4-isobutyl-2-formylthiophene | 957206-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-isobutyl-2-formylthiophene
• 英文别名: 4-(2-methylpropyl)-2-thiophenecarbaldehyde；4-isobutylthiophene-2-carbaldehyde；4-(2-methylpropyl)thiophene-2-carbaldehyde
• CAS: 957206-05-2
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: NNABFQORHXSFGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  3
• 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：

  溶剂黄146 、 4-isobutyl-2-formylthiophene 、 N-碘代丁二酰亚胺 、 在 silica gel 、 title compound 作用下， 以 氯仿 为溶剂， 反应 9.0h， 生成 5-Iodo-4-isobutylthiophene-2-carbaldehyde
  参考文献：
  名称：

  HETEROARYLAMIDE LOWER CARBOXYLIC ACID DERIVATIVE

  摘要：

  提供一种新型化合物，具有S1P受体激动活性，表现出优异的免疫抑制效果，产生较少的不良副作用，并可口服。本发明提供一种由通式（I）表示的化合物（其中A是单键，-O-或-CH2-；R1表示氢原子或C1-C6烷基基团，V表示从以下组（1）至（3）中选择的任一组：（1）-G1-，（2）-G2-N（R2）-G3-，以及（3）由式2表示的组，其中Z1和Z2分别表示氢原子或C1-C6烷基基团，Z3表示氢或类似物，Q表示-CH2-O-或类似物，Y表示由式3表示的基团，其盐或溶剂化物。

  公开号：

  US20090324581A1
• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 、 异丁基硼酸 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， 生成 4-isobutyl-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。
• 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