ethyl 2-cyano-2-(3,5,5-trimethyl-2-cyclohexenyliden)acetate | 78814-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 2-cyano-2-(3,5,5-trimethyl-2-cyclohexenyliden)acetate
• 英文别名: ethyl 2-cyano-2-(3,3,5-trimethylcyclohex-5-enylidene)acetate；(E)-ethyl 2-cyano-2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)acetate；3-(1-Ethoxycarbonyl-1-cyanmethylen)-1,5,5-trimethyl-cyclohexen；ethyl (2E)-2-cyano-2-(3,5,5-trimethylcyclohex-2-enylidene)acetate；cyano-(3,5,5-trimethyl-cyclohex-2-enyliden)-acetic acid ethyl ester；Cyan-(3,5,5-trimethyl-cyclohex-2-enyliden)-essigsaeure-aethylester；ethyl 2-cyano-2-(3,3,5-trimethylcy-clohexylidene)acetate；ethyl (2E)-2-cyano-2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)acetate
• CAS: 78814-23-0
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: SLTHCZSLXPGFLV-QXMHVHEDSA-N

物化性质

• 沸点：
  338.5±25.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-2-(3,5,5-trimethyl-2-cyclohexenyliden)acetate 在 哌啶 、 二正丁基氧化锡 作用下， 以 丙醇 、 甲苯 为溶剂， 反应 31.0h， 生成
  参考文献：
  名称：

  Synthesis and Nonlinear-Optical Properties of Vinyl-Addition Poly(norbornene)s

  摘要：

  Vinyl-addition poly(norbornene) copolymers functionalized with nonlinear optical chromophore side groups have been prepared using (eta(6)-toluene)Ni(C6F5)(2), and their electrooptic properties have been characterized. The nickel complex used to polymerize the norbornene monomers is tolerant to many functional groups found in nonlinear optical chromophores although nitriles and amines other than trisubstituted amines strongly inhibit the reaction. A vinyl-addition copolymer of hexylnorbornene and a norbornene-functionalized Disperse Red 1 chromophore was scaled up and studied in detail. Initial studies indicate that electric field poling is effective but that relaxation of polar order in the poly(norbornene) is faster than in a comparable methacrylate copolymer.

  DOI：

  10.1021/ma040044i
• 作为产物：
  描述：

  异佛尔酮 、 氰乙酸乙酯 在 ammonium acetate 、 溶剂黄146 作用下， 生成 ethyl 2-cyano-2-(3,5,5-trimethyl-2-cyclohexenyliden)acetate
  参考文献：
  名称：

  Engineering of highly efficient tetrahydroquinoline sensitizers for dye-sensitized solar cells

  摘要：

  Four novel tetrahydroquinoline dyes by inserting isophorone and/or thiophene moieties as pi bridge between the electron donating unit of substituted tetrahydroquinoline and the electron withdrawing unit of cyano carboxylic acid have been synthesized and successfully applied to dye-sensitized solar cells. Among them, DSCs sensitized by HYTIC, which shows the simplest molecular structure, exhibit improved efficiency of 7.0%. This by now is the highest efficiency for the reported tetrahydroquinoline sensitizers and comparable to the performance of N719-sensitized solar cells under the conditions employed here. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.004

文献信息

• Photophysical and thermal properties of novel solid state fluorescent benzoxazole based styryl dyes from a DFT study
  作者：Urmiladevi Narad Yadav、Haribhau Shantaram Kumbhar、Saurabh Satish Deshpande、Suban Kumar Sahoo、Ganapati Subray Shankarling

  DOI：10.1039/c4ra12908c

  日期：——

  excellent thermal and photochemical stability. The effect of the benzoxazole moiety on the photophysical properties is explained by comparing with reported analogues and density functional theory (DFT) calculations. Thus investigations of photophysical properties provide an important foundation for the molecular design and development of novel optoelectronic materials for OLED and NLO applications.

  新型苯并恶唑苯乙烯基染料6a-6e与供体（D）–π（pi）–受体（A）进行了合成和表征。研究了染料的光谱（吸收和发射）和热重特性。与它们报道的类似物相比，发现它们具有高摩尔消光系数的红移吸收。这些化合物在固态（540–603 nm）处显示出增强的荧光发射。它们表现出优异的热和光化学稳定性。通过与已报道的类似物和密度泛函理论（DFT）计算结果进行比较，可以解释苯并恶唑基团对光物理性质的影响。因此，光物理性质的研究为分子设计和开发用于OLED和NLO应用的新型光电材料提供了重要的基础。
• Le Baut; Sparfel; Clairc, European Journal of Medicinal Chemistry, 1983, vol. 18, # 5, p. 447 - 455
  作者：Le Baut、Sparfel、Clairc、et al.

  DOI：——

  日期：——
• Synthesis of Diphenylamine-Based Novel Fluorescent Styryl Colorants by Knoevenagel Condensation Using a Conventional Method, Biocatalyst, and Deep Eutectic Solvent
  作者：Yogesh A. Sonawane、Sunanda B. Phadtare、Bhushan N. Borse、Amit R. Jagtap、Ganapati S. Shankarling

  DOI：10.1021/ol902976u

  日期：2010.4.2

  Novel Y-shaped-acceptor-pi-donor-pi-acceptor-type compounds, synthesized from 4,4'-hexyliminobisbenzaldehyde as electron donors and different active methylene compounds as electron acceptors, were produced by conventional Knoevenagel condensation alone, with a deep eutectic solvent, or with a lipase biocatalyst to compare the yield and recyclability among the three methods. Yield, reaction time, reaction temperature, and recyclability were compared among the three methods. The photophysical properties and thermal stability of the products were also investigated.
• Photographic sensitizing dyes and emulsions containing them
  申请人：EASTMAN KODAK CO

  公开号：US02882158A1

  公开（公告）日：1959-04-14
• Assignment of stereochemistry to cyclohexenylidenecyanoacetates by1H NMR spectroscopy
  作者：Vassilios Bardakos、Constantine Sandris

  DOI：10.1002/mrc.1270150405

  日期：1981.4

  AbstractThe stereochemistry of various pairs of isomeric 2‐cyclohexen‐1‐ylidenecyanoacetates was assigned using 1H NMR spectroscopy. The isomers with the γ‐methylene or the γ‐vinyl protons cis to the carbalkoxy group were found to have the signals of these protons at approximately 0.3 ppm and 1 ppm, respectively, downfield relative to their geometrical isomers or the corresponding 2‐cyclohexen‐1‐ylidenemalononitriles. The observation regarding the γ‐vinyl proton proved useful for the assignment of configuration to cyclohex‐enylidenecyanoacetates derived form cholest‐4‐en‐3‐one. The large and constant downfield shift (c. 1 ppm) of the γ‐vinyl proton when cis to the ester group results from the rigid cyclohexenylidenecyanoacetate system, in which the vinylic proton can approach more closely to the magnetically anisotropic ester carbonyl group.