ethyl 2-cyano-3-(5-formyl-1H-pyrrol-2-yl)acrylate | 70582-64-8

• 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 2-cyano-3-(5-formyl-1H-pyrrol-2-yl)acrylate
• 英文别名: ethyl α-cyano-5-formyl-2-pyrroleacrylate；ethyl 2-cyano-3-(5-formyl-1H-pyrrol-2-yl)prop-2-enoate
• CAS: 70582-64-8
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: RNGNFMMGVFLSPX-UHFFFAOYSA-N

物化性质

• 沸点：
  434.1±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-3-(5-formyl-1H-pyrrol-2-yl)acrylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以40%的产率得到1H-吡咯-2,5-二甲醛
  参考文献：
  名称：

  Double intramolecular hydrogen transfer assisted dual emission in a carbazole-embedded porphyrin-like macrocycle

  摘要：

  嵌入咔唑基囊状卟啉类大环3，带有一个meso-吡咯基取代基，表现出双重荧光性。光物理研究揭示了通过双分子内氢转移产生的两种可区分的NH-互变异构体。

  DOI：

  10.1039/d1cc00868d
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 ethyl 2-cyano-3-(1H-pyrrol-2-yl)acrylate 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以76%的产率得到ethyl 2-cyano-3-(5-formyl-1H-pyrrol-2-yl)acrylate
  参考文献：
  名称：

  2,5-双[ N-（2,6-间苯二甲撑亚氨基甲基]吡咯基钴（II）的合成和结构：一电子氧化的氧化还原非纯配体行为的证据

  摘要：

  由CoCl 2和（Mes 2 pyr）H制备标题配合物Co（Mes 2 pyr）Cl 2。代替预期的（Mes 2 pyr）CoCl配合物，分离具有式（Mes 2 pyr）CoCl 2的配合物，其中Mes 2 pyr配体的角应变导致三个配体供体原子中只有两个与金属连接。仔细检查结构，光谱和磁性特征表明，该化合物最能描述为高旋转Co（II）与中性自由基配体的复合物。

  DOI：

  10.1021/acs.inorgchem.6b02898

文献信息

• Synthesis, molecular structure, multiple interactions and chemical reactivity analysis of a novel ethyl 2-cyano-3-[5-(hydrazinooxalyl–hydrazonomethyl)-1H-pyrrol-2-yl]-acrylate and its dimer: A combined experimental and theoretical (DFT and QTAIM) approach
  作者：R.N. Singh、Amit Kumar、R.K. Tiwari、Poonam Rawat

  DOI：10.1016/j.molstruc.2013.01.011

  日期：2013.4

  the various intra and intermolecular interactions in dimer and their corresponding second order stabilization energy (E(2)). A combined theoretical and experimental vibrational analysis confirms the existence of dimer and the binding energy of dimer is calculated as 9.21 kcal/mol using DFT calculations. To determine the energy and nature of different interactions topological parameters at bond critical

  摘要 新合成的乙基 2-氰基-3-[5-(hydrazinooxalyl-hydrazonomethyl)-1H-pyrrol-2-yl]-丙烯酸酯 (3) 的详细光谱分析已使用 1H 和 13C NMR、UV-可见光、FT-IR 和质谱技术。所有的量子化学计算都是使用 DFT 理论水平、B3LYP 泛函和 6-31G(d,p) 作为基组进行的。1H 和 13C NMR 化学位移是在 DMSO-d6 中使用包括原子轨道 (GIAO) 方法的规范计算的。TD-DFT 用于计算各种电子跃迁的能量 (E)、振荡强度 (f) 和波长吸收最大值 (λmax) 及其在分子内的性质。进行自然键轨道 (NBO) 分析以研究二聚体中的各种内部和分子间相互作用及其相应的二阶稳定能 (E(2))。组合的理论和实验振动分析证实了二聚体的存在，并且使用 DFT 计算计算出二聚体的结合能为 9.21 kcal/mol。为了确定键临界点
• Synthesis, spectroscopic and structural evaluation of ethyl 2-cyano-3-{5-[(4-nitro-benzoyl)-hydrazonomethyl]-1H-pyrrol-2-yl}-acrylate using experimental and theoretical approaches
  作者：R.N. Singh、Amit Kumar、Poonam Rawat、Anchal Srivastsva

  DOI：10.1016/j.molstruc.2013.07.001

  日期：2013.10

  acceptor. To determine the strength and nature of hydrogen bonding, topological parameters at bond critical points (BCP) have been analyzed by ‘Quantum theory of atoms in molecules’ (QTAIM) in detail. The result of hydrogen bonding is obvious in 1H NMR, FT-IR and ESP map as down field chemical shift, vibrational red shift and absence of blue colur relative to pyrrole N H proton, respectively. Global electrophilicity

