1-(5-甲基噻吩-2-基)-1-丁酮 | 79852-26-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(5-甲基噻吩-2-基)-1-丁酮
• 英文名称: 2-methyl-4-butyrylthiophene
• 英文别名: 1-(5-methylthiophen-2-yl)butan-1-one；1-(5-methyl-[2]thienyl)-butan-1-one；1-(5-Methyl-[2]thienyl)-butan-1-on
• CAS: 79852-26-9
• 化学式: C₉H₁₂OS
• mdl: MFCD02254119
• 分子量: 168.26
• InChiKey: GDOVKRSCOWPYAI-UHFFFAOYSA-N

物化性质

• 沸点：
  136-137 °C(Press: 13 Torr)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  1-(5-甲基噻吩-2-基)-1-丁酮 在 sodium hypochlorite 作用下， 生成 5-甲基-2-噻吩甲酸
  参考文献：
  名称：

  Condensations Effected by Boron Fluoride Complexes. III. The Acylation of Certain Substituted Thiophenes and Furans¹

  摘要：

  DOI：

  10.1021/ja01164a103
• 作为产物：
  描述：

  1-(5-methylthiophen-2-yl)butan-1-ol 在 copper dichloride 、 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt 叔丁基过氧化氢 、 四丁基氯化铵 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 以100%的产率得到1-(5-甲基噻吩-2-基)-1-丁酮
  参考文献：
  名称：

  一种新型高效水溶性铜络合物，用于叔丁基氢过氧化物氧化仲1-杂芳基醇

  摘要：

  由CuCl 2和2,2'-联喹啉-4,4'-二羧酸二钾盐（BQC）原位生成的水溶性铜络合物已被证明是一种高效且选择性的催化剂，可氧化次要1-在温和条件下，用叔丁基过氧化氢水溶液将杂芳基醇转变为相应的杂芳族酮。该催化体系与不同的杂环兼容，例如吡啶，吡咯，吲哚，噻吩，呋喃，噻唑和咪唑。

  DOI：

  10.1016/j.tetlet.2006.01.061

文献信息

• Synthesis and Characterization of AlCl₃ Impregnated Molybdenum Oxide as Heterogeneous Nano-Catalyst for the Friedel-Crafts Acylation Reaction in Ambient Condition
  作者：Arvind H. Jadhav、Amutha Chinnappan、Vishwanath Hiremath、Jeong Gil Seo

  DOI：10.1166/jnn.2015.11253

  日期：2015.10.1

  Aluminum trichloride (AlCl₃) impregnated molybdenum oxide heterogeneous nano-catalyst was prepared by using simple impregnation method. The prepared heterogeneous catalyst was characterized by powder X-ray diffraction, FT-IR spectroscopy, solid-state NMR spectroscopy, SEM imaging, and EDX mapping. The catalytic activity of this protocol was evaluated as heterogeneous catalyst for the Friedel-Crafts acylation reaction at room temperature. The impregnated MoO₄(AlCl₂)₂ catalyst showed tremendous catalytic activity in Friedel-Crafts acylation reaction under solvent-free and mild reaction condition. As a result, 84.0% yield of acyl product with 100% consumption of reactants in 18 h reaction time at room temperature was achieved. The effects of different solvents system with MoO₄(AlCl₂)₂ catalyst in acylation reaction was also investigated. By using optimized reaction condition various acylated derivatives were prepared. In addition, the catalyst was separated by simple filtration process after the reaction and reused several times. Therefore, heterogeneous MoO₄(AlCl₂)₂ catalyst was found environmentally benign catalyst, very convenient, high yielding, and clean method for the Friedel-Crafts acylation reaction under solvent-free and ambient reaction condition.

