(E)-ethyl 2-(2-furyl)-2-(hydroxyimino)acetate | 201871-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-ethyl 2-(2-furyl)-2-(hydroxyimino)acetate
• 英文别名: ethyl (2E)-2-(furan-2-yl)-2-hydroxyiminoacetate
• CAS: 201871-35-4
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: MCFMJXRUAVTLGJ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(2-furyl)-2-(hydroxyimino)acetate 在 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (S)-2-amino-2-(furan-2-yl)ethanol
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars

  摘要：

  The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00158-7
• 作为产物：
  描述：

  α-氧代-2-呋喃乙酸 在 盐酸 、 硫酸 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醚 、 乙醇 、 氯仿 为溶剂， 反应 22.0h， 生成 (E)-ethyl 2-(2-furyl)-2-(hydroxyimino)acetate
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars

  摘要：

  The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00158-7

文献信息

• Ethyl (<i>E</i>)-2-Furyl-2-(hydroxyimino)acetate
  作者：D. Ülkü、M. N. Tahir、A. S. Demir、H. Aksoy-Çam

  DOI：10.1107/s0108270197009852

  日期：1998.1.15

  In the title compound, C8H9NO4, the hydrogen bonds between the oxime O atoms and the N and O atoms of the neighbouring asymmetric unit result in the dimerization of the molecules, with D...A distances of 2.774 (3) and 3.144 (3) Angstrom for O-H ... N and O-H ... O, respectively. The hydrogen-bridged centrosymmetric dimers are cross-linked via additional weaker intermolecular hydrogen bonds between the CH3 group and the other O atom of the dimer, forming a polymeric network. The D...A distance of this second-order interaction (C-H ... O) is 3.450 (2) Angstrom. Structure analysis indicates that the oxime is in an E configuration. The whole molecule is planar, with a maximum deviation from the least-squares plane of 0.104 (2) Angstrom.
• Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars
  作者：Ayhan S. Demir、Özge Sesenoglu、Hilal Aksoy-Cam、Handan Kaya、Kenan Aydogan

  DOI：10.1016/s0957-4166(03)00158-7

  日期：2003.5

  The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%. (C) 2003 Elsevier Science Ltd. All rights reserved.