N-allylcitraconimide | 17423-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-allylcitraconimide
• 英文别名: 1H-Pyrrole-2,5-dione, 3-methyl-1-(2-propenyl)-；3-methyl-1-prop-2-enylpyrrole-2,5-dione
• CAS: 17423-10-8
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: FGERGCLLTZOZLN-UHFFFAOYSA-N

物化性质

• 沸点：
  142-143 °C(Press: 8 Torr)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allylcitraconimide 在 D-葡萄糖-6-磷酸 、 glucose-6-phosphate dehydrogenease 、 Shewanella yellow enzyme 4 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (R)-N-allyl-α-methylsuccinimide
  参考文献：
  名称：

  Asymmetric bioreduction of activated carbon–carbon double bonds using Shewanella yellow enzyme (SYE-4) as novel enoate reductase

  摘要：

  Shewanella yellow enzyme (SYE-4), a novel recombinant enoate reductase, was screened against a variety of different substrates bearing an activated double bond, such as unsaturated cyclic ketones, diesters, and substituted imides. Dimethyl- and ethyl esters of 2-methylmaleic acid were selectively reduced to (R)-configured succinic acid derivatives and various N-substituted maleimides furnished the desired (R)-products in up to >99% enantiomeric excess. Naturally occurring (+)-carvone was selectively reduced to (-)-cis-dihydrocarvone and (-)-carvone was converted to the diastereomeric product, respectively. Overall SYE-4 proved to be a useful biocatalyst for the selective reduction of activated C=C double bonds and complements the pool of synthetic valuable enoate reductases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.092

文献信息

• Regioselective reduction of maleimide and citraconimide derivatives: general preparation of 5-hydroxy-1,5-dihydropyrrol-2-one
  作者：Nobuyuki Mase、Toshiki Nishi、Masaomi Hiyoshi、Kazuhiro Ichihara、Junichiro Bessho、Hidemi Yoda、Kunihiko Takabe

  DOI：10.1039/b200729k

  日期：2002.3.8

  NaBH4 reduction of citraconimide derivatives regioselectively afforded 5-hydroxy-4-methyl-1,5-dihydropyrrol-2-ones, whereas NaBH4–CeCl3 or DIBAL-H reduction gave 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-ones.

  NaBH4对顺丁烯酰胺衍生物的还原选择性地生成了5-羟基-4-甲基-1,5-二氢吡咯-2-酮，而NaBH4–CeCl3或DIBAL-H还原则生成了5-羟基-3-甲基-1,5-二氢吡咯-2-酮。
• Process for the synthesis of citraconimides
  申请人：Akzo Nobel N.V.

  公开号：EP0495544B1

  公开（公告）日：1999-04-07
• PROCESS FOR THE MODIFICATION OF POLYPHENYLENE ETHER RESIN COMPOSITIONS
  申请人：Akzo Nobel N.V.

  公开号：EP0648240A1

  公开（公告）日：1995-04-19
• PROCESS FOR PREPARING A FIBER-REINFORCED COMPOSITE MATERIAL
  申请人：Akzo Nobel Chemicals International B.V.

  公开号：EP2951233B1

  公开（公告）日：2016-12-14
• NATURAL FIBRE-REINFORCED COMPOSITE MATERIAL
  申请人：Green Composites B.V.

  公开号：EP3464428B1

  公开（公告）日：2020-10-14