3-hydroxy-2-methylene-3-(4-trifluoromethylphenyl)propanenitrile | 220175-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-hydroxy-2-methylene-3-(4-trifluoromethylphenyl)propanenitrile
• 英文别名: 2-(Hydroxy(4-(trifluoromethyl)phenyl)methyl)acrylonitrile；2-[hydroxy-[4-(trifluoromethyl)phenyl]methyl]prop-2-enenitrile
• CAS: 220175-93-9
• 化学式: C₁₁H₈F₃NO
• mdl: MFCD11130363
• 分子量: 227.186
• InChiKey: VANVANNXAKFOOY-UHFFFAOYSA-N

物化性质

• 沸点：
  347.0±42.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-methylene-3-(4-trifluoromethylphenyl)propanenitrile 在 sodium nitrate 、 1-己基-3-甲基咪唑硫酸氢盐 作用下， 生成 (E)-2-formyl-3-[4-(trifluoromethyl)phenyl]prop-2-enenitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of new epalrestat analogues as aldose reductase inhibitors (ARIs)

  摘要：

  Baylis-Hillman chemistry derived four series of new epalrestat analogues were synthesized. Three structural changes are introduced in these 39 new epalrestat analogues synthesized. All compounds were evaluated for their in vitro aldose reductase inhibitory (ALR) activity. Biological activity data indicates that compounds 6, 16, 19, 28 and 29 are potent and the activity is in the range of reference drug, epalrestat. Molecular modelling studies were performed to understand the binding interactions of these active molecules with the ALR protein. Molecular docking data indicates the key interactions of epalrestat were retained in some of the active compounds whereas some new interactions were noticed for other molecules. The modifications introduced on epalrestat have impact for developing a new-type of ALR inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.043
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 丙烯腈 在 三乙烯二胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以78%的产率得到3-hydroxy-2-methylene-3-(4-trifluoromethylphenyl)propanenitrile
  参考文献：
  名称：

  水溶液-有机溶剂体系中的Morita-Baylis-Hillman反应

  摘要：

  我们发现，以不同的比例混合的水和有机溶剂可以使Morita-Baylis-Hillman反应的收率和反应时间短。本信详细介绍了我们在几种芳香醛与丙烯酸甲酯或丙烯腈之间的森田-贝利斯-希尔曼反应中的发现。与DBU，DMAP，HMT，咪唑和三乙胺相比，DABCO的催化剂选择也得到了最好的评价。

  DOI：

  10.1016/j.tetlet.2008.07.140

文献信息

• The Morita–Baylis–Hillman reaction in aqueous–organic solvent system
  作者：Rodrigo O.M.A. de Souza、Vera L.P. Pereira、Pierre M. Esteves、Mario L.A. A. Vasconcellos

  DOI：10.1016/j.tetlet.2008.07.140

  日期：2008.10

  mixed at different proportions can give good to excellent yields and short reaction times for the Morita–Baylis–Hillman reaction. The present Letter details our findings in the Morita–Baylis–Hillman reaction between several aromatic aldehydes and methyl acrylate or acrylonitrile. The selection of the catalyst was also evaluated and DABCO affored the best results when compared to DBU, DMAP, HMT, Imidazole

  我们发现，以不同的比例混合的水和有机溶剂可以使Morita-Baylis-Hillman反应的收率和反应时间短。本信详细介绍了我们在几种芳香醛与丙烯酸甲酯或丙烯腈之间的森田-贝利斯-希尔曼反应中的发现。与DBU，DMAP，HMT，咪唑和三乙胺相比，DABCO的催化剂选择也得到了最好的评价。
• Synthesis of 1,3-Dialkyl-1,2,3-triazolium Ionic Liquids and Their Applications to the Baylis−Hillman Reaction
  作者：Yunkyung Jeong、Jae-Sang Ryu

  DOI：10.1021/jo100618d

  日期：2010.6.18

  Novel 1,3-dialkyl-1,2,3-triazolium ionic liquids were synthesized via click reactions using 1-trimethylsilylacetylene and alkyl azides and were efficient reaction media for the Baylis−Hillman reaction. The problems associated with deprotonation of the C-2 hydrogen of [bmim][PF6] could be suppressed in the reaction of [bmTr][PF6] or [bmTr][NTf2]. 1,3-Dialkyl-1,2,3-triazolium ionic liquids are chemically

  新型的1,3-二烷基-1,2,3-三唑鎓离子液体是通过使用1-三甲基甲硅烷基乙炔和叠氮化物的点击反应合成的，是Baylis - Hillman反应的有效反应介质。在[bmTr] [PF 6 ]或[bmTr] [NTf 2 ]的反应中，可以抑制与[bmim] [PF 6 ]的C-2氢的去质子化有关的问题。1，3-二烷基-1，2，3-三唑鎓离子液体在碱性条件下是化学惰性的，并且比普通的1，3-二烷基咪唑鎓离子液体更适合于涉及碱的反应介质。
• A New and Efficient Method for the Isomerization of Secondary Functional Allylic Alcohols into their Primary Isomers
  作者：Imen Beltaïef、Souhaïra Hbaïeb、Rafaâ Besbes、Hassen Amri、Monique Villiéras、Jean Villiéras

  DOI：10.1055/s-1998-2220

  日期：1998.12
• High selective leishmanicidal activity of 3-hydroxy-2-methylene-3-(4-bromophenyl)propanenitrile and analogous compounds
  作者：R.O.M.A. de Souza、V.L.P. Pereira、M.F. Muzitano、C.A.B. Falcão、B. Rossi-Bergmann、E.B.A. Filho、M.L.A.A. Vasconcellos

  DOI：10.1016/j.ejmech.2006.07.013

  日期：2007.1

  Sixteen not new aromatic compounds were prepared by one-pot reaction i.e. through Baylis-Hillman reaction and were the first time evaluated against promastigote Leishmania amazonensis and infected mammalian cells. Most of the compounds were selectively more active against amastigotes than the reference drug sodium stibogluconate (Pentostam, IC50 = 44.7 mu M). We found that 3-hydroxy-2-methylene-3-(4-broinophenyl)propanenitrile (13) was the most active (IC50 = 12.5 mu M) and safer compound (0.0 (0.9); % macrophage LDH release), being the lead compound. (c) 2006 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of new epalrestat analogues as aldose reductase inhibitors (ARIs)
  作者：Thatikonda Narendar Reddy、Mettu Ravinder、Pankaj Bagul、Keerthi Ravikanti、Chandrakant Bagul、Jagadeesh Babu Nanubolu、Kolupula Srinivas、Sanjay K. Banerjee、Vaidya Jayathirtha Rao

  DOI：10.1016/j.ejmech.2013.10.043

  日期：2014.1

  Baylis-Hillman chemistry derived four series of new epalrestat analogues were synthesized. Three structural changes are introduced in these 39 new epalrestat analogues synthesized. All compounds were evaluated for their in vitro aldose reductase inhibitory (ALR) activity. Biological activity data indicates that compounds 6, 16, 19, 28 and 29 are potent and the activity is in the range of reference drug, epalrestat. Molecular modelling studies were performed to understand the binding interactions of these active molecules with the ALR protein. Molecular docking data indicates the key interactions of epalrestat were retained in some of the active compounds whereas some new interactions were noticed for other molecules. The modifications introduced on epalrestat have impact for developing a new-type of ALR inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.