3-butyl-2-thiophenecarboxaldehyde | 163460-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-butyl-2-thiophenecarboxaldehyde
• 英文别名: 3-butyl-2-formylthiophene；3-butyl-2-thiophenecarbaldehyde；3-Butylthiophene-2-carbaldehyde
• CAS: 163460-99-9
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: NQJJSJLPJFVZHC-UHFFFAOYSA-N

物化性质

• 沸点：
  260.7±20.0 °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 、 3-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-((3-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：

  3-丁基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 3.5h， 生成 3-butyl-2-thiophenecarboxaldehyde
  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。
• [EN] PERIPHERAL VASODILATING AGENT CONTAINING N-ACYLATED 4-AMINO PIPERIDINE DERIVATIVES AS ACTIVE INGREDIENTS<br/>[FR] AGENTS VASODILATATEURS PERIPHERIQUES COMPORTANT COMME PRINCIPE ACTIF DES DERIVES DE LA PIPERIDINE 4-AMINO N-ACYLEE
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：WO1994022826A1

  公开（公告）日：1994-10-13

  (EN) The present invention relates to novel peripheral vasodilating agents characterized by each containing as an active ingredient, a piperidine derivative or pharmaceutically acceptable salt thereof having excellent peripheral vasodilating activity. Said piperidine derivative or pharmaceutically acceptable salt thereof is represented by general formula (1), wherein R, R1 and R2 are the same as defined above.(FR) Nouveaux agents dilatateurs périphériques contenant individuellement comme principe actif un dérivé de la pipéridine ou l'un de ses sels pharmaco-compatibles et présentant une excellente activité vasodilatatrice périphérique. Lesdits dérivés de la pipéridine ou leurs sels pharmaco-compatibles sont représentés par la formule générale (1) où R, R1 et R2 sont conformes à la définition ci-dessus.

  (EN) 本发明涉及一种新型周围血管扩张剂，其特征在于每种扩张剂均包含作为活性成分的哌啶衍生物或其药学上可接受的盐，具有出色的周围血管扩张活性。所述哌啶衍生物或其药学上可接受的盐由通式（1）表示，其中R，R1和R2与上述定义相同。 (FR) La présente invention concerne de nouveaux agents vasodilatateurs périphériques caractérisés chacun par la présence, en tant que principe actif, d'un dérivé de pipéridine ou de l'un de ses sels pharmaceutiquement acceptables présentant une excellente activité vasodilatatrice périphérique. Lesdits dérivés de pipéridine ou leurs sels pharmaceutiquement acceptables sont représentés par la formule générale (1), dans laquelle R, R1 et R2 sont tels que définis ci-dessus.
• Tertiary amine compounds
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0253502A2

  公开（公告）日：1988-01-20

  According to the invention there are provided compounds having the general formula (I): and stereoisomers thereof, wherein one of X and Y, but not both, is a group of the formula (II): and the other of X and Y is a hydrogen atom, a halogen atom, or an alkyl, cycloalkyl, cycloalkylalkyl. alkenyl, alkynyl, aryl, aralkyl, alkoxy, aryloxy or haloalkyl group or a group wherein R9, R10 and R11 can be alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or aryl, Z is an oxygen atom, a sulphur atom or an -NH-group, A and B have the same significance as X or Y excluding a group of formula (II), R'. R2, R3 and R4 each represent a hydrogen atom, a halogen atom or an alkyl group containing from I to 4 carbon atoms, R5 and R6 each represent a hydrogen atom or an alkyl group containing from I to 4 carbon atoms, and R7 and R8 each represent an alkyl group containing from I to 4 carbon atoms or R7 and R8 together with the adjacent nitrogen atom form a heterocyclic ring which may optionally contain an additional hetero atom; and acid addition salts thereof.

  根据本发明，提供了具有通式（I）的化合物及其立体异构体： 及其立体异构体，其中 X 和 Y 中的一个（但不是两个）是式（II）的基团： X和Y中的另一个是氢原子、卤素原子或烷基、环烷基、环烷基烷基、烯基、炔基、芳基、芳烷基、烷氧基、芳氧基或卤代烷基或 其中 R9、R10 和 R11 可以是烷基、烯基、炔基、环烷基、环烷烃基或芳基，Z 是氧原子、硫原子或 -NH 基团，A 和 B 与 X 或 Y 意义相同，但不包括式 (II) 所示的基团，R'.R2、R3 和 R4 分别代表氢原子、卤素原子或含有 I 至 4 个碳原子的烷基，R5 和 R6 分别代表氢原子或含有 I 至 4 个碳原子的烷基，R7 和 R8 分别代表含有 I 至 4 个碳原子的烷基，或 R7 和 R8 与相邻的氮原子一起形成杂环，该杂环可选择性地含有另外的杂原子；及其酸加成盐。
• 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.