4,5-二氢-2-(1-哌啶基)-3-呋喃甲腈 | 203569-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4,5-二氢-2-(1-哌啶基)-3-呋喃甲腈
• 英文名称: 4,5-dihydro-2-(1-piperidinyl)-3-furancarbonitrile
• 英文别名: 4,5-dihydro-2-piperidino-3-furancarbonitrile；5-Piperidin-1-yl-2,3-dihydrofuran-4-carbonitrile
• CAS: 203569-63-5
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: RGHDVYLBQOKERO-UHFFFAOYSA-N

物化性质

• 沸点：
  288.9±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-二氢-2-(1-哌啶基)-3-呋喃甲腈 在 dirhodium tetraacetate 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氟苯 、 苯 为溶剂， 反应 5.0h， 生成 dimethyl (4-cyano-5-piperidino-(2H)-furan-3-ylidene)propanedioate
  参考文献：
  名称：

  Rhodium(II) acetate-catalyzed reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with dialkyl diazomalonates

  摘要：

  DOI：

  10.1002/(sici)1521-3897(199908)341:6<562::aid-prac562>3.0.co;2-4
• 作为产物：
  描述：

  哌啶 、 5-氨基-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 1.0h， 以66%的产率得到4,5-二氢-2-(1-哌啶基)-3-呋喃甲腈
  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)
• Ring‐Opening Reaction of 2‐Amino‐4,5‐dihydro‐3‐furancarbonitriles with Carboxylic Acids under Solvent‐Free Conditions
  作者：Hiroshi Maruoka、Fumi Okabe、Kenji Yamagata

  DOI：10.1080/00397910701797848

  日期：2008.1.1

  5‐dihydro‐3‐furancarbonitriles is described. Thermal treatment of 4,5‐dihydro‐2‐(4‐morpholinyl, 1‐piperidinyl, and 1‐pyrrolidinyl)‐3‐furancarbonitriles with various carboxylic acids in the absence of solvent caused a ring‐opening reaction to give the corresponding 2‐cyanobutanamide derivatives.

  摘要描述了以 2-氨基-4,5-二氢-3-呋喃甲腈为原料制备 2-氰基丁酰胺衍生物的新方法。4,5-二氢-2-(4-吗啉基、1-哌啶基和1-吡咯烷基)-3-呋喃甲腈在无溶剂下与各种羧酸进行热处理引起开环反应，得到相应的2-氰基丁酰胺衍生物。
• One‐Pot Synthesis of Tetrahydro‐2‐Methylidenefurans
  作者：Fumi Okabe、Yoshinobu Tagawa、Kenji Yamagata

  DOI：10.1081/scc-200054188

  日期：2005.4.1

  Tetrahydro-2-methylidenefurans were prepared by the ring-opening/ recyclization reaction of 2-(disubstituted amino)-4,5-dihydro-3-furancarbonitriles with dichloroacetyl chloride in the presence of potassium carbonate.
• 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.
• Synthesis of 1,3-Oxazines and Furo[2,3-b]pyrans by reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with dibenzoyldiazomethanes
  作者：Kenji Yamagata、Keiko Akizuki、Motoyoshi Yamazaki

  DOI：10.1002/prac.19983400108

  日期：——

  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.