DL-2-hydroxybutanal diethyl acetal | 107646-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: DL-2-hydroxybutanal diethyl acetal
• 英文别名: 1,1-diethoxy 2-butanol；1,1-Diethoxybutan-2-ol
• CAS: 107646-10-6
• 化学式: C₈H₁₈O₃
• 分子量: 162.229
• InChiKey: PKCRNWHXRHTSLZ-UHFFFAOYSA-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

• 作为反应物：
  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
• 作为产物：
  描述：

  1,1-Diethoxy-2-acetoxy-ethan 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.25h， 生成 DL-2-hydroxybutanal diethyl acetal
  参考文献：
  名称：

  Bernard, Didier; Doutheau, Alain; Gore, Jacques, Synthetic Communications, 1987, vol. 17, # 15, p. 1807 - 1814

  摘要：

  DOI：

文献信息

• Dissymetrisation de la molecule de glyoxal
  作者：A. Stambouli、R. Amouroux、F. Chastrette、M. Chastrette、G. Mattioda、A. Blanc

  DOI：10.1016/0022-328x(86)80467-3

  日期：1986.6

  Various organometallic compounds are treated with 1-acetoxy-1,2,2-triethoxyethane (1) an asymmetric derivative of glyoxal. Two kinds of reactions are observed depending on the nature of the organometallic reagents. Organolithium compounds give exclusively addition to the ester carbonyl group, while organocuprate derivatives lead to substitution of the acetoxy group. With Grignard reagents both reactions

  各种有机金属化合物用乙二醛的不对称衍生物1-乙酰氧基-1,2,2-三乙氧基乙烷（1）处理。根据有机金属试剂的性质，观察到两种反应。有机锂化合物仅加成酯羰基，而有机铜酸酯衍生物导致乙酰氧基的取代。使用格氏试剂，都会发生两个反应，加成和取代产物的比例取决于溶剂和烷基。讨论了路易斯酸的作用。
• Preparation of optically pure L-2-hydroxyaldehydes with yeast transketolase
  作者：Franz Effenberger、Volker Null、Thomas Ziegler

  DOI：10.1016/s0040-4039(00)79121-0

  日期：1992.9

  L-2-Hydroxyaldehydes L-3 with a great variety of substituents in 3-position are obtained in good chemical and excellent optical yields by kinetic resolution in the transketolase-catalyzed reaction of racemic 2-hydroxyaldehydes with lithium hydroxypyruvate 4 where only the enantiomer (R)-3 reacts to 5-deoxy-D-xyluloses 5.

  L-2-羟基醛L- 3在3位上有很大的各种取代基以良好的化学和由外消旋2-羟基醛的转酮酶-催化反应动力学拆分良好的光学收率与锂羟基丙酮酸得到4，其中只对映异构体（R）-3与5-脱氧-D-木酮糖5反应。
• Water-Soluble Polymer Alkanals
  申请人：Kozlowski Antoni

  公开号：US20110034737A1

  公开（公告）日：2011-02-10

  The present invention is directed to alkanal derivatives of water-soluble polymers such as poly(ethylene glycol), their corresponding hydrates and acetals, and to methods for preparing and using such polymer alkanals. The polymer alkanals of the invention are prepared in high purity and exhibit storage stability.

  本发明涉及水溶性聚合物（例如聚乙二醇）的醛基衍生物，其对应的水合物和缩醛，以及制备和使用这种聚合物醛的方法。本发明的聚合物醛在高纯度下制备，并具有储存稳定性。
• The efficient resolution of protected diols and hydroxy aldehydes by lipases: steric auxiliary approach and synthetic applications
  作者：Mahn-Joo Kim、In Taek Lim、Gil-Bae Choi、Sang-Yeul Whang、Bon-Cheol Ku、Jin-Young Choi

  DOI：10.1016/0960-894x(95)00550-d

  日期：1996.1

  1,n-Diols (n = 2 - 5) and 2-hydroxy aldehydes protected with a steric auxiliary are transformed by Pseudomonas lipases with high enantioselectivity, thus allowing the efficient resolution of these molecules and the synthesis of related derivatives with high optical purity.
• STAMBOULI, A.;AMOUROUX, R.;CHASTRETTE, F.;CHASTRETTE, M.;MATTIODA, G.;BLA+, J. ORGANOMET. CHEM., 1986, 307, N 2, 139-144
  作者：STAMBOULI, A.、AMOUROUX, R.、CHASTRETTE, F.、CHASTRETTE, M.、MATTIODA, G.、BLA+

  DOI：——

  日期：——