1-(2-chlorophenyl)-3-(furan-2-yl)prop-2-en-1-one | 338962-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-chlorophenyl)-3-(furan-2-yl)prop-2-en-1-one
• CAS: 338962-82-6
• 化学式: C₁₃H₉ClO₂
• 分子量: 232.666
• InChiKey: CJFXYIJZMOEFAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  邻氯苯乙酮 、 1-(2-chlorophenyl)-3-(furan-2-yl)prop-2-en-1-one 在 双(三环己基膦)二氯化钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以20%的产率得到9-(2-furyl)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione
  参考文献：
  名称：

  钯催化的1，5-二酮的直接分子内双α-C–H芳基化：Tröger碱类似物的合成策略

  摘要：

  9-Aryl-2,3：6,7-dibenzobicyclo [3.3.1] nona-2,6-diene-4,8-​​diones是通过容易获得的邻氯苯乙酮和邻氯查尔酮催化的串联反应直接制备的。 PdCl 2（PCy 3）2。

  DOI：

  10.1016/j.tetlet.2014.04.069
• 作为产物：
  描述：

  糠醛 、 邻氯苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以91%的产率得到1-(2-chlorophenyl)-3-(furan-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Potassium–Tertiary Butoxide–Assisted Addition of Thioglicolic Acid to Chalcone Derivatives Under Solvent-Free Conditions

  摘要：

  A series of chalcone derivatives containing thioglicolic acid (4a-j) was prepared by addition of thioglicolic acid to the chalcones (3a-j) in the presence of KOt-Bu under solvent-free conditions. The mechanistic pathway of the reaction can be explained by the Michael-type addition of thioglicolic acid to chalcone derivatives (3a-j).

  DOI：

  10.1080/00397910903291129

文献信息

• The synthesis and screening of the antimicrobial activity of some novel 3-(furan-2-yl)-1-(aryl)-3-(phenylthio) propan-1-one derivatives
  作者：Mustafa Ceylan、Meliha Burcu Gürdere、İsa Karaman、Hayreddin Gezegen

  DOI：10.1007/s00044-009-9279-4

  日期：2011.1

  addition of thiophenol to chalcones (1a–m) in the presence of a catalytic amount of KOt-Bu in solvent free conditions. In addition, the antibacterial and antifungal in vitro properties were tested against some human pathogenic microorganisms by employing the disk diffusion technique. A majority of compounds were remarkably active against several of the microorganisms. Compound 3i was determined to be the

  在无溶剂条件下，在催化量的KO t -Bu存在下，将硫代苯酚加到查耳酮（1a - m）中，制备了一系列苯硫酚加合物（3a - m）。此外，通过使用圆盘扩散技术测试了对某些人类病原微生物的抗菌和抗真菌体外性能。大多数化合物对几种微生物具有显着的活性。确定化合物3i是最具活性的化合物。
• Elaborating Complex Heteroaryl‐Containing Cycles via Enantioselective Palladium‐Catalyzed Cycloadditions
  作者：Barry M. Trost、Zhiwei Jiao、Chao‐I. (Joey) Hung

  DOI：10.1002/anie.201910061

  日期：2019.10.14

  asymmetric synthesis of heteroaryl-containing cycles via palladium-catalyzed cyclization is reported. Most classes of nitrogen-containing aromatics, including pyridines, quinolines, pyrimidines, various azoles and the derivatives of nucleobases are compatible substrates, offering various heteroaryl-substituted cyclopentane, pyrrolidine, furanidine and bicyclo[4.3.1]decadiene derivatives with good to

  报道了通过钯催化的环化反应不对称合成含杂芳基环的一般方法。多数种类的含氮芳族化合物，包括吡啶，喹啉，嘧啶，各种唑类和核碱基衍生物都是相容的底物，可提供各种杂芳基取代的环戊烷，吡咯烷，呋喃啶和双环[4.3.1]癸二烯衍生物，具有良好至优异的对映选择性和非对映选择性。
• Iodine-Catalyzed Addition of Methyl Thioglycolate to Chalcones
  作者：M. Burcu Gürdere、Hayreddin Gezegen、Yakup Budak、Mustafa Ceylan

  DOI：10.1080/10426507.2011.643435

  日期：2012.8.1

  A series of novel beta-mercapto carbonyl compounds (3a-z), methyl 2-(3-oxo-1,3-diarylpropylthio)acetate, were synthesized and characterized via iodine-catalyzed addition of methyl thioglycolate to chalcones (1a-z).
• Potassium–Tertiary Butoxide–Assisted Addition of Thioglicolic Acid to Chalcone Derivatives Under Solvent-Free Conditions
  作者：Mustafa Ceylan、Meliha Burcu Gürdere、Hayreddin Gezegen、Yakup Budak

  DOI：10.1080/00397910903291129

  日期：2010.8.5

  A series of chalcone derivatives containing thioglicolic acid (4a-j) was prepared by addition of thioglicolic acid to the chalcones (3a-j) in the presence of KOt-Bu under solvent-free conditions. The mechanistic pathway of the reaction can be explained by the Michael-type addition of thioglicolic acid to chalcone derivatives (3a-j).
• Palladium-catalyzed direct intramolecular double α-C–H arylation of 1,5-diketone: a strategy for synthesis of Tröger’s base analogues
  作者：Jia Ju、Lei Zhang、Ruimao Hua

  DOI：10.1016/j.tetlet.2014.04.069

  日期：2014.5

  9-Aryl-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-diones were straightforwardly prepared via a tandem reaction of easily available ortho-chloroacetophenone and ortho-chlorochalcone catalyzed by PdCl2(PCy3)2.

  9-Aryl-2,3：6,7-dibenzobicyclo [3.3.1] nona-2,6-diene-4,8-​​diones是通过容易获得的邻氯苯乙酮和邻氯查尔酮催化的串联反应直接制备的。 PdCl 2（PCy 3）2。