4-氯-1-(3-甲基-2-噻吩基)-1-丁酮 | 157925-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-氯-1-(3-甲基-2-噻吩基)-1-丁酮
• 英文名称: 4-chloro-β-methyl-butyrothienone
• 英文别名: 4-Chloro-1-(3-methylthiophen-2-yl)butan-1-one
• CAS: 157925-24-1
• 化学式: C₉H₁₁ClOS
• 分子量: 202.705
• InChiKey: BHDFZLRXPWTDAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.8±32.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 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：

  4-氯-1-(3-甲基-2-噻吩基)-1-丁酮 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 二丁醚 、 水 、 异丙醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor tiagabine

  摘要：

  (R)-1-(4-(2,5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl)butyl)-3- piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2-bromo-3-methylthiophene 3. Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane. An alternative approach involving acylation of 2-lithio-3-methylthiophene 17a was found less satisfying. A metalloporphyrin assisted hydroxylation of tiagabine 1 also yielded the target metabolite. The structure of 5-hydroxytiagabine was confirmed by NMR-data including COSY, ROESY, HMQC and HMBC experiments.

  DOI：

  10.1016/s0040-4020(01)85345-x
• 作为产物：
  描述：

  2-溴-3-甲基噻吩 在 oxonium 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-氯-1-(3-甲基-2-噻吩基)-1-丁酮
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor tiagabine

  摘要：

  (R)-1-(4-(2,5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl)butyl)-3- piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2-bromo-3-methylthiophene 3. Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane. An alternative approach involving acylation of 2-lithio-3-methylthiophene 17a was found less satisfying. A metalloporphyrin assisted hydroxylation of tiagabine 1 also yielded the target metabolite. The structure of 5-hydroxytiagabine was confirmed by NMR-data including COSY, ROESY, HMQC and HMBC experiments.

  DOI：

  10.1016/s0040-4020(01)85345-x

文献信息

• Synthesis and biological studies of some novel antiinflammatory aryl-hydroxy-amino-ketones
  作者：D Hadjipavlou-Litina、E Rekka、L Hadjipetrou-Kourounakis、P Kourounakis

  DOI：10.1016/0223-5234(91)90216-a

  日期：1991.1

  The synthesis of some 4-hydroxy-(or amino)-ethyl-amino butyrophenones or butyrothienones is described. The interconversion of these compounds to the corresponding 5-aryl-4-oxa-1-azabicyclo[3,3,0]octanes is presented. The title compounds demonstrated good antiinflammatory activity in the adjuvant induced disease model. They also possessed antinociceptive, immuno-modulating and antioxidant activity, properties which are probably involved in the mechanism of their action.
• HADJIPAVLOU-LITINA, D.;REKKA, E.;HADJIPETROU-KOUROUNAKIS, L.;KOUROUNAKIS,+, EUR. J. MED. CHEM., 26,(1991) N, C. 85-90
  作者：HADJIPAVLOU-LITINA, D.、REKKA, E.、HADJIPETROU-KOUROUNAKIS, L.、KOUROUNAKIS,+

  DOI：——

  日期：——
• The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor tiagabine
  作者：Knud E. Andersen、Mikael Begtrup、Mukund S. Chorghade、Elaine C. Lee、Jesper Lau、Behrend F. Lundt、Hans Petersen、Per O. Sørensen、Henning Thøgersen

  DOI：10.1016/s0040-4020(01)85345-x

  日期：1994.1

  (R)-1-(4-(2,5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl)butyl)-3- piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2-bromo-3-methylthiophene 3. Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane. An alternative approach involving acylation of 2-lithio-3-methylthiophene 17a was found less satisfying. A metalloporphyrin assisted hydroxylation of tiagabine 1 also yielded the target metabolite. The structure of 5-hydroxytiagabine was confirmed by NMR-data including COSY, ROESY, HMQC and HMBC experiments.