  氯化铝（AlCl3）浸渍的钼氧化物非均相纳米催化剂是通过简单的浸渍方法制备的。所制备的非均相催化剂通过粉末X射线衍射、傅里叶变换红外光谱、固体核磁共振光谱、扫描电镜成像和能谱分析进行了表征。该方法的催化活性被评估为在室温下作为弗里德尔-克拉夫茨酰化反应的非均相催化剂。浸渍的MoO4(AlCl2)2催化剂在无溶剂和温和反应条件下表现出巨大的催化活性。结果表明，在室温下，18小时反应时间内，酰基产物的产率为84.0％，反应物的消耗率为100％。还研究了在酰化反应中使用MoO4(AlCl2)2催化剂的不同溶剂体系的影响。通过使用优化的反应条件，制备了各种酰化衍生物。此外，反应后通过简单的过滤过程分离催化剂，并多次重复使用。因此，非均相MoO4(AlCl2)2催化剂被发现是一种环境友好的催化剂，非常方便，产率高，是一种无溶剂和环境条件下进行弗里德尔-克拉夫茨酰化反应的清洁方法。
• Iodine promoted α-hydroxylation of ketones
  作者：Yogesh Siddaraju、Kandikere Ramaiah Prabhu

  DOI：10.1039/c5ob00684h

  日期：——

  A novel method for α-hydroxylation of ketones using substoichiometric amount of iodine under metal-free conditions is described.

  描述了一种在无金属条件下使用亚化学计量量的碘对酮进行α-羟基化的新方法。

• Convenient synthesis of aryl-substituted halo olefins from aromatic ketones and acetyl halides in the presence of silica gel-supported zinc halides
  作者：Mitsuo Kodomari、Takashi Nagaoka、Yuhsuke Furusawa

  DOI：10.1016/s0040-4039(01)00378-1

  日期：2001.4

  A simple and efficient procedure has been developed for the synthesis of aryl-substituted chloro and bromo olefins from aromatic ketones and acetyl halides in the presence of silica gel-supported zinc halides. The Z-isomer is selectively formed.

  已经开发了一种简单有效的方法，可在硅胶负载的卤化锌存在下，由芳族酮和乙酰卤化物合成芳基取代的氯代和溴代烯烃。所述ž选择性地形成-异构体。
• THE BIRCH REDUCTION OF 2-ACYLTHIOPHENES. SYNTHESIS OF 1,3-DIENYL KETONES FROM 2-ACYLTHIOPHENES
  作者：Kimihiko Kosugi、Alexander V. Anisimov、Hiroshi Yamamoto、Ryuichi Yamashiro、Kozo Shirai、Takanobu Kumamoto

  DOI：10.1246/cl.1981.1341

  日期：1981.10.5

  The Birch reduction of 2-acyl or 2-acyl-5-alkylthiophenes and subsequent alkylation by alkyl halides gave 2-acyl-2-alkyl or 2-acyl-2,5-dialkyl-2,5-dihydrothiophenes in good yields. Further, 1,3-dienyl ketones were obtained in good yields by the thermolysis of 2,5-dihydrothiophene 1,1-dioxides which were obtained by the oxidation of resulted dihydrothiophene derivatives with m-chloroperbenzoic acid

  2-酰基或 2-酰基-5-烷基噻吩的 Birch 还原和随后的烷基卤化物烷基化以良好的产率得到 2-酰基-2-烷基或 2-酰基-2,5-二烷基-2,5-二氢噻吩。此外，通过将所得二氢噻吩衍生物与间氯过苯甲酸氧化而获得的 2,5-二氢噻吩 1,1-二氧化物的热解，以良好的收率获得了 1,3-二烯基酮。
• FIVE-MEMBERED HETEROCYCLIC OXOCARBOXYLIC ACID COMPOUND AND MEDICAL USE THEREOF
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP4053124A1

  公开（公告）日：2022-09-07

  The present invention relates to a five-membered heterocyclic oxocarboxylic acid compound and the medical use thereof. Specifically, the present invention relates to a compound as represented by formula (I) and a pharmaceutically acceptable salt, prodrug, hydrate, solvate or crystal form thereof, and also relates to a method for preparing the compound, a pharmaceutical composition containing the compound, and the medical use thereof as a secretion regulator of type I interferon, especially as a STING agonist, and in the preparation of a drug for preventing and/or treating diseases related to type I interferon.

  本发明涉及一种五元杂环氧化羧酸化合物及其医疗用途。具体地说，本发明涉及一种由式（I）表示的化合物及其药学上可接受的盐、原药、水合物、溶液或晶体形式，还涉及一种制备该化合物的方法、一种含有该化合物的药物组合物，以及其作为 I 型干扰素分泌调节剂，特别是作为 STING 激动剂，以及在制备预防和/或治疗与 I 型干扰素相关疾病的药物中的医学用途。