4-(2-furyl)-2-hydroxy-4-oxobutanoic acid | 93579-54-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 4-(2-furyl)-2-hydroxy-4-oxobutanoic acid
• 英文别名: 4-(Furan-2-yl)-2-hydroxy-4-oxobutanoic acid
• CAS: 93579-54-5
• 化学式: C₈H₈O₅
• 分子量: 184.149
• InChiKey: XTAFOQLPSCHBTE-UHFFFAOYSA-N

物化性质

• 沸点：
  448.4±40.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 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：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-furyl)-2-hydroxy-4-oxobutanoic acid 在 potassium hydrogensulfate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 26.5h， 生成 (2S,1'R)-4-(furan-2-yl)-2-[(2'-hydroxy-1'-phenylethyl)amino]-4-oxobutanoic acid
  参考文献：
  名称：

  Crystallisation induced asymmetric transformation (CIAT) in the synthesis of furoylalanines and furylcarbinols

  摘要：

  A new synthesis of enantiomerically highly enriched N-substituted furoylalanines has been developed. This process involves the combination of crystallisation induced asymmetric transformation (CIAT) and a conjugate addition of N-nucleophiles to furoylacrylic acids. Further transformations to furoylalanines and substituted furylcarbinols are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.024
• 作为产物：
  描述：

  2-乙酰基呋喃 、 乙醛酸 以 水 为溶剂， 反应 12.0h， 生成 4-(2-furyl)-2-hydroxy-4-oxobutanoic acid
  参考文献：
  名称：

  Crystallisation induced asymmetric transformation (CIAT) in the synthesis of furoylalanines and furylcarbinols

  摘要：

  A new synthesis of enantiomerically highly enriched N-substituted furoylalanines has been developed. This process involves the combination of crystallisation induced asymmetric transformation (CIAT) and a conjugate addition of N-nucleophiles to furoylacrylic acids. Further transformations to furoylalanines and substituted furylcarbinols are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.024

文献信息

• Clay montmorillonite K10 catalyzed aldol-type reaction of aldehydes with silyl enol ethers in water
  作者：Teck-Peng Loh、Xu-Ran Li

  DOI：10.1016/s0040-4020(99)00594-3

  日期：1999.8

  for the cross aldol reaction of silyl enol ethers and ketene silyl acetal with various aldehydes using montmorillonite K10 is described. Cheap and commercially available montmorillonite K10 can be used without the need of an ion exchange process under solvent-free conditions or in water. Hydrate of aldehydes such as glyoxylic acid can be used directly. Thermal treatment of K10 increased the catalytic

  描述了一种环境友好的方法，该方法使用蒙脱石K10使甲硅烷基烯醇醚和乙烯酮甲硅烷基乙缩醛与各种醛发生交叉醇醛缩合反应。在无溶剂条件下或在水中无需离子交换过程即可使用廉价的市售蒙脱土K10。醛的水合物，例如乙醛酸可直接使用。K10的热处理提高了催化活性。推测其催化活性是由于K10的结构特性及其固有的布朗斯台德酸度。
• Direct Aldol Reactions of Glycoxylic Acid Monohydrate with Ketones
  作者：Teck-Peng Loh、Lin-Li Wei、Li-Chun Feng

  DOI：10.1055/s-1999-2786

  日期：1999.7
• Crystallisation induced asymmetric transformation (CIAT) in the synthesis of furoylalanines and furylcarbinols
  作者：Pavol Jakubec、Dušan Berkeš、Richard Šiška、Mária Gardianová、František Považanec

  DOI：10.1016/j.tetasy.2006.04.024

  日期：2006.7

  A new synthesis of enantiomerically highly enriched N-substituted furoylalanines has been developed. This process involves the combination of crystallisation induced asymmetric transformation (CIAT) and a conjugate addition of N-nucleophiles to furoylacrylic acids. Further transformations to furoylalanines and substituted furylcarbinols are also described. (c) 2006 Elsevier Ltd. All rights reserved.