3-[5-(piperidin-1-yl)thiophen-2-yl]prop-2-enal | 195823-60-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[5-(piperidin-1-yl)thiophen-2-yl]prop-2-enal
• 英文别名: (2E)-3-[5-(N-piperidinyl)thiophene-2yl]acrylaldehyde；(E)-3-(5-piperidin-1-ylthiophen-2-yl)prop-2-enal
• CAS: 195823-60-0
• 化学式: C₁₂H₁₅NOS
• 分子量: 221.323
• InChiKey: WUIFXQCGGITCJL-SNAWJCMRSA-N

物化性质

• 熔点：
  91.0-93.5 °C(Solv: hexane (110-54-3))
• 沸点：
  409.6±35.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[5-(piperidin-1-yl)thiophen-2-yl]prop-2-enal 在 盐酸 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Large Quadratic Hyperpolarizabilities with Donor–Acceptor Polyenes Exhibiting Optimum Bond Length Alternation: Correlation Between Structure and Hyperpolarizability

  摘要：

  AbstractDonor–acceptor polyenes of various lengths, and that combine aromatic electron‐donating moieties with powerful heterocyclic electron‐withdrawing terminal groups, have been synthesized and characterized as efficient nonlinear optical (NLO) chromophores. Their linear and nonlinear optical properties have been investigated, and variations in these properties have been related to ground‐state polarization (dipole μ) and structure. In particular, unprecedented quadratic hyperpolarizabilities (β) have been achieved (up to β(0) = 1500 × 10−30 esu) by reduction of the bond‐length alternation (BLA) in the polyenic chain. In each series of homologous compounds, increasing the number n of conjugated double bonds in the polyenic chain results in a marked bathochromic shift, more pronounced BLA, and exponential increases in μβ(0) values. As a result, polyenic chromophores displaying excellent optical quadratic nonlinearities (μβ values as large as 100 times that of the quadratic NLO benchmark 4‐dimethyl‐amino‐4′‐nitrostilbene (DANS)), as well as satisfactory solubility, have been obtained.

  DOI：

  10.1002/chem.19970030717
• 作为产物：
  描述：

  哌啶 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.5h， 生成 3-[5-(piperidin-1-yl)thiophen-2-yl]prop-2-enal
  参考文献：
  名称：

  丙二酸衍生物作为推挽分子中的电子吸收单元的职责

  摘要：

  以2-（N-哌啶基）噻吩中心供体为基础，制备了32种具有系统变化的丙二酸衍生的外周受体的模型推挽分子。通过修改π接头和结构排列（线性与四极D–π–A系统），可以实现进一步的性能调节。丙二酸衍生物，例如氰基乙酸，丙二酸，丙二酸二乙酯，Meldrum酸和N，N'-二丁基（硫代）巴比妥酸以及1，3-二酮类似物二甲酮和茚满-1，3-二酮被用作受体部分。Knoevenagel与四种噻吩醛的缩合反应以令人满意的产率提供了目标发色团。通过包括X射线分析，差示扫描量热法，电化学和UV / Vis吸收光谱的实验以及通过DFT计算来检查丙二酸受体的吸电子能力。结构-财产关系的细节已经阐明。根据增加的吸电子能力，广泛使用的丙二酸受体单元可以订购：丙二酸二乙酯≤氰基乙酸

  DOI：

  10.1002/ejoc.201700070

文献信息

• T-Shaped (Donor-π-)₂Acceptor-π-Donor Push-Pull Systems Based on Indan-1,3-dione
  作者：Parmeshwar Solanke、Filip Bureš、Oldřich Pytela、Milan Klikar、Tomáš Mikysek、Loic Mager、Alberto Barsella、Zdeňka Růžičková

  DOI：10.1002/ejoc.201500525

  日期：2015.8

  Sixteen model (donor–π–)2acceptor–π–donor [(D–π–)2A–π–D] molecules with an extraordinary T-shaped arrangement were designed and synthesized. Indan-1,3-dione was employed as a central acceptor with electron donors linked at the C-2, C-4, and C-7 positions. These push–pull molecules represent a first systematic modification of an indan-1,3-dione-fused benzene ring. The structures and properties of all

