3,3-二乙氧基丙酰肼 | 6191-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,3-二乙氧基丙酰肼
• 英文名称: (R)-Atrolactinsaeureamid
• 英文别名: Atrolactamide；(R)-atrolactinic acid amide；(R)-2-Hydroxy-2-phenyl-propionsaeure-amid；(R)-Atrolactinsaeure-amid；((-)-Atrolactinsaeure)-amid；Atrolactamide, (R)-；(2R)-2-hydroxy-2-phenylpropanamide
• CAS: 6191-36-2
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: FWTXWYXPXGKVJG-SECBINFHSA-N

物化性质

• 沸点：
  349.3±35.0 °C(Predicted)
• 密度：
  1.197±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-二乙氧基丙酰肼 、 丙酮 生成 (5R)-5-Methyl-5-phenyl-1,3-oxazolidin-4-one
  参考文献：
  名称：

  Schrader, Thomas, Angewandte Chemie, 1995, vol. 107, # 8, p. 1001 - 1002

  摘要：

  DOI：
• 作为产物：
  描述：

  扁桃腈 在 三异丙氧基氯化钛 、 盐酸 、 N,N-二甲基丙烯基脲 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 3,3-二乙氧基丙酰肼
  参考文献：
  名称：

  Stereoselective Umpolung Reactions with MetalatedP-Chiral Cyanohydrin Phosphates—Enantioselective Synthesis of Tertiary Cyanohydrins

  摘要：

  AbstractWe present the first cyanohydrin derivative4that allows diastereoselective umpolung reactions. In4the OH group of the cyanohydrin is linked with a chiral phosphate, which can be removed hydrolytically after asymmetric synthesis. Cyclization of pseudoephedrine1dwith POCl3gave2d. This was followed by addition of racemic benzaldehyde cyanohydrin3to give the key intermediate4dwith complete retention of the configuration at phosphorus. Deprotonation of4d, followed by addition of a wide variety of electrophiles afforded the crystalline products5with high diastereomeric excesses (deup to 94%). High asymmetric induction was also achieved for the reaction of4−Li+with acyl halides, α‐bromoacetates, 2‐cycloalkenones, α,β‐unsaturated esters, and γ‐bromoacetates. Lewis acid assisted hydrolysis proceeded without racemization and gave high yields of ketone cyanohydrins6. From the ring‐opened chiral auxiliary7, optically pure pseudoephedrine1was readily recovered by acid hydrolysis. Optically pure (R) and (S) ketone cyanohydrins are now accessible in a very general strategy, which circumvents the substrate limitations of enzymatic synthesis.

  DOI：

  10.1002/chem.19970030815

文献信息

• Freudenberg; Todd; Seidler, Justus Liebigs Annalen der Chemie, 1933, vol. 501, p. 208
  作者：Freudenberg、Todd、Seidler

  DOI：——

  日期：——
• Reactions of chiral β-ketosulfoxides with Et2AlCN: Asymmetric synthesis of cyanohydrin derivatives.
  作者：J.L. García Ruano、A.M. Martín Castro、J.H. Rodriguez

  DOI：10.1016/s0040-4039(00)79720-6

  日期：1991.7
• Extent and Severity of Groundwater Arsenic Contamination in Bangladesh
  作者：Md. Abul Fazal、Toshihiko Kawachi、Eiji Ichion

  DOI：10.1080/02508060108686929

  日期：2001.9
• McKenzie; Smith, Journal of the Chemical Society, 1922, vol. 121, p. 1361
  作者：McKenzie、Smith

  DOI：——

  日期：——
• Stereoselective Umpolung Reactions with MetalatedP-Chiral Cyanohydrin Phosphates—Enantioselective Synthesis of Tertiary Cyanohydrins
  作者：Thomas Schrader

  DOI：10.1002/chem.19970030815

  日期：1997.8

  AbstractWe present the first cyanohydrin derivative4that allows diastereoselective umpolung reactions. In4the OH group of the cyanohydrin is linked with a chiral phosphate, which can be removed hydrolytically after asymmetric synthesis. Cyclization of pseudoephedrine1dwith POCl3gave2d. This was followed by addition of racemic benzaldehyde cyanohydrin3to give the key intermediate4dwith complete retention of the configuration at phosphorus. Deprotonation of4d, followed by addition of a wide variety of electrophiles afforded the crystalline products5with high diastereomeric excesses (deup to 94%). High asymmetric induction was also achieved for the reaction of4−Li+with acyl halides, α‐bromoacetates, 2‐cycloalkenones, α,β‐unsaturated esters, and γ‐bromoacetates. Lewis acid assisted hydrolysis proceeded without racemization and gave high yields of ketone cyanohydrins6. From the ring‐opened chiral auxiliary7, optically pure pseudoephedrine1was readily recovered by acid hydrolysis. Optically pure (R) and (S) ketone cyanohydrins are now accessible in a very general strategy, which circumvents the substrate limitations of enzymatic synthesis.