3-cyano-6-(4-chlorophenyl)-4-[bis(4-fluorophenyl)piperazino]-2H-pyran-2-one | 388573-74-8

• 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: 3-cyano-6-(4-chlorophenyl)-4-[bis(4-fluorophenyl)piperazino]-2H-pyran-2-one
• 英文别名: 4-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]-6-(4-chlorophenyl)-2-oxopyran-3-carbonitrile
• CAS: 388573-74-8
• 化学式: C₂₉H₂₂ClF₂N₃O₂
• 分子量: 517.962
• InChiKey: JZPQWWXQGFUQPN-UHFFFAOYSA-N

物化性质

• 沸点：
  588.7±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-cyano-6-(4-chlorophenyl)-4-[bis(4-fluorophenyl)piperazino]-2H-pyran-2-one 在 吡啶 、 ammonium carbonate 作用下， 以43%的产率得到4-{4-[bis(4-fluorophenyl)methyl]-1-piperazinyl}-6-(4-chlorophenyl)-2-pyridinamine
  参考文献：
  名称：

  Synthesis of Aminonicotinonitriles and Diaminopyridines through Base-Catalyzed Ring Transformation of 2H-Pyran-2-ones

  摘要：

  An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.

  DOI：

  10.1021/jo0204496
• 作为产物：
  描述：

  6-(4-chlorophenyl)-3-cyano-4-methylsulfanyl-2H-pyran-2-one 、 4,4'-二氟苯甲哌嗪 生成 3-cyano-6-(4-chlorophenyl)-4-[bis(4-fluorophenyl)piperazino]-2H-pyran-2-one
  参考文献：
  名称：

  通过适当的官能化2 H-吡喃-2-酮，通过环转化反应，由碳离子诱导的碱催化合成不对称联芳基

  摘要：

  由碳芳基引起的6-芳基-4-甲基硫烷基-2 H-吡喃-2-基的碳负离子诱导的环化描述并说明了不对称的高度官能化的联芳基的合成，该氨基取代基与一个苯环中的两个腈基并置。1-3-甲腈（1）和4 - sec-氨基-6-芳基-2 H-吡喃-2-one-3-腈（2）变成2-氨基-4-芳基-6-甲基硫烷基-1,3 -使用苯丙二腈作为碳负离子源的2-苯并二腈（3）和2-氨基-6-仲-氨基-4-芳基-1,3-苯并二腈（4），产率中等。

  DOI：

  10.1016/s0040-4039(01)01481-2

文献信息

• One-pot synthesis of unsymmetrical biaryls from suitably functionalized 2H-pyran-2-ones through carbanion-induced ring-transformation reactions
  作者：Vishnu J. Ram、Pratibha Srivastava、Nidhi Agarwal、Ashoke Sharon、Prakas R. Maulik

  DOI：10.1039/b009725j

  日期：——

  An innovative synthesis of unsymmetrical biaryls (2,6) with electron-acceptor and electron-donor substituents through carbanion-induced C–C bond formation from 6-aryl-3-cyano-4-methylthio-2H-pyran-2-ones (1) and 4-sec-amino-6-aryl-2H-pyran-2-ones (5), using aliphatic ketones as a source of carbanion, is delineated and illustrated. However, a reaction of pyran-2-ones (1) with aromatic ketones failed to yield any desired product and in lieu a new compound isolated was characterized as the corresponding (4,6-diarylpyran-2-ylidene)acetonitrile (3). The structure of two representative compounds 5h and 6q has been confirmed by single-crystal X-ray diffraction analysis.

  一种创新的非对称双联苯（2,6）合成方法，通过碳负离子引发的C-C键形成，将电子受体和电子供体取代基引入6-苯基-3-氰基-4-甲硫基-2H-吡喃-2-酮（1）和4-二级氨基-6-苯基-2H-吡喃-2-酮（5），并使用脂肪酮作为碳负离子源，该方法得到了详细阐述和图解。然而，吡喃-2-酮（1）与芳香酮的反应未能产生预期产物，反而分离出一种新化合物，其特征为相应的（4,6-二苯基吡喃-2-亚基）乙腈（3）。通过单晶X射线衍射分析，两个代表性化合物5h和6q的结构得到了确认。
• Carbanion-induced base-catalyzed synthesis of unsymmetrical biaryls from suitably functionalized 2H-pyran-2-ones through ring-transformation reactions
  作者：Vishnu Ji Ram、Nidhi Agarwal

  DOI：10.1016/s0040-4039(01)01481-2

  日期：2001.10

  of unsymmetrical highly functionalized biaryls with an amino substituent juxtaposed with two nitrile groups in one of the phenyl rings is delineated and illustrated by the carbanion-induced ring-transformation of 6-aryl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitrile (1) and 4-sec-amino-6-aryl-2H-pyran-2-one-3-carbonitrile (2) to 2-amino-4-aryl-6-methylsulfanyl-1,3-benzodinitrile (3) and 2-amino-6-sec-amino-4-aryl-1

  由碳芳基引起的6-芳基-4-甲基硫烷基-2 H-吡喃-2-基的碳负离子诱导的环化描述并说明了不对称的高度官能化的联芳基的合成，该氨基取代基与一个苯环中的两个腈基并置。1-3-甲腈（1）和4 - sec-氨基-6-芳基-2 H-吡喃-2-one-3-腈（2）变成2-氨基-4-芳基-6-甲基硫烷基-1,3 -使用苯丙二腈作为碳负离子源的2-苯并二腈（3）和2-氨基-6-仲-氨基-4-芳基-1,3-苯并二腈（4），产率中等。
• Synthesis of Aminonicotinonitriles and Diaminopyridines through Base-Catalyzed Ring Transformation of 2<i>H</i>-Pyran-2-ones
  作者：Farhanullah、Nidhi Agarwal、Atul Goel、Vishnu Ji Ram

  DOI：10.1021/jo0204496

  日期：2003.4.1

  An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.
• A diversity oriented synthesis of highly functionalized unsymmetrical biaryls through carbanion induced ring transformation of 2H-pyran-2-ones
  作者：Nidhi Agarwal、Abhishek S Saxena、Farhanullah、Atul Goel、Vishnu J Ram

  DOI：10.1016/s0040-4020(02)01066-9

  日期：2002.10

  A new route for the synthesis of unsymmetrical biaryls endowed with electron withdrawing and donating substituents is delineated through base catalyzed ring transformation of 2H-pyran-2-ones with malononitrile in a single step. This procedure offers the flexibility of introducing desired functionalities in aromatic rings, which are difficult to obtain by other classical routes. (C) 2002 Elsevier Science Ltd. All rights reserved.