3-decyl-2-formylthiophene | 382602-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-decyl-2-formylthiophene
• 英文别名: 3-decyl-2-thiophenecarbaldehyde；3-decylthiophene-2-carboxaldehyde；3-Decylthiophene-2-carbaldehyde
• CAS: 382602-25-7
• 化学式: C₁₅H₂₄OS
• 分子量: 252.421
• InChiKey: FXQQUKHACQHIRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  357.2±22.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-decyl-2-formylthiophene 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,5-bis(5-bromo-3-decylthiophen-2-yl)thiazolo[5,4-d]thiazole
  参考文献：
  名称：

  具有萘[1,2- b：5,6 - b' ]二噻吩核的晶体D-π-A有机小分子，用于溶液处理的有机太阳能电池

  摘要：

  在这项工作中，我们设计并合成了一种新的含有萘并[1,2- b：5,6- b' ]二噻吩的扩大π共轭供体-受体（D-A）小分子NDT（TTz）2，用于溶液处理的有机光伏。通过顺序的Suzuki和Stille合成了NDT（TTz）2，其中NDT（TTz）2包含噻吩桥接的萘并[1,2- b：5,6 - b' ]二噻吩作为中心稠合核心，三苯胺侧翼噻吩噻唑并噻唑作为间隔基偶联反应。NDT（TTz）2的热，物理化学和电化学性质已通过差示扫描量热法，热重分析法，紫外可见光谱，光致发光光谱，X射线衍射和循环伏安法进行了评估。如光伏应用所希望的那样，NDT（TTz）2具有良好的溶解性，热稳定性和井井有条的π-π堆叠结晶性。NDT（TTz）2的光学带隙和HOMO能级分别确定为2.0 eV和-5.23 eV。除了研究有机薄膜晶体管外，还通过与PC 71一起制造溶液处理的体异质结太阳能电池，研究了NDT（TTz）

  DOI：

  10.1016/j.orgel.2012.09.019
• 作为产物：
  描述：

  Decylmagnesium bromide 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-decyl-2-formylthiophene
  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

• [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。
• Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells
  作者：Pranabesh Dutta、Wooseung Yang、Seung Hun Eom、Soo-Hyoung Lee

  DOI：10.1016/j.orgel.2011.11.016

  日期：2012.2

  Two new small molecules, 5,5-bis(2-triphenylamino-3-decylthiophen-2-yl)-2,2-bithiazole (M1) and 2,5-bis(2-triphenylamino-3-decylthiophen-2-yl) thiazolo[5,4-d]thiazole (M2) based on an electron-donor triphenylamine unit and electron-acceptor thiophene-thiazolothiazole or thiophene-bithiazole units were synthesized by a palladium(0)-catalyzed Suzuki coupling reaction and examined as donor materials for application in organic solar cells. The small molecules had an absorption band in the range of 300-560 nm, with an optical band gap of 2.22 and 2.25 for M1 and M2, respectively. As determined by cyclic voltammetry, the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of M1 were -5.27 eV and -3.05 eV, respectively, which were 0.05 eV and 0.02 eV greater than that of M2. Photovoltaic properties of the small molecules were investigated by constructing bulk-heterojunction organic solar cell (OSC) devices using M1 and M2 as donors and fullerene derivatives, 6,6-phenyl-C61-butyric acid methyl ester (PC61BM) and 6,6-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptors with the device architecture ITO/PEDOT:PSS/M1 or M2:PCBM/LiF/Al. The effect of the small molecule/fullerene weight ratio, active layer thickness, and processing solvent were carefully investigated to improve the performance of the OSCs. Under AM 1.5 G 100 mW/cm(2) illumination, the optimized OSC device with M1 and PC71BM at a weight ratio of 1: 3 delivered a power conversion efficiency (PCE) of 1.30%, with a short circuit current of 4.63 mA/cm(2), an open circuit voltage of 0.97 V, and a fill factor of 0.29. In contrast, M2 produced a better performance under identical device conditions. A PCE as high as 2.39% was recorded, with a short circuit current of 6.49 mA/cm(2), an open circuit voltage of 0.94 V, and a fill factor of 0.39. (C) 2011 Elsevier B. V. All rights reserved.
• FORMYLTHIOPHENES AND THEIR USE IN FLAVOR AND FRAGRANCE COMPOSITIONS
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3371291A1

  公开（公告）日：2018-09-12