(2S,1'R)-4-(5-ethylfuran-2-yl)-2-[(2'-hydroxy-1'-phenylethyl)amino]-4-oxobutanoic acid | 909804-87-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,1'R)-4-(5-ethylfuran-2-yl)-2-[(2'-hydroxy-1'-phenylethyl)amino]-4-oxobutanoic acid
• 英文别名: (2S)-4-(5-ethylfuran-2-yl)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-4-oxobutanoic acid
• CAS: 909804-87-1
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: RTHKYCNRBBNWJA-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,1'R)-4-(5-ethylfuran-2-yl)-2-[(2'-hydroxy-1'-phenylethyl)amino]-4-oxobutanoic acid 在 sodium tetrahydroborate 、 manganese(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以77%的产率得到(2S,4R,1'R)-4-(5-ethylfuran-2-yl)-4-hydroxy-2-[(2'-hydroxy-1'-phenylethyl)amino]-butanoic 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：

  1-(5-乙基-2-呋喃基)乙酮 在 potassium hydrogensulfate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 63.0h， 生成 (2S,1'R)-4-(5-ethylfuran-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

文献信息

• 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.