3-(4-chlorophenyl)-1-(thiophen-3-yl)prop-2-en-1-one | 144080-41-1

• 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: 3-(4-chlorophenyl)-1-(thiophen-3-yl)prop-2-en-1-one
• 英文别名: 3-(4-Chlorophenyl)-1-(3-thienyl)-prop-2-en-1-one；3-(4-chlorophenyl)-1-thiophen-3-ylprop-2-en-1-one
• CAS: 144080-41-1
• 化学式: C₁₃H₉ClOS
• 分子量: 248.733
• InChiKey: JKQOPBWIBGXMBR-UHFFFAOYSA-N

物化性质

• 沸点：
  390.5±42.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-(4-chlorophenyl)-1-(thiophen-3-yl)prop-2-en-1-one 在 三乙基硅烷 、 [((R,R,S,S)-Duanphos)Rh(nbd)][BF₄] 、 三乙胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 二氯甲烷 、 氯仿 、 水 、 甲苯 为溶剂， 反应 26.25h， 生成 ((2S,4R)-4-(4-chlorophenyl)-2-(thiophen-3-yl)-3,4-dihydroquinolin-1(2H)-yl)(3,5-dinitrophenyl)methanone
  参考文献：
  名称：

  A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines

  摘要：

  Rh催化的2-氨基苯硼酸衍生物的共轭加成被用于四氢喹啉的对映选择性和不对称合成。

  DOI：

  10.1039/c4cc04940c
• 作为产物：
  描述：

  3-乙酰基噻吩 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(4-chlorophenyl)-1-(thiophen-3-yl)prop-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

• Convergent, Regiospecific Synthesis of Quinolines from <i>o</i>-Aminophenylboronates
  作者：Joachim Horn、Stephen P. Marsden、Adam Nelson、David House、Gordon G. Weingarten

  DOI：10.1021/ol8016726

  日期：2008.9.18

  A direct convergent two-component synthesis of quinolines from alpha,beta-unsaturated ketones and o-aminophenylboronic acid derivatives is reported. The reaction is regiocomplementary to the traditional Skraup-Doebner-Von Miller synthesis and proceeds under basic rather than strongly acidic conditions. Quinolines substituted in the benzenoid ring can be accessed by using substituted o-aminophenylboronates

  据报道由α，β-不饱和酮和邻氨基苯基硼酸衍生物直接会聚两组分合成喹啉。该反应与传统的Skraup-Doebner-Von Miller合成在区域上互补，并且在碱性而不是强酸性条件下进行。苯环中取代的喹啉可以通过使用取代的邻氨基苯硼酸酯来获得，该邻氨基苯硼酸酯是通过钯催化相应邻溴代苯胺的直接硼化反应制得的。
• 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。
• PREHEATED FLY-ASH CATALYZED ALDOL CONDENSATION: EFFICIENT SYNTHESIS OF CHALCONES AND ANTIMICROBIAL ACTIVITIES OF SOME 3-THIENYL CHALCONES
  作者：RANGANATHAN ARULKUMARAN、SAMBANDHAMOORTHY VIJAYAKUMAR、S PAZHANIVEL SAKTHINATHAN、DAKSHNAMOORTHY KAMALAKKANNAN、KALIYAPERUMAL RANGANATHAN、RAMAMOORTHY SURESH、RAJASEKARAN SUNDARARAJAN、GANESAN VANANGAMUDI、GANESAMOORTHY THIRUNARAYANAN

  DOI：10.4067/s0717-97072013000200008

  日期：——
• 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：——
• 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.]