(+/-)-ethyl 2-cyano-2-hydroxyacetate | 137622-41-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-ethyl 2-cyano-2-hydroxyacetate
• 英文别名: ethyl 2-cyano-2-hydroxyacetate
• CAS: 137622-41-4
• 化学式: C₅H₇NO₃
• 分子量: 129.115
• InChiKey: IYPJQABCLBFGTB-UHFFFAOYSA-N

物化性质

• 沸点：
  266.0±20.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-ethyl 2-cyano-2-hydroxyacetate 在 盐酸 、 硼烷四氢呋喃络合物 、 nickel dichloride 作用下， 生成 DL-异丝氨酸
  参考文献：
  名称：

  A simple total synthesis of (S)-isoserine

  摘要：

  Kinetic enzymatic resolution by Candida cylindracea lipase of racemic isoserine diacetate prepared from the cyanohydrin of glyoxylate provided (S)-isoserine in good yeild and high optical purity.

  DOI：

  10.1016/s0957-4166(00)82197-7
• 作为产物：
  描述：

  乙醛酸乙酯 、 三甲基氰硅烷 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 18.25h， 生成 (+/-)-ethyl 2-cyano-2-hydroxyacetate
  参考文献：
  名称：

  Redox-Neutral α-Cyanation of Amines

  摘要：

  alpha-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine alpha-cyanation/N-alkylation or alternatively, alpha-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.

  DOI：

  10.1021/ja308009g

文献信息

• A simple total synthesis of naturally occurring hydroxy-amino acids by enzymatic kinetic resolution
  作者：Yang Lu、Christine Miet、Nicole Kunesch、Jacques E. Poisson

  DOI：10.1016/s0957-4166(00)80128-7

  日期：1993.5

  Both optically pure enantiomers of GABOB and isoserine were obtained by enzymatic kinetic resolution of acetylated precursors in three or four steps. The key intermediates were cyanohydrins available from simple aldehydes. This procedure can be applied to other unusual hydroxy amino acids widely distributed in biologically important peptides.
• Kunesch, Nicole; Miet, Christine; Poisson, Jacques, Liebigs Annalen der Chemie, 1994, # 11, p. 1059 - 1064
  作者：Kunesch, Nicole、Miet, Christine、Poisson, Jacques

  DOI：——

  日期：——
• Redox-Neutral α-Cyanation of Amines
  作者：Longle Ma、Weijie Chen、Daniel Seidel

  DOI：10.1021/ja308009g

  日期：2012.9.19

  alpha-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine alpha-cyanation/N-alkylation or alternatively, alpha-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.
• A simple total synthesis of (S)-isoserine
  作者：Yang Lu、Christine Miet、Nicole Kunesch、Jacques E. Poisson

  DOI：10.1016/s0957-4166(00)82197-7

  日期：1991.1

  Kinetic enzymatic resolution by Candida cylindracea lipase of racemic isoserine diacetate prepared from the cyanohydrin of glyoxylate provided (S)-isoserine in good yeild and high optical purity.