(S)-(-)-4-hydroxy-2-methylidene-5-oxo-pentanenitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(-)-4-hydroxy-2-methylidene-5-oxo-pentanenitrile
• 英文别名: (4S)-4-hydroxy-2-methylidene-5-oxopentanenitrile
• 化学式: C₆H₇NO₂
• 分子量: 125.127
• InChiKey: QBOFUTOZHVTRCU-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-4-hydroxy-2-methylidene-5-oxo-pentanenitrile 在 rabbit muscle aldolase 、 盐酸 、 sodium hydroxide 、 acid phytase from Aspergillus ficuum 作用下， 反应 70.0h， 生成 (-)-6-deoxy-6-(1'-cyanovinyl)-β-L-sorbofuranose
  参考文献：
  名称：

  Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

  摘要：

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.069
• 作为产物：
  描述：

  2-(2-hydroxy-3,3-dimethoxy-propyl)acrylonitrile 在 4 A molecular sieve 、 Aspergillus niger 、 ion-exchange resin Ag-50 W-X₈ 、 氢气 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 101.0h， 生成 (S)-(-)-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

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.
• Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues
  作者：Dominique Crestia、Colette Demuynck、Jean Bolte

  DOI：10.1016/j.tet.2003.12.069

  日期：2004.3

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.