3-辛基-2-噻吩甲醛 | 924728-11-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-辛基-2-噻吩甲醛
• 英文名称: 3-octylthiophene-2-carbaldehyde
• 英文别名: 3-Octyl-2-thiophenecarboxaldehyde
• CAS: 924728-11-0
• 化学式: C₁₃H₂₀OS
• 分子量: 224.367
• InChiKey: UHQKPLUDRGQDBW-UHFFFAOYSA-N

物化性质

• 沸点：
  326.4±22.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-辛基-2-噻吩甲醛 在 四氯化钛 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 4-Octyl-5-[(E)-2-(3-octyl-thiophen-2-yl)-vinyl]-thiophene-2-carbaldehyde
  参考文献：
  名称：

  封端有1,3-二硫代-2-亚烷基的可溶性亚噻吩乙烯低聚物

  摘要：

  描述了用1，3-二硫代-2-亚烷基封端的噻吩亚乙烯基低聚物的合成。CV分析表明，这些化合物可以在狭窄的电势窗口内被氧化成四阳离子状态

  DOI：

  10.1016/0040-4039(96)01343-3
• 作为产物：
  描述：

  正辛基镁溴盐 在 1,2-双(二苯基膦)乙烷氯化镍 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 9.0h， 生成 3-辛基-2-噻吩甲醛
  参考文献：
  名称：

  The Discovery of Citral-Like Thiophenes in Fried Chicken

  摘要：

  The isomers of 3,7-dimethyl-2,6-octadienal, more commonly known together as citral, are two of the most notable natural compounds in the flavor and fragrance industry. However, both isomers are inherently unstable, limiting their potential use in various applications. To identify molecules in nature that can impart the fresh lemon character of citral while demonstrating stability under acidic and thermal conditions has been a major challenge and goal for the flavor and fragrance industry. In the study of fried chicken, several alkyl thiophenecarbaldehydes were identified by gas chromatography-mass spectrometry and gas chromatography-olfactometry that provided a similar citral-like aroma. The potential mechanism of formation in fried chicken is discussed. Furthermore, in order to explore the organoleptic properties of this structural backbone, a total of 35 thiophenecarbaldehyde derivatives were synthesized or purchased for evaluation by odor and taste. Certain organoleptic trends were observed as the length of the alkyl or alkenyl chain increased or when the chain was moved to different positions on the thiophene backbone. The 3-substituted alkyl thiophenecarbaldehydes, specifically 3-butyl-2-thiophenecarbaldehyde and 3-(3-methylbut-2-en-1-yl)-2-thiophenecarbaldehyde, exhibited strong citrus and citral-like notes. Several alkyl thiophenecarbaldehydes were tested in high acid stability trials (4 degrees C vs 38 degrees C) and outperformed citral both in terms of maintaining freshness over time and minimizing off-notes. Additional measurements were completed to calculate the odor thresholds for a select group of thiophenecarbaldehydes, which were found to be between 4.7-215.0 ng/L in air.

  DOI：

  10.1021/acs.jafc.7b01371

文献信息

• Phenacyl-Thiophene and Quinone Semiconductors Designed for Solution Processability and Air-Stability in High Mobility n-Channel Field-Effect Transistors
  作者：Joseph A. Letizia、Scott Cronin、Rocio Ponce Ortiz、Antonio Facchetti、Mark A. Ratner、Tobin J. Marks

  DOI：10.1002/chem.200901513

  日期：2010.2.8

  2′′′‐quaterthiophene (2), poly[5,5′′′‐(perfluorophenac‐2‐yl)‐4′,4′′‐dioctyl‐2,2′:5′,2′′:5′′,2′′′‐quaterthiophene) (3), 5,5′′′‐bis(perfluorophenacyl)‐4,4′′′‐dioctyl‐2,2′:5′,2′′:5′′,2′′′‐quaterthiophene (4), 2,7‐bis((5‐perfluorophenacyl)thiophen‐2‐yl)‐9,10‐phenanthrenequinone (5), 2,7‐bis[(5‐phenacyl)thiophen‐2‐yl]‐9,10‐phenanthrenequinone (6), and 2,7‐bis(thiophen‐2‐yl)‐9,10‐phenanthrenequinone, (7). Optical and

  可在普通有机溶剂中加工或表现出空气稳定运行的场效应晶体管（FET）的电子传输有机半导体（n沟道）很少。这项研究通过合理的分子设计和n沟道FET空气稳定性的计算预测来应对这些挑战。据报道，一系列七种基于苯甲酰噻吩的材料在分子结构和还原潜能方面均具有系统性变化。这些化合物如下：5,5''-双（全氟苯基羰基）-2,2'：5'，-2':: 5''，2'''-四噻吩（1），5,5'' '-双（苯甲酰基）-2,2'：5'，2''：5''，2'''-四噻吩（2），聚[5,5'''-（全氟苯-2-基）- 4′，4′′-二辛基-2,2′：5′，2′′：5′′，2′′′-四噻吩）（3），5,5'''-双（全氟苯甲酰基）-4,4'''-二辛基-2,2'：5'，2''：5''，2'''-四噻吩（4），2 ，7-双（（5-全氟苯甲酰基）噻吩-2-基）-9,10-菲醌（5），2,7-双[（5-苯甲酰基）噻吩-2-基]
• THIAZOLOTHIAZOLE DERIVATIVE
  申请人：HORIBA Koji

  公开号：US20100137611A1

  公开（公告）日：2010-06-03

  A thiazolothiazole derivative is represented by the following Formula (I). In Formula (I), each R 1 independently represents a straight chain alkyl group having 3 to 20 carbon atoms, a straight chain alkoxy group having 3 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms; and each R 2 independently represents a hydrogen atom, a straight chain alkyl group having 1 to 20 carbon atoms, a straight chain alkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms.

