(Z)-ethyl 2-cyano-2-(3, 5, 5-trimethylcyclohex-2-en-1-ylidene)acetate | 78814-24-1

• 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: (Z)-ethyl 2-cyano-2-(3, 5, 5-trimethylcyclohex-2-en-1-ylidene)acetate
• 英文别名: ethyl (2Z)-2-cyano-2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)acetate
• CAS: 78814-24-1
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: SLTHCZSLXPGFLV-VAWYXSNFSA-N

物化性质

• 沸点：
  160 °C(Press: 0.1 Torr)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 2-cyano-2-(3, 5, 5-trimethylcyclohex-2-en-1-ylidene)acetate 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 (Z)-ethyl 2-cyano-2-(3-((E)-4-((4-((E)-2-(4-(dicyanomethylene)-6-methyl-4H-pyran-2-yl)vinyl)phenyl)(phenyl)amino)styryl)-5,5-dimethylcyclohex-2-en-1-ylidene)acetate
  参考文献：
  名称：

  Four asymmetric bis-branched triphenylamine derivatives with charge transfer from one branch to the other: Two-photon emissions and bio-imaging applications

  摘要：

  Four asymmetric bis-branched triphenylamine-cored compounds with different electron-withdrawing groups have been synthesized and their optical properties have been systematically investigated. The two-photon absorption cross-section (sigma(2PA))values were measured by two-photon excited fluorescence which revealed that the four compounds possessed large sigma(2pA) values from 2011 to 4173 GM in the near infrared region. Theoretical calculations revealed that the compounds were all provided with interesting intramolecular charge transfer generated from one branch to the other which contributed to the large sigma(2PA) values. Cytotoxicity tests indicated that all these compounds had good biocompatibility for living cells, both one- and two-photon fluorescence microscopy studies showed the potential application of the four new compounds in cell imaging due to the large sigma(2pA) and appropriate biocompatibility. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.dyepig.2016.11.019
• 作为产物：
  描述：

  异佛尔酮 、 氰乙酸乙酯 在 sodium acetate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以52.72%的产率得到(Z)-ethyl 2-cyano-2-(3, 5, 5-trimethylcyclohex-2-en-1-ylidene)acetate
  参考文献：
  名称：

  Methoxy supported, deep red emitting mono, bis and tris triphenylamine-isophorone based styryl colorants: Synthesis, photophysical properties, ICT, TICT emission and viscosity sensitivity

  摘要：

  A novel strategy for the synthesis of triphenylamine based and methoxy supported deep red emitting push-pull chromophores is developed. The methoxy groups though not in conjugation with the acceptor exhibited a red shifted absorption and emissions (670 nm) as compared to the unsubstituted analogues due to the improved donating ability of triphenylamine. The dyes show high molar extinction coefficients (1, 65,800 M-1 cm(-1)) and as the number of withdrawing groups increases the molar extinction coefficient and emission intensity increase. Positive solvatochromism (96 nm) was observed which is well supported by linear and multi-linear regression. The mono styryl dyes showed enhancement of fluorescence while the di and tri-styryl dyes show quenching of fluorescence in polar solvents, which is correlated with the intramolecular charge transfer and twisted intramolecular charge transfer. Viscosity induced emission enhancement has also been observed. The experimental. findings were correlated theoretically by using Density Functional theory computations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.08.025

文献信息

• 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：——
• LE, BAUT, G.;SPARFEL, L.;CLAIRC, C.;FLOCH, R.;DUCREY, P.;BENAZET, F.;LACR+, EUR. J. MED. CHEM., 1983, 18, N 5, 447-455
  作者：LE, BAUT, G.、SPARFEL, L.、CLAIRC, C.、FLOCH, R.、DUCREY, P.、BENAZET, F.、LACR+

  DOI：——

  日期：——
• Four asymmetric bis-branched triphenylamine derivatives with charge transfer from one branch to the other: Two-photon emissions and bio-imaging applications
  作者：Xiaoping Gan、Xinping Ge、Chengkai Zhai、Jun Zheng、Xuguang Tang、Yanchao Yang、Yupeng Tian、Xuanjun Zhang、Hongping Zhou

  DOI：10.1016/j.dyepig.2016.11.019

  日期：2017.3

  Four asymmetric bis-branched triphenylamine-cored compounds with different electron-withdrawing groups have been synthesized and their optical properties have been systematically investigated. The two-photon absorption cross-section (sigma(2PA))values were measured by two-photon excited fluorescence which revealed that the four compounds possessed large sigma(2pA) values from 2011 to 4173 GM in the near infrared region. Theoretical calculations revealed that the compounds were all provided with interesting intramolecular charge transfer generated from one branch to the other which contributed to the large sigma(2PA) values. Cytotoxicity tests indicated that all these compounds had good biocompatibility for living cells, both one- and two-photon fluorescence microscopy studies showed the potential application of the four new compounds in cell imaging due to the large sigma(2pA) and appropriate biocompatibility. (C) 2016 Published by Elsevier Ltd.
• Methoxy supported, deep red emitting mono, bis and tris triphenylamine-isophorone based styryl colorants: Synthesis, photophysical properties, ICT, TICT emission and viscosity sensitivity
  作者：Shantaram Kothavale、Nagaiyan Sekar

  DOI：10.1016/j.dyepig.2016.08.025

  日期：2017.1

  A novel strategy for the synthesis of triphenylamine based and methoxy supported deep red emitting push-pull chromophores is developed. The methoxy groups though not in conjugation with the acceptor exhibited a red shifted absorption and emissions (670 nm) as compared to the unsubstituted analogues due to the improved donating ability of triphenylamine. The dyes show high molar extinction coefficients (1, 65,800 M-1 cm(-1)) and as the number of withdrawing groups increases the molar extinction coefficient and emission intensity increase. Positive solvatochromism (96 nm) was observed which is well supported by linear and multi-linear regression. The mono styryl dyes showed enhancement of fluorescence while the di and tri-styryl dyes show quenching of fluorescence in polar solvents, which is correlated with the intramolecular charge transfer and twisted intramolecular charge transfer. Viscosity induced emission enhancement has also been observed. The experimental. findings were correlated theoretically by using Density Functional theory computations. (C) 2016 Elsevier Ltd. All rights reserved.