4-butyl-2-thiophenecarboxaldehyde | 163461-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-butyl-2-thiophenecarboxaldehyde
• 英文别名: 4-butyl-2-formylthiophene；4-butyl-2-thiophenecarbaldehyde；4-butylthiophene-2-carbaldehyde
• CAS: 163461-01-6
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: KPBMSKNWTGNKPX-UHFFFAOYSA-N

物化性质

• 沸点：
  265.1±28.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (1R,2R,3R,5S)-(-)-Isopinocampheylamine 、 4-butyl-2-thiophenecarboxaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 (1R,2R,3R,5S)-N-((4-butylthiophen-2-yl)methyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride
  参考文献：
  名称：

  发现抗金刚烷胺和奥司他韦抗甲型流感病毒的高强力基于花青胺的抑制剂。

  摘要：

  流行性感冒是由甲型流感病毒（IAV）引起的对公共健康的持续重大威胁。IAVs按表面蛋白血凝素（HA）和神经氨酸酶（NA）进行分类，它们都是药物发现的基本靶标。尽管人们经常从人或禽流感病毒中鉴定出NA抑制剂奥司他韦耐药株，这一点引起了极大的关注，但流感HA的结构和功能表征却为新的抗病毒治疗带来了希望。在这项研究中，我们探索了基于频胺的抗病毒药物的构效关系（SAR），并发现了强效抑制剂M090对抗耐金刚烷胺的病毒（包括2009 H1N1大流行毒株）和耐奥司他韦的病毒。作用机理的研究，特别是溶血抑制作用，表明M090靶向HA流感，它占据了HA 2结构域的高度保守的口袋，并通过在构象重排过程中“锁定” HA 2的弯曲状态来抑制病毒介导的膜融合。这项工作在HA蛋白中提供了新的结合位点，表明该口袋可能是广谱抗A型流感药物设计和开发的有希望的目标。

  DOI：

  10.1021/acs.jmedchem.8b00042
• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 、 正丁基硼酸 在 palladium diacetate 、 potassium carbonate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 、 甲苯 为溶剂， 反应 6.0h， 以6.4 g的产率得到4-butyl-2-thiophenecarboxaldehyde
  参考文献：
  名称：

  [EN] FORMYLTHIOPHENES AND THEIR USE IN FLAVOR AND FRAGRANCE COMPOSITIONS
  [FR] FORMYLTHIOPHÈNES ET LEUR UTILISATION DANS DES COMPOSITIONS D'ARÔME ET DE PARFUM

  摘要：

  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。

  公开号：

  WO2017079368A1

文献信息

• A vinyl flanked difluorobenzothiadiazole–dithiophene conjugated polymer for high performance organic field-effect transistors
  作者：Xianfeng Liang、Wandong Sun、Yanlin Chen、Luxi Tan、Zhengxu Cai、Zitong Liu、Lin Wang、Jing Li、Wei Chen、Lichun Dong

  DOI：10.1039/c7tc05360f

  日期：——

  Fluorine containing conjugated polymers have been widely applied in high performance organic solar cells, but their use in field-effect transistors is still quite limited. In this work, a conjugated polymer PTFBTV based on difluorobenzothiadiazole (DFBT) and dithiophene was synthesized, utilizing multiple vinylene as linkers. The polymer exhibits a relatively high hole mobility up to 2.0 cm2 V−1 s−1

  含氟共轭聚合物已被广泛应用于高性能有机太阳能电池中，但其在场效应晶体管中的应用仍然非常有限。在这项工作中，利用多个亚乙烯基作为接头，合成了基于二氟苯并噻二唑（DFBT）和二噻吩的共轭聚合物PTFBTV。聚合物显示出较高的空穴迁移率，最高可达2.0 cm 2 V -1 s -1与报道的基于DFBT的低聚噻吩基聚合物相比，它的结构复杂性要简单得多。聚合物薄膜表现出典型的“面对”分子取向。其单体的单晶显示氟与相邻质子之间存在非共价分子内接触，从而增强了骨架的共面性。同时，还观察到分子间F⋯F接触，这可能导致固态PTFBTV产生相当分散的层状结晶。
• The Discovery of Citral-Like Thiophenes in Fried Chicken
  作者：Robert J. Cannon、Nicole L. Curto、Cynthia M. Esposito、Richard K. Payne、Adam J. Janczuk、David O. Agyemang、Tingwei Cai、Xiao-Qing Tang、Michael Z. Chen

  DOI：10.1021/acs.jafc.7b01371

  日期：2017.7.19

  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.
• Detty, Michael R.; Hays, David S., Heterocycles, 1995, vol. 40, # 2, p. 925 - 938
  作者：Detty, Michael R.、Hays, David S.

  DOI：——

  日期：——
• Synthesis of Trithienylenevinylenes Bearing Dithiocarbonate Groups and Their Dithiophene−Tetrathiafulvalene Derivatives
  作者：Xin Chen、Norma R. de Tacconi、Ronald L. Elsenbaumer

  DOI：10.1021/jo901574v

  日期：2009.12.4

  A series of conjugated trithienylenevinylene compounds bearing dithiocarbonate groups were prepared by Wittig reactions. Dithiophene-tetrithiafulvalene (DT-TTF) derivatives can be readily prepared through trialkylphosphite-mediated coupling reactions of these trithienylenevinylene materials. All compounds were characterized by NMR, FT-IR, UV-vis, and mass spectroscopy.
• 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