2-(5-oxotetrahydrofuran-2-yl)acetonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-(5-oxotetrahydrofuran-2-yl)acetonitrile
• 英文别名: 2-(5-Oxooxolan-2-yl)acetonitrile
• 化学式: C₆H₇NO₂
• 分子量: 125.127
• InChiKey: PKEXJRGFRXIJRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(四氢呋喃-2-基)乙腈 在 iron(II) triflate 、 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine 、 氧气 作用下， 60.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以3%的产率得到2-(5-oxotetrahydrofuran-2-yl)acetonitrile
  参考文献：
  名称：

  Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst

  摘要：

  Selective alpha-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective alpha-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O-2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H-2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O-2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H-2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.

  DOI：

  10.1021/ja502167h

文献信息

• Polyimide comprising sulfonic acid group at the terminal of side chain, and polymer electrolyte and fuel cell using the same
  申请人：Jung Myung-sup

  公开号：US20050181257A1

  公开（公告）日：2005-08-18

  The present invention is related to a polyimide, which has high ionic conductivity and good structural stability, does not decompose even under low humidity, and is inexpensive, and a polymer electrolyte and a fuel cell using the same. In particular, the polyimide of the present invention has a repeating unit of Formula (1) below and also includes a reactive blocking group derived from a monoamine compound or monoanhydride compound having at least one carbon-carbon double bond at a terminal or at both terminals:

  本发明涉及一种聚酰亚胺，它具有高离子导电性和良好的结构稳定性，即使在低湿度条件下也不会分解，而且价格低廉，还涉及使用这种聚酰亚胺的聚合物电解质和燃料电池。特别是，本发明的聚酰亚胺具有下式（1）的重复单元，还包括一个反应性封端基团，该基团来源于在一个末端或两个末端具有至少一个碳碳双键的单胺化合物或单酐化合物：
• A Direct Method for the Conversion of Terminal Epoxides into γ-Butanolides
  作者：Mohammad Movassaghi、Eric N. Jacobsen

  DOI：10.1021/ja025604c

  日期：2002.3.1

  A new and efficient process for the conversion of terminal epoxides to gamma-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine and boron trifluoride diethyl etherate in dichloromethane at 0 degrees C rapidly affords a cyclic keteneaminal that can be hydrolyzed and protodesilylated under mild conditions to provide the corresponding gamma-butanolide in high yield. The net transformation is equivalent to an acetate enolate opening of terminal epoxides. The formation of a cyclic keteneaminal as the direct addition product was observed by monitoring of the reaction by IR and NMR spectroscopy. Functionalized gamma-lactones were prepared by the interception of the reactive cyclic keteneaminal prior to hydrolysis. Reactions with enantiomerically enriched terminal epoxides provide the corresponding gamma-butanolides without loss of optical activity. The compatibility of the present methodology with a wide range of functional groups is noteworthy.
• ION CONDUCTORS
  申请人：SECRETARY OF STATE FOR DEFENCE IN HER BRITANNIC MAJESTY'S GOV. OF THE UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND

  公开号：EP0380490B1

  公开（公告）日：1992-09-16
• PESTICIDAL FORMULATIONS
  申请人：Syngenta Limited

  公开号：EP1441587A1

  公开（公告）日：2004-08-04
• US5538618A
  申请人：——

  公开号：US5538618A

  公开（公告）日：1996-07-23