2-(2-hydroxy-3,3-dimethoxy-propyl)acrylonitrile | 335317-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-hydroxy-3,3-dimethoxy-propyl)acrylonitrile
• 英文别名: 4-Hydroxy-5,5-dimethoxy-2-methylidenepentanenitrile
• CAS: 335317-53-8
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: ILODXHHPHPXVPT-UHFFFAOYSA-N

物化性质

• 沸点：
  298.6±40.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxy-3,3-dimethoxy-propyl)acrylonitrile 在 ion-exchange resin Ag-50 W-X₈ 、 sodium methylate 、 氢气 、 磷脂酶B 作用下， 以 甲醇 、 水 为溶剂， 反应 53.0h， 生成 (R)-(+)-4-hydroxy-2-methylidene-5-oxo-pentanenitrile
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral substituted acrylate and acrylonitrile precursors for the synthesis of 3-deoxy-2-ulosonic acids and α-methylene-γ-lactones

  摘要：

  Substituted acrylonitrile and ethyl acrylate bearing a masked alpha -hydroxyaldehyde were easily synthesised by a Barbier type reaction between the monoacetal of glyoxal and bromomethyl acrylonitrile or ethyl bromomethyl acrylate. We prepared these interesting synthons in an enantiomerically pure form by enzymatic resolution with Candida rugosa lipase. or by microbial reduction of the corresponding ketones using Aspergillus niger and Lactobacillus kefir. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00155-0
• 作为产物：
  描述：

  2-(bromomethyl)acrylonitrile 、 乙二醛-1,1-二甲基乙缩醛溶液 在 indium 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 7.0h， 以96%的产率得到2-(2-hydroxy-3,3-dimethoxy-propyl)acrylonitrile
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral substituted acrylate and acrylonitrile precursors for the synthesis of 3-deoxy-2-ulosonic acids and α-methylene-γ-lactones

  摘要：

  Substituted acrylonitrile and ethyl acrylate bearing a masked alpha -hydroxyaldehyde were easily synthesised by a Barbier type reaction between the monoacetal of glyoxal and bromomethyl acrylonitrile or ethyl bromomethyl acrylate. We prepared these interesting synthons in an enantiomerically pure form by enzymatic resolution with Candida rugosa lipase. or by microbial reduction of the corresponding ketones using Aspergillus niger and Lactobacillus kefir. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00155-0

文献信息

• Chemoenzymatic synthesis of chiral substituted acrylate and acrylonitrile precursors for the synthesis of 3-deoxy-2-ulosonic acids and α-methylene-γ-lactones
  作者：D. Crestia、C. Guérard、H. Veschambre、L. Hecquet、C. Demuynck、J. Bolte

  DOI：10.1016/s0957-4166(01)00155-0

  日期：2001.4

  Substituted acrylonitrile and ethyl acrylate bearing a masked alpha -hydroxyaldehyde were easily synthesised by a Barbier type reaction between the monoacetal of glyoxal and bromomethyl acrylonitrile or ethyl bromomethyl acrylate. We prepared these interesting synthons in an enantiomerically pure form by enzymatic resolution with Candida rugosa lipase. or by microbial reduction of the corresponding ketones using Aspergillus niger and Lactobacillus kefir. (C) 2001 Elsevier Science Ltd. All rights reserved.