1-(thiophen-3-yl)-3-m-tolylprop-2-en-1-one | 1245505-00-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(thiophen-3-yl)-3-m-tolylprop-2-en-1-one
• 英文别名: 3-(3-Methylphenyl)-1-thiophen-3-ylprop-2-en-1-one；3-(3-methylphenyl)-1-thiophen-3-ylprop-2-en-1-one
• CAS: 1245505-00-3
• 化学式: C₁₄H₁₂OS
• 分子量: 228.315
• InChiKey: YHDUEVFHFFKWCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-(thiophen-3-yl)-3-m-tolylprop-2-en-1-one 、 环戊酮 在 苄基三乙基氯化铵 、 potassium hydroxide 作用下， 以85%的产率得到2-(3-oxo-3-(thiophen-3-yl)-1-(m-tolyl)propyl)cyclopentanone
  参考文献：
  名称：

  Synthesis and Characterization of Some Novel Multisubstituted 6,7-Dihydro-5H-cyclopenta[b]pyridine Derivatives

  摘要：

  In this study, we describe systematic preparation of a series of aryl-substituted pyridine derivatives. The 1,5-dicarbonyls (3a-i) were prepared in the solvent-free conditions starting from chalcone derivatives (1a-i). The target compounds, 4-aryl-2-(thiophen-3-yl)-6,7-dihydro-5H-cyclopenta[b]-pyridine derivatives (5a-i), were synthesized by a cyclization reaction of the 1,5-dicarbonyls (3a-i) with ammonium acetate (NH4OAc) in acetic acid. The characterization of synthesized compounds was proved by elemental analyses, infrared, mass spectrometry, and H-1 and C-13 NMR spectroscopy. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.840004
• 作为产物：
  描述：

  3-乙酰基噻吩 、 3-甲基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(thiophen-3-yl)-3-m-tolylprop-2-en-1-one
  参考文献：
  名称：

  Unexpected lactonization accompanying addition of ethyl acetoacetate to chalcones derived from 3-acetylthiophene

  摘要：

  含有噻吩环的查尔酮衍生物通过3-乙酰基噻吩与芳香醛的缩合反应制备，产率优异。在固体NaOH存在的CH2Cl2中，将乙酰乙酸乙酯加入查尔酮衍生物3a-3h中，结果形成了双环内酯衍生物5a-5h和6-(乙氧羰基)环己烯酮衍生物6a-6h的混合物。

  DOI：

  10.1135/cccc2010150

文献信息

• Potassium tert-Butoxide Catalyzed Synthesis and Characterization of Novel 3-Aryl-3-(phenylthio)-1-(thiophen-3-yl)propan-1-one Derivatives
  作者：Yakup Budak

  DOI：10.1002/cjoc.201180484

  日期：2012.2

  series of thiophenyl‐containing 3‐thiophene derivatives (4a–4i) were prepared via the reaction of chalcone‐analogua compounds (3a–3i) and thiophenol in the presence of catalytic amount of KOBu‐t in CH2Cl2 with moderate to high yields. The mechanistic pathway of the reaction was explained by the Michael‐type addition of thiophenol to chalcone derivatives (3a–3i).

  含有噻吩基-3-噻吩衍生物（一系列4A - 4I）经查耳酮类化合物analogua（反应制备3A - 3I和苯硫酚在KOBu-催化量的存在下）吨在CH 2氯2至中度高产。该反应的机理途径是通过在查尔酮衍生物（3a - 3i）中将苯酚的Michael型加成来解释的。
• Budak, Yakup; Burcu Guerdere; Kececi, Meryem, Bulletin of the Chemical Society of Ethiopia, 2010, vol. 24, # 1, p. 85 - 91
  作者：Budak, Yakup、Burcu Guerdere、Kececi, Meryem、Ceylan, Mustafa

  DOI：——

  日期：——
• Unexpected lactonization accompanying addition of ethyl acetoacetate to chalcones derived from 3-acetylthiophene
  作者：Yakup Budak、Esra Findik

  DOI：10.1135/cccc2010150

  日期：——

  Chalcone derivatives containing thiophene ring were prepared by the condensation of 3-acetylthiophene with aromatic aldehydes in excellent yields. The addition of ethyl acetoacetate to chalcone derivatives 3a–3h in the presence of solid NaOH in CH₂Cl₂ resulted in the formation of the mixture of bicyclic lactone derivatives 5a–5h and 6-(ethoxycarbonyl)cyclohexenone derivatives 6a–6h.

  含有噻吩环的查尔酮衍生物通过3-乙酰基噻吩与芳香醛的缩合反应制备，产率优异。在固体NaOH存在的CH2Cl2中，将乙酰乙酸乙酯加入查尔酮衍生物3a-3h中，结果形成了双环内酯衍生物5a-5h和6-(乙氧羰基)环己烯酮衍生物6a-6h的混合物。
• Synthesis and Characterization of Some Novel Multisubstituted 6,7-Dihydro-5<i>H</i>-cyclopenta[<i>b</i>]pyridine Derivatives
  作者：Meliha Burcu Gürdere、Burhan Yilmaz、Yakup Budak

  DOI：10.1080/00397911.2013.840004

  日期：2014.4.3

  In this study, we describe systematic preparation of a series of aryl-substituted pyridine derivatives. The 1,5-dicarbonyls (3a-i) were prepared in the solvent-free conditions starting from chalcone derivatives (1a-i). The target compounds, 4-aryl-2-(thiophen-3-yl)-6,7-dihydro-5H-cyclopenta[b]-pyridine derivatives (5a-i), were synthesized by a cyclization reaction of the 1,5-dicarbonyls (3a-i) with ammonium acetate (NH4OAc) in acetic acid. The characterization of synthesized compounds was proved by elemental analyses, infrared, mass spectrometry, and H-1 and C-13 NMR spectroscopy. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]