ethyl tricyanoethylenecarboxylate | 153814-39-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl tricyanoethylenecarboxylate
• 英文别名: ethyl 2,3,3-tricyanoacrylate；Ethyl 2,3,3-tricyanoprop-2-enoate
• CAS: 153814-39-2
• 化学式: C₈H₅N₃O₂
• 分子量: 175.147
• InChiKey: JBWPEEPKXXZHNX-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  290.3±40.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(pentamethylcyclopentadienyl)iron(II) 、 ethyl tricyanoethylenecarboxylate 以 二氯甲烷 为溶剂， 以70%的产率得到decamethylferrocenium ethyl tricyanoethylenecarboxylate
  参考文献：
  名称：

  Synthesis, structure and magnetic characterization of decamethylmetallocenium ethyl tricyanoethylenecarboxylate charge-transfer salts

  摘要：

  Ethyl tricyanoethylenecarboxylate (ETCE) is a one-electron acceptor related to tetracyanoethylene that can serve as a building block for the construction of molecule-based magnets. The reactions of ETCE with decamethylmetallocenes, MCp2* (M = Cr, Mn, Fe) give three new charge-transfer salt magnets, [CrCp2*][ETCE] 1, [MnCp2*][ETCE] 2 and [FeCp2*][ETCE] 3. The expected mixed pi stacking of anions and cations is obtained, with the ETCE radical anion exhibiting typical disorder over two nearly equivalent footprints. Powder diffraction supports the belief that all three compounds are isomorphous. Magnetic measurements indicate that 1 is a soft ferromagnet, ordering below a critical temperature, T-c, of 3.8 K. Compound 2 exhibits complex magnetic behavior consisting of two frequency-dependent peaks in the ac susceptibility, the first at about 11.2 K and the second at about 7 K. At 1.8 K, the compound is hysteretic and exhibits a coercive field of 10 kG. Compound 3 is a glassy, apparently canted, ferromagnet displaying an out-of-phase ac susceptibility signal below about 3 K. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2008.10.032
• 作为产物：
  描述：

  四氰基乙烯 、 氰乙酸乙酯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以12%的产率得到ethyl tricyanoethylenecarboxylate
  参考文献：
  名称：

  用于环加成-逆电环化 (CA-RE) 和相关反应的酯取代的贫电子烯烃

  摘要：

  我们报告了由羧酸酯和氰基四取代的缺电子烯烃与富电子（二甲氨基）苯基取代的炔烃的反应。单酯或二酯取代的烯烃仅经历 [2+2] 环加成 - 逆电环化 (CA-RE) 反应，这对于多氰化乙烯来说已经很好建立，而三酯和四酯取代的烯烃也经历 [4+2] 杂-Diels –Alder (HDA) 反应与形成第三个产物，推测是通过 [3+2] 环加成反应，然后重排。电化学研究揭示了从 CA-RE 反应中获得的丁-1,3-二烯的第一还原电位的阴极位移，因为氰基取代了酯部分。通过酯交换、重氮化学对酯取代的 1,3-二烯进行后 CA-RE 功能化，并描述了交叉耦合。药理学上有趣的吡唑并吡喃的形成说明了酯取代的 CA-RE 产品的合成效用。

  DOI：

  10.1002/ejoc.201501085

文献信息

• Ester-Substituted Electron-Poor Alkenes for Cycloaddition-Retroelectrocyclization (CA-RE) and Related Reactions
  作者：Tristan A. Reekie、Etienne J. Donckele、Laurent Ruhlmann、Corinne Boudon、Nils Trapp、François Diederich

  DOI：10.1002/ejoc.201501085

  日期：2015.11

  the reactions of electron-deficient alkenes, tetrasubstituted by carboxylic ester and cyano groups, with electron-rich (dimethylamino)phenyl-substituted alkynes. Mono- or diester-substituted alkenes exclusively undergo the [2+2] cycloaddition–retroelectrocyclization (CA–RE) reaction, well established for multicyanated ethenes, whereas tri- and tetraester-substituted alkenes also undergo a [4+2] hetero-Diels–Alder