  设计并合成了 16 种具有非凡 T 形排列的模型 (donor–π–)2acceptor–π–donor [(D–π–)2A–π–D] 分子。Indan-1,3-dione 用作中央受体，电子供体连接在 C-2、C-4 和 C-7 位置。这些推拉分子代表了对茚满-1,3-二酮稠合苯环的首次系统修饰。通过 X 射线分析、电化学、紫外/可见吸收光谱、差示扫描量热法、电场诱导二次谐波产生 (EFISHG) 研究和 DFT 计算研究了所有目标分子的结构和性质。对所有收集的数据进行了全面评估，并评估了结构-性能关系。通过各种长度的 π 系统连接在 C-2 位置的电子供体对研究的性质影响最显着。C-4 和 C-7 处的侧供体可被描述为辅助性的，并不支配观察到的性质。然而，在这方面，噻吩是比 N,N-二甲基苯胺更有效的供体。因此，带有哌啶基噻吩供体的茚满-1,3-二酮在 C-2 处通过亚丙烯间隔基连接，在
• Large Quadratic Hyperpolarizabilities with Donor–Acceptor Polyenes Exhibiting Optimum Bond Length Alternation: Correlation Between Structure and Hyperpolarizability
  作者：M. Blanchard-Desce、V. Alain、P. V. Bedworth、S. R. Marder、A. Fort、C. Runser、M. Barzoukas、S. Lebus、R. Wortmann

  DOI：10.1002/chem.19970030717

  日期：1997.7

  AbstractDonor–acceptor polyenes of various lengths, and that combine aromatic electron‐donating moieties with powerful heterocyclic electron‐withdrawing terminal groups, have been synthesized and characterized as efficient nonlinear optical (NLO) chromophores. Their linear and nonlinear optical properties have been investigated, and variations in these properties have been related to ground‐state polarization (dipole μ) and structure. In particular, unprecedented quadratic hyperpolarizabilities (β) have been achieved (up to β(0) = 1500 × 10−30 esu) by reduction of the bond‐length alternation (BLA) in the polyenic chain. In each series of homologous compounds, increasing the number n of conjugated double bonds in the polyenic chain results in a marked bathochromic shift, more pronounced BLA, and exponential increases in μβ(0) values. As a result, polyenic chromophores displaying excellent optical quadratic nonlinearities (μβ values as large as 100 times that of the quadratic NLO benchmark 4‐dimethyl‐amino‐4′‐nitrostilbene (DANS)), as well as satisfactory solubility, have been obtained.
• Malonic Acid Derivatives on Duty as Electron-Withdrawing Units in Push-Pull Molecules
  作者：Milan Klikar、Veronika Jelínková、Zdeňka Růžičková、Tomáš Mikysek、Oldřich Pytela、Miroslav Ludwig、Filip Bureš

  DOI：10.1002/ejoc.201700070

  日期：2017.5.18

  molecules with systematically varied malonic acid-derived peripheral acceptors have been prepared. Further property tuning has been achieved by modifying the π-linker and the structural arrangement (linear vs. quadrupolar D–π–A systems). Malonic acid derivatives such as cyanoacetic acid, malondinitrile, diethyl malonate, Meldrum′s acid, and N,N′-dibutyl(thio)barbituric acid as well as 1,3-diketo analogues

  以2-（N-哌啶基）噻吩中心供体为基础，制备了32种具有系统变化的丙二酸衍生的外周受体的模型推挽分子。通过修改π接头和结构排列（线性与四极D–π–A系统），可以实现进一步的性能调节。丙二酸衍生物，例如氰基乙酸，丙二酸，丙二酸二乙酯，Meldrum酸和N，N'-二丁基（硫代）巴比妥酸以及1，3-二酮类似物二甲酮和茚满-1，3-二酮被用作受体部分。Knoevenagel与四种噻吩醛的缩合反应以令人满意的产率提供了目标发色团。通过包括X射线分析，差示扫描量热法，电化学和UV / Vis吸收光谱的实验以及通过DFT计算来检查丙二酸受体的吸电子能力。结构-财产关系的细节已经阐明。根据增加的吸电子能力，广泛使用的丙二酸受体单元可以订购：丙二酸二乙酯≤氰基乙酸