(2S)-1,1-diethoxybut-3-en-2-ol | 1462896-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-1,1-diethoxybut-3-en-2-ol
• CAS: 1462896-59-8
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: DSZHIRKLQRADHJ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯醛缩二乙醇 在 正丁基锂 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 乙腈 、 正戊烷 为溶剂， 反应 71.0h， 生成 [(2R)-1,1-diethoxybut-3-en-2-yl] acetate 、 (2S)-1,1-diethoxybut-3-en-2-ol
  参考文献：
  名称：

  Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses

  摘要：

  Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.016

文献信息

• Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses
  作者：Flora Camps Bres、Christine Guérard-Hélaine、Carlos Fernandes、José A. Castillo、Marielle Lemaire

  DOI：10.1016/j.tetasy.2013.07.016

  日期：2013.9

  Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA. (C) 2013 Elsevier Ltd. All rights reserved.