2-(3-trimethylsilylprop-2-ynylidene)malononitrile | 69656-67-3

• 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: 2-(3-trimethylsilylprop-2-ynylidene)malononitrile
• 英文别名: <3-(Trimethylsilyl)-2-propinyliden>-malononitril；[3-(trimethylsilyl)prop-2-yn-1-ylidene]propanedinitrile；[3-(Trimethylsilyl)prop-2-yn-1-ylidene]propane dinitrile；2-(3-trimethylsilylprop-2-ynylidene)propanedinitrile
• CAS: 69656-67-3
• 化学式: C₉H₁₀N₂Si
• 分子量: 174.277
• InChiKey: FBEVDCDCKCXHTA-UHFFFAOYSA-N

物化性质

• 沸点：
  74 °C(Press: 1 Torr)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-trimethylsilylprop-2-ynylidene)malononitrile 在 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 2-Prop-2-ynylidenepropanedinitrile
  参考文献：
  名称：

  1,2,3-Triazoles as Conjugative π-Linkers in Push−Pull Chromophores: Importance of Substituent Positioning on Intramolecular Charge-Transfer

  摘要：

  Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from lambda(max) = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.

  DOI：

  10.1021/ol801253z
• 作为产物：
  描述：

  3-三甲基甲硅烷基丙炔醛 以73%的产率得到
  参考文献：
  名称：

  BORISOVA A. I.; VYAZANKIN N. S.; MEDVEDEVA A. S.; KALIXMAN I. D., ZH. OBSHCH. XIMII, 1978, 48, HO 12, 2800

  摘要：

  DOI：

文献信息

• New donor–acceptor chromophores by formal [2+2] cycloaddition of donor-substituted alkynes to dicyanovinyl derivatives
  作者：Peter D. Jarowski、Yi-Lin Wu、Corinne Boudon、Jean-Paul Gisselbrecht、Maurice Gross、W. Bernd Schweizer、François Diederich

  DOI：10.1039/b821230a

  日期：——

  around 40° from X-ray analysis, but retain strong quinoidal character. The mechanism of this reaction has been studied computational using density functional methods in the gas-phase and using the polarizable continuum model (PCM) for addressing solvent effects. The complete reaction free-energy profile has been determined for the reaction of 1,1-dicyanoethene and 4-ethynyl-N,N-dimethylaniline. The

  富电子炔烃与环烷烃之间环加成反应的有效方法 四氰基乙烯 （东北电力公司） 或者 7,7,8,8-四氰基喹二甲烷 （全国质量监督检验检疫总局），然后进行逆电环化，扩展到 双氰基乙烯基 产生新的供体-受体推挽的衍生物 1,1-二氰基丁二烯基发色团具有优异的定量收率（63–98％），表现出300至600 nm的强电荷转移（CT）吸收。通过改变亲核和亲电子组分来确定该反应的范围。电化学研究表明，这些系统的CT特性很容易通过亲电试剂的取代进行调节，这对最低的未占据分子轨道（LUMO）的影响最大。不可逆的还原电势范围约为。在CH 2 Cl 2中相对于铁/二茂铁对（-1.2至-1.9 VFc +/Fc）的测量依据是循环伏安法（CV）和旋转盘伏安法（RDV）。发色团显示N，N-二甲基苯胺基供体和1,1-二氰基乙烯基受体部分之间存在显着的非平面性，X射线分析得出的扭转角约为40°，但保留了强的喹诺酮性质。已
• β-Cyclodextrin-catalyzed three-component synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles from propynals, trimethylsilyl azide and malononitrile in water
  作者：Alevtina S. Medvedeva、Maria M. Demina、Tran D. Vu、Mikhail V. Andreev、Nina S. Shaglaeva、Lyudmila I. Larina

  DOI：10.1016/j.mencom.2016.07.020

  日期：2016.7

  An efficient green method for the selective synthesis of new 4,5-disubstituted 1H-1,2,3-triazoloalkylidenes via the beta-cyclodextrin-catalyzed three-component reaction between substituted propynals, trimethylsilyl azide and malononitrile in water at room temperature has been developed.
• Microwave-assisted dry oxidation of 3-trialkylsilyl(germyl)prop-2-yn-1-ols to propynals and the direct conversion of acetylenic alcohols to ynimines and enynes
  作者：Alexander V. Mareev、Alevtina S. Medvedeva、Alexander V. Khatashkeev、Andrey V. Afonin

  DOI：10.1070/mc2005v015n06abeh002008

  日期：2005.1

  The efficient solvent-free microwave-assisted oxidation of 3-trialkylsilyl(germyl)prop-2-yn-1-ols with manganese dioxide or pyridinium chlorochromate to propynals and the direct conversion of acetylenic alcohols to the corresponding imines and Knovenagel adducts have been carried out.
• Hopf, Henning; Kreutzer, Martin, Angewandte Chemie, 1990, vol. 102, # 4, p. 425 - 426
  作者：Hopf, Henning、Kreutzer, Martin

  DOI：——

  日期：——
• Borisova,A.I. et al., Journal of general chemistry of the USSR, 1978, vol. 48, p. 2540
  作者：Borisova,A.I. et al.

  DOI：——

  日期：——