D-(+)-2-hydroxybutanal diethyl acetal | 137873-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-(+)-2-hydroxybutanal diethyl acetal
• 英文别名: (2R)-1,1-diethoxybutan-2-ol
• CAS: 137873-17-7
• 化学式: C₈H₁₈O₃
• 分子量: 162.229
• InChiKey: PKCRNWHXRHTSLZ-SSDOTTSWSA-N

物化性质

• 沸点：
  223.5±20.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  DL-2-hydroxybutanal diethyl acetal 生成 D-(+)-2-hydroxybutanal diethyl acetal
  参考文献：
  名称：

  Deoxyribose 5-phosphate aldolase as a catalyst in asymmetric aldol condensation

  摘要：

  This paper describes the substrate specificity and synthetic utility of deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4). Eight donors and 20 acceptors have been tested as substrates. In addition to acetaldehyde, propanal, acetone, and fluoroacetone have been used to condense with a number of acceptor aldehydes. Thirteen aldol products have been prepared and characterized. A new stereogenic center with 3(S) configuration is formed when acetaldehyde, fluoroacetone, or acetone is used as a donor substrate. With propanal, two new stereogenic centers are formed with 2(R) and 3(S) configurations. The acceptor substrates have very little structural requirements. The 2-hydroxyaldehydes appear to react the fastest, and the D-isomers are better substrates than the L-isomers. The stereospecificity is absolute regardless of the chirality of 2-hydroxyaldehydes. The aldol reactions thus follow the Cram-Felkin mode of attack for D-substrates and anti-Cram-Felkin mode of attack for L-substrates.

  DOI：

  10.1021/ja00028a050

文献信息

• Deoxyribose 5-phosphate aldolase as a catalyst in asymmetric aldol condensation
  作者：Lihren Chen、David P. Dumas、Chi Huey Wong

  DOI：10.1021/ja00028a050

  日期：1992.1

  This paper describes the substrate specificity and synthetic utility of deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4). Eight donors and 20 acceptors have been tested as substrates. In addition to acetaldehyde, propanal, acetone, and fluoroacetone have been used to condense with a number of acceptor aldehydes. Thirteen aldol products have been prepared and characterized. A new stereogenic center with 3(S) configuration is formed when acetaldehyde, fluoroacetone, or acetone is used as a donor substrate. With propanal, two new stereogenic centers are formed with 2(R) and 3(S) configurations. The acceptor substrates have very little structural requirements. The 2-hydroxyaldehydes appear to react the fastest, and the D-isomers are better substrates than the L-isomers. The stereospecificity is absolute regardless of the chirality of 2-hydroxyaldehydes. The aldol reactions thus follow the Cram-Felkin mode of attack for D-substrates and anti-Cram-Felkin mode of attack for L-substrates.