2-(2-cyanoethyl)cyclopentanone oxime | 139908-27-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-cyanoethyl)cyclopentanone oxime
• 英文别名: 3-(2-Hydroxyiminocyclopentyl)propanenitrile；3-(2-hydroxyiminocyclopentyl)propanenitrile
• CAS: 139908-27-3
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: YRZYQJLOZCSOSA-UHFFFAOYSA-N

物化性质

• 沸点：
  338.2±15.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-cyanoethyl)cyclopentanone oxime 在 二氯化二硫 、 N,N-二异丙基乙胺 、 lithium sulfide 作用下， 以 四氢呋喃 为溶剂， 反应 80.0h， 以30%的产率得到3-(2,3,4,5,6,7,8-Heptathia-1-aza-cyclopenta[a]azulen-9-yl)-propionitrile
  参考文献：
  名称：

  一种新的肟对戊噻吩级联反应

  摘要：

  一个广泛的多米诺序列，包括一个乙烯基硫辅助的贝克曼断裂，参与了二肟 3 通过 S2Cl2 一锅法转化为氰乙基-1,2,3-二噻唑 5 和新型三环戊噻吩 6 的过程；添加硫化锂提高6的收率，由2-(氰乙基)环戊酮肟7生成5和6的收率较高；为这些级联反应提出了反应机制。

  DOI：

  10.1039/b100366f
• 作为产物：
  描述：

  3-(2-氧代环戊基)丙腈 在 sodium hydroxide 、 硫酸羟胺 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以85%的产率得到2-(2-cyanoethyl)cyclopentanone oxime
  参考文献：
  名称：

  Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles

  摘要：

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).

  DOI：

  10.1021/jo00056a021

文献信息

• A novel oxime to pentathiepin cascade reaction
  作者：Sonia Macho、Teresa Rodríguez、Tomás Torroba、Charles W. Rees

  DOI：10.1039/b100366f

  日期：——

  sequence, including a vinylogous sulfur-assisted Beckmann fragmentation, is involved in the one-pot conversion of a dioxime 3 by S2Cl2 into a cyanoethyl-1,2,3-dithiazole 5 and a novel tricyclic pentathiepin 6; the yield of 6 is increased by added lithium sulfide, and both 5 and 6 are formed in higher yield from 2-(cyanoethyl)cyclopentanone oxime 7; reaction mechanisms are proposed for these cascade

  一个广泛的多米诺序列，包括一个乙烯基硫辅助的贝克曼断裂，参与了二肟 3 通过 S2Cl2 一锅法转化为氰乙基-1,2,3-二噻唑 5 和新型三环戊噻吩 6 的过程；添加硫化锂提高6的收率，由2-(氰乙基)环戊酮肟7生成5和6的收率较高；为这些级联反应提出了反应机制。
• From Cyclopentanone Oximes to Bis[1,2,3]dithiazolo-<i>s</i>-indacenes, Cyclopenta[<i>c</i>][1,2]thiazine, Pentathiepino-, Tetrathiino-, and Thienocyclopenta[1,2,3]dithiazoles as a Rich Source of New Materials
  作者：Sonia Macho、Daniel Miguel、Teresa Gómez、Teresa Rodríguez、Tomás Torroba

  DOI：10.1021/jo0514117

  日期：2005.11.1

  The 1,5- and 1,7-s-hydrindacenedione dioximes reacted with S2Cl2 and (Bu3N)-Bu-i to give the first examples of bis[1,2,3]dithiazolo-s-indacenes; one of them was a near-infrared dye. In contrast, the silylated bicyclo[3.3.0]octan-2,6-dione dioxime reacted with S2Cl2 and Et3N to give a bicyclic 4-cyanoethylcyclopenta[1,2,3]dithiazole or, after addition of Li2S, a tricyclic 4-cyanoethyl-5,6-pentathiepinocyclopenta[1,2,3]dithiazole, also obtained from 2-cyanoethylcyclopentanone oxime, S2Cl2, and Hunig's base. In related reactions, 2-oxocyclopentylpropionate oxime gave the expected cyclopenta[1,2,3]dithiazole, in addition to an unexpected cyclopenta[c] [1,2]thiazine that showed a reversible reduction wave in its CV at -0.95 V. Ethyl 2-oxocyclopentanecarboxylate oxime reacted with S2Cl2, Hunig's base, and Li2S to give a 5,6-tetrathiinocyclopenta[1,2,3]dithiazole derivative. Cyclopentathiophen-4-one oximes reacted with S2Cl2 and (Bu3N)-Bu-i to give thienocyclopenta[1,2,3]-dithiazoles that showed UV-vis spectral bands that depended on the positions of the ring fusion.
• Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles
  作者：Robert J. Vijn、Henricus J. Arts、Peter J. Maas、Anna M. Castelijns

  DOI：10.1021/jo00056a021

  日期：1993.2

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).