  一种噻唑噻唑衍生物由以下化学式（I）表示。在化学式（I）中，每个R1独立地代表具有3到20个碳原子的直链烷基基团，具有3到20个碳原子的直链烷氧基团，具有3到20个碳原子的支链烷基基团，或具有3到20个碳原子的支链烷氧基团；每个R2独立地代表氢原子，具有1到20个碳原子的直链烷基基团，具有1到20个碳原子的直链烷氧基团，具有3到20个碳原子的支链烷基基团，或具有3到20个碳原子的支链烷氧基团。
• ORGANIC ELECTROLUMINESCENT DEVICE AND DISPLAY MEDIUM
  申请人：IMAI Akira

  公开号：US20100276672A1

  公开（公告）日：2010-11-04

  An organic electroluminescent device includes: a pair of electrodes including a positive electrode and a negative electrode, at least one of the electrodes being transparent or semi-transparent; and an organic compound layer including one or more layers interposed between the pair of electrodes, at least one layer included in the organic compound layer containing one or more compounds represented by the following formula (I): in formula (I), R 1 s each independently representing a linear alkyl, linear alkoxy, branched alkyl, or branched alkoxy group having from 3 to 20 carbon atoms; and R 2 s each independently representing a hydrogen atom, a linear alkyl group having from 1 to 20 carbon atoms, a linear alkoxy group having from 1 to 20 carbon atoms, a branched alkyl group having from 3 to 20 carbon atoms, or a branched alkoxy group having from 3 to 20 carbon atoms.

  一种有机电致发光器件包括：一对电极，包括一个正电极和一个负电极，其中至少一个电极是透明或半透明的；以及一个有机化合物层，包括夹在一对电极之间的一个或多个层，有机化合物层中至少包含一个含有一个或多个以下式(I)所代表的化合物的层：在式(I)中，R1分别独立地表示具有3至20个碳原子的直链烷基，直链烷氧基，支链烷基或支链烷氧基；R2分别独立地表示氢原子，具有1至20个碳原子的直链烷基，具有1至20个碳原子的直链烷氧基，具有3至20个碳原子的支链烷基，或具有3至20个碳原子的支链烷氧基。
• [EN] FORMYLTHIOPHENES AND THEIR USE IN FLAVOR AND FRAGRANCE COMPOSITIONS<br/>[FR] FORMYLTHIOPHÈNES ET LEUR UTILISATION DANS DES COMPOSITIONS D'ARÔME ET DE PARFUM
  申请人：INT FLAVORS & FRAGRANCES INC

  公开号：WO2017079368A1

  公开（公告）日：2017-05-11

  The present invention is directed to novel organoleptic compounds, a process of augmenting, enhancing or imparting taste to a material selected from the group consisting of a foodstuff, a chewing gum, a dental product, an oral hygiene product and a medicinal product comprising the step of incorporating an olfactory acceptable amount of such novel organoleptic compounds, and a process of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of such novel organoleptic compounds.

  本发明涉及新型感官化合物，一种增强、提升或赋予食品、口香糖、牙科产品、口腔卫生产品和药品中所选材料的味道的方法，包括将这种新型感官化合物的嗅觉可接受量合并到其中的步骤，以及通过添加这种新型感官化合物的嗅觉可接受量来改进、增强或修改香精配方的方法。
• Electronic properties of thienylene vinylene oligomers: synthesis and theoretical study
  作者：G. Neculqueo、V. Rojas Fuentes、A. López、R. Matute、S. O. Vásquez、F. Martínez

  DOI：10.1007/s11224-012-9979-0

  日期：2012.12

  (E)-1,2-bis(2-thienyl)vinylene (TV), (E)-1,2-bis(3-octyl-2-thienyl)vinylene (TOV), (E)-1,2-bis(3-(2-ethylhexyl)-2-thienyl)vinylene (T2EHV), and (E)-1,2-bis-[2,2’-bithienyl] vinylene (BTV) have been synthesized by a combination of formylation reaction and Mc Murry dimerization. UV–Vis spectra of BTV showed the longest wavelength absorption, TOV and T2EHV showed a bathochromic shift to the red compared with TV, due to an increment of delocalization of the conjugated π-system as the result of the weakening of the carbon–carbon double bonds of the thienyl rings due to the substitution of one hydrogen by the alkyl group. Based on optical data, the effect of linear and branched alkyl chain and extension of conjugation length on the electronic properties is discussed. 1H, 13C-NMR, UV–Visible, Fluorescence data are discussed and theoretical DFT and TD-DFT calculations of ground state and excited states have been also considered in the analysis and explanation of results.

  (E)-1,2-双(2-噻吩基)亚乙烯基 (TV)、(E)-1,2-双(3-辛基-2-噻吩基)亚乙烯基 (TOV)、(E)-1,2-通过甲酰化组合合成了双(3-(2-乙基己基)-2-噻吩基)亚乙烯基(T2EHV)和(E)-1,2-双-[2,2'-联噻吩基]亚乙烯基(BTV)反应和 Mc Murry 二聚化。 BTV 的紫外-可见光谱显示出最长的波长吸收，TOV 和 T2EHV 与 TV 相比显示出红移，这是由于碳-碳双键减弱导致共轭 π 系统的离域增加。由于一个氢被烷基取代而形成的噻吩环键。基于光学数据，讨论了直链和支链烷基链以及共轭长度的延长对电子性能的影响。讨论了 1H、13C-NMR、紫外可见光、荧光数据，并在结果分析和解释中考虑了基态和激发态的理论 DFT 和 TD-DFT 计算。