  我们报告了由羧酸酯和氰基四取代的缺电子烯烃与富电子（二甲氨基）苯基取代的炔烃的反应。单酯或二酯取代的烯烃仅经历 [2+2] 环加成 - 逆电环化 (CA-RE) 反应，这对于多氰化乙烯来说已经很好建立，而三酯和四酯取代的烯烃也经历 [4+2] 杂-Diels –Alder (HDA) 反应与形成第三个产物，推测是通过 [3+2] 环加成反应，然后重排。电化学研究揭示了从 CA-RE 反应中获得的丁-1,3-二烯的第一还原电位的阴极位移，因为氰基取代了酯部分。通过酯交换、重氮化学对酯取代的 1,3-二烯进行后 CA-RE 功能化，并描述了交叉耦合。药理学上有趣的吡唑并吡喃的形成说明了酯取代的 CA-RE 产品的合成效用。
• Room Temperature Dynamic Polymers Based on Diels-Alder Chemistry
  作者：P. Reutenauer、E. Buhler、P. J. Boul、S. J. Candau、J.-M. Lehn

  DOI：10.1002/chem.200802145

  日期：2009.2.9

  Polymer, heal thyself! Dynamic polymers formed by a reversible Diels–Alder reaction were formed and studied by using neutron scattering at room temperature. They were used to obtain thin films that displayed self‐healing at room temperature (see figure).

  聚合物，治愈自己！由可逆的狄尔斯-阿尔德反应形成的动态聚合物是通过在室温下使用中子散射来形成和研究的。它们被用来获得在室温下表现出自愈性的薄膜（见图）。
• Novel Catalytic Metathesis of Substituted Olefins Promoted by Rhenium(I) Enolate Complexes
  作者：Masafumi Hirano、Miwa Hirai、Yuji Ito、Atsushi Fukuoka、Sanshiro Komiya

  DOI：10.1246/cl.1994.165

  日期：1994.1

  Rhenium(I) enolate complexes Re(NCCHCO2Et)[NC(EtO2C)C=CHPh](PMe2Ph)4 and Re(NCCHCO2Et)(NCCH2CO2Et)(PMe2Ph)4 are found to catalyze unique olefin metathesis reaction of tetracyanoethylene with ethyl α-cyanocinnamate to give 1,1 dicyano-2-phenylethylene and ethyl 2,3,3-tricyanopropenoate at room temperature.

  铼（I）烯醇络合物Re（NCCHCO2Et）[NC（EtO2C）C=CHPh]（PMe2Ph）4和Re（NCCHCO2Et）（NCCH2CO2Et）（PMe2Ph）4被发现可在室温下催化四氰基乙烯与乙基α-氰基肉桂酸酯的独特烯烃复分解反应，生成1,1-二氰基-2-苯乙烯和乙基2,3,3-三氰基丙烯酸酯。
• Reversible Diels−Alder Reactions for the Generation of Dynamic Combinatorial Libraries
  作者：Peter J. Boul、Philippe Reutenauer、Jean-Marie Lehn

  DOI：10.1021/ol048065k

  日期：2005.1.1

  Condensation reactions between various dienes and dienophiles have been screened for reversibility. Functionalized fulvenes, bearing in particular biological groups, and cyanolefins have been found to react rapidly and reversibly, in the temperature range from -10 to +50 degreesC. These results pave the way for the development of dynamic combinatorial libraries based on reversible Diels-Alder chemistry.
• Dulog, Lothar; Koerner, Bernd; Heinze, Juergen, Liebigs Annalen, 1995, # 9, p. 1663 - 1672
  作者：Dulog, Lothar、Koerner, Bernd、Heinze, Juergen、Yang, Jianjun

  DOI：——

  日期：——