2-acetyl-4-methylbenzo[b]thiophene | 1467-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-acetyl-4-methylbenzo[b]thiophene
• 英文别名: 2-Acetyl-4-methylbenzo(b)thiophene；1-(4-methyl-1-benzothiophen-2-yl)ethanone
• CAS: 1467-88-5
• 化学式: C₁₁H₁₀OS
• 分子量: 190.266
• InChiKey: JWDNVFPOFKNDEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-Methylmercapto-6-methyl-benzaldehyd 、 一氯丙酮 在 magnesium oxide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以95.7%的产率得到2-acetyl-4-methylbenzo[b]thiophene
  参考文献：
  名称：

  Investigation on the One-Step Preparation of 2-Substituted Benzo[B]Thiophenes

  摘要：

  A convenient and efficient synthesis of 2-substituted benzo[b]thiophenes is described. This one-step reaction of alkylthiobenzaldehyde and activated electrophiles proceeded smoothly in toluene at 120 degrees C with magnesium oxide as a catalyst. The target 2-substituted benzo[b]thiophenes are obtained in moderate yields and the side reaction is inhibited via azeotropic distillation. According to the experiments, a plausible mechanism is presented.

  DOI：

  10.1080/10426507.2012.717140

文献信息

• Efficient Method for Synthesis of 2-Acetylbenzo(b)thiophene and Its Derivatives, the Key Synthons for 5-Lipoxygenase Inhibitors
  作者：Sanjay R. Chemburkar、David G. Anderson、Rajarathnam E. Reddy

  DOI：10.1080/00397910903162775

  日期：2010.6.16

  tert-butylmercaptan (6) to form 2-(tert-butylthio)benzaldehyde (7a), which upon treatment with HBr in water gave the disulfide derivative 2,2′-disulfanediyldibenzaldehyde (8a) in 97% yield. Finally, the reaction of 8a with acetylacetone (9) and 1-chloroacetone (10) gave 2-acetylbenzo(b)thiophene (2a) in 94% yield. The methodology is general and suitable for the preparation of its derivatives, 2b–d.

  开发了一种有效的方法来合成 2-乙酰苯并 (b) 噻吩 (2a)，这是齐留通 (1) 的关键中间体。合成包括用叔丁硫醇 (6) 处理 2-氯苯甲醛 (5a) 以形成 2-(叔丁硫基) 苯甲醛 (7a)，在水中用 HBr 处理后得到二硫化物衍生物 2,2'-二硫烷二基二苯甲醛 (8a) ) 的产率为 97%。最后，8a 与乙酰丙酮 (9) 和 1-氯丙酮 (10) 的反应以 94% 的产率得到 2-乙酰苯并 (b) 噻吩 (2a)。该方法是通用的，适用于其衍生物 2b-d 的制备。
• Investigation on the One-Step Preparation of 2-Substituted Benzo[B]Thiophenes
  作者：Qian Zhao、Chao Qian、Xin-Zhi Chen

  DOI：10.1080/10426507.2012.717140

  日期：2013.7.1

  A convenient and efficient synthesis of 2-substituted benzo[b]thiophenes is described. This one-step reaction of alkylthiobenzaldehyde and activated electrophiles proceeded smoothly in toluene at 120 degrees C with magnesium oxide as a catalyst. The target 2-substituted benzo[b]thiophenes are obtained in moderate yields and the side reaction is inhibited via azeotropic distillation. According to the experiments, a plausible mechanism is presented.

表征谱图