  摘要 一种新的含芳酰腙、乙基 2-氰基-3-5-[(4-硝基-苯甲酰基)-腙甲基]-1H-吡咯-2-基}-丙烯酸酯 (ECNBHPA) 的 C-乙烯基吡咯，衍生自 2-氰基乙基-3-(5-formyl-1H-pyrrol-2-yl)-丙烯酸酯和 4-硝基苯甲酰肼已通过各种光谱技术（1H NMR、13C NMR、质谱、紫外-可见光、发射、FT-IR）表征. TD-DFT 已被用于计算分子内的各种电子激发及其性质。ECNBHPA 的发射光谱显示了标题分子的光致发光行为。已进行自然键轨道 (NBO) 分析以探索分子内的各种共轭/超共轭相互作用及其二阶稳定能 (E(2))。结合实验和理论振动分析表明，作为质子供体的吡咯 NH 和作为质子受体的氰化物 N 原子之间存在经典的氢键 N1 H29⋯N9。为了确定氢键的强度和性质，已通过“分子中原子的量子理论”（QTAIM）详细分析了键临界点（BCP）处的拓扑参数。氢键的结果在
• Visualization of latent fingerprints using an AIE-active unsymmetrical azine: 2-Naphthol-pyrrole acrylate conjugate and its fluorescent sensing of Cu2+ and S2− ions, smartphone and logic gate applications
  作者：Balamurugan Tharmalingam、Ottoor Anitha、Janardhanan Aiswarya、Thangaraj Thiruppathiraja、Senthilkumar Lakshmipathi、Balasubramanian Murugesapandian

  DOI：10.1016/j.jphotochem.2023.114757

  日期：2023.8

  restriction of intramolecular rotation (RIR). The aggregation feature of LH2 was supported by DLS and FE-SEM studies. Further, the practical application of aggregates was established by imaging latent fingerprints (LFPs) over a TLC glass slide and other platofrms. In addition, the probe LH2 could selectively detect Cu2+ ions colorimetrically and fluorometrically in DMSO: H2O mixture over the other metal

  通过简单缩合乙基-α-氰基-5-甲酰基-2-吡咯丙烯酸酯和1- (亚肼基甲基)萘-2-醇，设计并开发了一种新型的 AIE 活性不对称吖嗪基探针LH 2。合成的探针LH 2通过核磁共振和质谱方法进行了表征。在 DMSO-H 2中检测了吖嗪衍生物LH 2的聚集诱导发光 (AIE) 行为O 混合物，其中该化合物在纯有机溶剂 DMSO 中显示出微弱的发射，并且发现由于分子内旋转 (RIR) 的限制，随着水分数的增加，发射在 608 nm 处增强。DLS 和 FE-SEM 研究支持LH 2的聚集特征。此外，通过在薄层色谱载玻片和其他平台上对潜在指纹 (LFP) 进行成像，确定了聚集体的实际应用。此外，探针LH 2可以选择性地通过比色法和荧光法检测DMSO：H 2 O混合物中的Cu 2+离子，而不是其他金属离子。更重要的是，LH 2肉眼可察觉的颜色变化已与 RGB 颜色值应用程序完美集成，使其适用于现场轻松实时检测
• Experimental and DFT study on a newly synthesized ethyl 2-cyano-3-[5-(phenyl-hydrazonomethyl)-1H-pyrrol-2-yl]-acrylate
  作者：Poonam Rawat、R.N. Singh

  DOI：10.1016/j.molstruc.2014.10.047

  日期：2015.2

  A newly synthesized ethyl 2-cyano-3-[5-(phenyl-hydrazonomethyl)-1H-pyrrol-2-yl]-acrylate (ECPHPA) has been characterized by experimental measurements. The theoretically calculated results are in accordance with the experimental studies. All calculations have been performed using B3LY/6-31G(d,p) basis set. The oscillatory strength (f) and wavelength of various electronic excitations show pi -> pi* nature of transitions. Natural bond orbital (NBO) analysis shows intramolecular conjugative/hyperconjugative interactions within the studied molecule. The result of hydrogen bonding is obvious in H-1 NMR, FT-IR and NBO analyses as down field chemical shift, vibrational red shift and pi(1)(C8-N9) -> sigma*(N1-H24) interaction, respectively. Global electrophilicity index (omega = 4.80 eV) shows that ECPHPA is a strong electrophile and local reactivity descriptors indicate have reactive sites within molecule and undergo for the formation of various heterocyclic compounds. The first hyperpolarizability (beta(o)) computed found to be 35.76 x 10(-30) esu, evaluate the suitability of compound for non-linear optical (NLO) response. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis, molecular structure, photoluminescence, multiple interaction, chemical reactivity and first hyperpolarizability analysis of ethyl 2-cyano-3-{5-(4-methylbenzenesulfonyl)-hydrazonomethyl]-1H-pyrrol-2-yl}-acrylate: Experimental and quantum chemical approaches
  作者：R.N. Singh、Poonam Rawat、Amit Kumar

  DOI：10.1016/j.molstruc.2013.12.080

  日期：2014.3

  A detailed spectroscopic, molecular structure, photoluminescence, multiple interaction, chemical reactivity and first hyperpolarizability analysis of a newly synthesized ethyl 2-cyano-3-5-[(4-methylbenzenesulfonyl}-hydrazonomethyl]-1H-pyrrol-2-yl)-acrylate (ECMHPA) has been carried out. TD-DFT is used to find various electronic excitations and their nature within molecule. The emission spectra show photoluminescence behavior of title molecule in yellow region. The red shift in both the proton donor (pyrrole N-H) and proton acceptor (S=O) group designates the presence of intermolecular hydrogen bonding N1-H2...O49 and N46-H47...O4. The binding energy of dimer formation has been calculated to be 12.12 kcal/mol after basis set superposition error (BSSE) correction. The global electrophilicity index (omega = 5.44 eV) shows that ECMHPA is a strong electrophile. First hyperpolarizability (beta(0)) of ECMHPA has been computed to evaluate non-linear optical (NLO) response of the investigated molecule. (C) 2014 Elsevier B.V. All rights reserved.