsilyloxy-3-butenenitrile 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 jones' reagent 作用下， 以 乙醚 、 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：

  三甲基氰硅烷 、 1-乙氧基-3-三氟甲基-1,3-丁二烯 在 三乙胺 作用下， 反应 12.0h， 以80%的产率得到(E)-2-trifluoromethyl-4-ethoxy-2-trimethylsilyloxy-3-butenenitrile
  参考文献：
  名称：

  合成含3-多氟烷基吡咯的新途径

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2007.12.048

文献信息

• Regioselective Addition of Trimethylsilyl Cyanide to β-Alkoxyvinyl Alkyl Ketones
  作者：Igor S. Kruchok、Igor I. Gerus、Valery P. Kukhar

  DOI：10.1016/s0040-4020(00)00603-7

  日期：2000.8

  The 1,2- and 1,4-addition reactions of trimethylsilyl cyanide to alkyl vinyl ketones were studied. Regioselectivity of this reaction depends on the structure of alkyl vinyl ketones, the reaction temperature and the nature of catalyst. The presence of alkoxy group in beta-position of alpha,beta-enone is the important condition for realization of 1,4-addition. Ambient temperature (25 degrees C) or base catalyst (NEt3) directed the reaction predominantly into 1,2-addition; higher temperature, electrophilic catalyst (I-2) and bulky alkyl substituents near the carbonyl group directed the reaction in 1,4-addition route. Hydrolysis of 1,4-adducts yields saturated fluorine-containing ketones containing CN- and ethoxy groups at the beta-position. (C) 2000 Published by Elsevier Science Ltd.
• Regioselective addition of trimethylsilyl cyanide toE-1,1,1-trifluoro-4-ethoxybut-3-en-2-one
  作者：Igor I. Gerus、Igor S. Kruchok、Valery P. Kukhar

  DOI：10.1016/s0040-4039(99)01174-0

  日期：1999.8

  The 1,2- and 1,4-addition reactions of trimethylsilyl cyanide to 1,1,1-trifluoro-4-ethoxybut-3-en-2-one were studied. The regioselectivity of this reaction depends on the temperature, the nature of solvent and the catalyst. low temperatures or basic catalysts direct in favour of 1,2-addition while high temperatures or acidic catalysts direct in favour of 1,4-addition. (C) 1999 Elsevier Science Ltd. All rights reserved.