(2S,4R,1'S)-4-(furan-2-yl)-4-hydroxy-2-[(1'-phenylethyl)amino]-butanoic acid | 909804-91-7

• 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,4R,1'S)-4-(furan-2-yl)-4-hydroxy-2-[(1'-phenylethyl)amino]-butanoic acid
• 英文别名: (2S,4R)-4-(furan-2-yl)-4-hydroxy-2-[[(1S)-1-phenylethyl]amino]butanoic acid
• CAS: 909804-91-7
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: ZKNTXWYJENQQRV-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R,1'S)-4-(furan-2-yl)-4-hydroxy-2-[(1'-phenylethyl)amino]-butanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以51%的产率得到(2R,4S,1''S)-4-[(1''-phenylethyl)amino]-3,4-dihydro-2,2'-bifuran-5(2H)-one
  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：

  4-(2-furyl)-2-hydroxy-4-oxobutanoic acid 在 sodium tetrahydroborate 、 potassium hydrogensulfate 、 manganese(ll) chloride 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 27.0h， 生成 (2S,4R,1'S)-4-(furan-2-yl)-4-hydroxy-2-[(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

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.