3-phenyl-5-piperidin-1-yl-2,3-dihydrofuran-4-carbonitrile | 203569-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-phenyl-5-piperidin-1-yl-2,3-dihydrofuran-4-carbonitrile
• CAS: 203569-66-8
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: KCBBJBYWELIYGH-UHFFFAOYSA-N

物化性质

• 沸点：
  399.3±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.26
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-5-piperidin-1-yl-2,3-dihydrofuran-4-carbonitrile 在 dirhodium tetraacetate 溶剂黄146 作用下， 以 氟苯 、 丙酮 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Synthesis of 1,3-Oxazines and Furo[2,3-b]pyrans by reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with dibenzoyldiazomethanes

  摘要：

  2-Amino-4,5-dihydro-3-furancarbonitriles (1) react with a slight excess of dibenzoyldiazomethane in the presence of rhodium(II) acetate to give 1,3-oxazin-4-ones (2). With three equivalents of dibenzoyldiazomethane compounds 1 react to afford furo[2,3-b]pyran-3a-carbonitriles (3). Compound 3a was also obtained by treatment of 2a with two equivalents of dibenzoyldiazomethane.

  DOI：

  10.1002/prac.19983400108
• 作为产物：
  描述：

  哌啶 、 5-氨基-3-苯基-2,3-二氢呋喃-4-甲腈 在 三甲胺盐酸盐 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以78%的产率得到3-phenyl-5-piperidin-1-yl-2,3-dihydrofuran-4-carbonitrile
  参考文献：
  名称：

  Synthesis of 1,3-Oxazines and Furo[2,3-b]pyrans by reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with dibenzoyldiazomethanes

  摘要：

  2-Amino-4,5-dihydro-3-furancarbonitriles (1) react with a slight excess of dibenzoyldiazomethane in the presence of rhodium(II) acetate to give 1,3-oxazin-4-ones (2). With three equivalents of dibenzoyldiazomethane compounds 1 react to afford furo[2,3-b]pyran-3a-carbonitriles (3). Compound 3a was also obtained by treatment of 2a with two equivalents of dibenzoyldiazomethane.

  DOI：

  10.1002/prac.19983400108

文献信息

• Synthesis of N,N-Disubstituted 1-Cyanocyclopropanecarboxamides
  作者：Kenji Yamagata、Fumi Okabe、Yoshinobu Tagawa

  DOI：10.1002/ejoc.200200516

  日期：2003.7

  amino)-4,5-dihydro-3-furancarbonitriles 1a−i reacted with acetyl chloride to yield the corresponding ring-opening products 2a−i. The cyclization of compounds 2a−f with bases gave the corresponding N,N-disubstituted 1-cyanocyclopropanecarboxamides 3a−c and (E)-1-cyano-2-phenylcyclopropanecarboxamides 3d−f. The same compounds 3d−f were also obtained by treatment of compounds 2g−i with sodium methoxide. (©

  2-(双取代氨基)-4,5-二氢-3-呋喃甲腈 1a-i 与乙酰氯反应生成相应的开环产物 2a-i。化合物 2a-f 与碱的环化得到相应的 N,N-二取代 1-氰基环丙烷甲酰胺 3a-c 和 (E)-1-氰基-2-苯基环丙烷甲酰胺 3d-f。通过用甲醇钠处理化合物2g-i也获得了相同的化合物3d-f。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis of Dihydrooxepins by the Cycloaddition of 2-Amino-4,5-dihydro-3-furancarbonitriles with Dimethyl Acetylenedicarboxylate
  作者：Hiroshi Maruoka、Fumi Okabe、Eiichi Masumoto、Toshihiro Fujioka、Kenji Yamagata

  DOI：10.3987/com-13-12819

  日期：——

  A facile and efficient synthesis of dihydrooxepins is described. Treatment of readily available 2-amino-4,5-dihydro-3-furancarbonitriles with dimethyl acetylenedicarboxylate at room temperature caused smoothly a cycloaddition reaction, followed by a ring expansion, giving the corresponding dihydrooxepin derivatives.