(3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid | 252681-04-2

• 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: (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid
• 英文别名: 2,2-difluoro-3-(2-hydroxy-1R-phenylethylamino)-3S-phenylpropionic acid；(3S)-2,2-difluoro-3-[[(1R)-2-hydroxy-1-phenylethyl]amino]-3-phenylpropanoic acid
• CAS: 252681-04-2
• 化学式: C₁₇H₁₇F₂NO₃
• 分子量: 321.324
• InChiKey: AJSWJHQBOPNUTI-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-{((S)-3-Amino-2,2-difluoro-3-phenyl-propionyl)-[(ethoxycarbonylmethyl-carbamoyl)-phenyl-methyl]-amino}-malonic acid monobenzyl ester
  参考文献：
  名称：

  Synthesis of difluorinated pseudopeptides using chiral α,α-difluoro-β-amino acids in the Ugi reaction

  摘要：

  2,2-Difluoro-3-(2-hydroxy-1 R-phenylethylamino)-3 S-phenylpropionic acid 3, obtained by a Reformatsky-type reaction of ethyl bromodifluoroacetate with (4R)-2,4-diphenyloxazolidine, was used as a classical carboxylic acid in the Ugi reaction to prepare various difluorinated pseudopeptides 5a-n. Compounds 5 were then deprotected by hydrogenolysis to furnish difluorinated pseudopeptides 6. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.019
• 作为产物：
  描述：

  2,4-diphenyl-1,3-oxazolidine 在 盐酸 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of α,α-Difluoro-β-amino Acid and 3,3-Difluoroazetidin-2-one via the Reformatsky-Type Reaction of Ethyl Bromodifluoroacetate with Chiral 1,3-Oxazolidines

  摘要：

  Chiral oxazolidines 2a-e can be diastereoselectively alkylated with BrCF2CO2Et to furnish 3,3-difluoroazetidin-2-ones 3a-e with up to 99% de. Selective cleavage of the chiral appendage provided the corresponding unsubstituted azetidinones. Formation of optically pure a,a-difluoro-P-amino acids 5a-c can be achieved by acidic hydrolysis of N-vinyl-azetidin-2-ones.

  DOI：

  10.1021/jo990868b

文献信息

• Enantioselective Synthesis of α,α-Difluoro-β-amino Acid and 3,3-Difluoroazetidin-2-one via the Reformatsky-Type Reaction of Ethyl Bromodifluoroacetate with Chiral 1,3-Oxazolidines
  作者：Stéphane Marcotte、Xavier Pannecoucke、Christian Feasson、Jean-Charles Quirion

  DOI：10.1021/jo990868b

  日期：1999.11.1

  Chiral oxazolidines 2a-e can be diastereoselectively alkylated with BrCF2CO2Et to furnish 3,3-difluoroazetidin-2-ones 3a-e with up to 99% de. Selective cleavage of the chiral appendage provided the corresponding unsubstituted azetidinones. Formation of optically pure a,a-difluoro-P-amino acids 5a-c can be achieved by acidic hydrolysis of N-vinyl-azetidin-2-ones.
• Synthesis of difluorinated pseudopeptides using chiral α,α-difluoro-β-amino acids in the Ugi reaction
  作者：Vanessa Gouge、Philippe Jubault、Jean-Charles Quirion

  DOI：10.1016/j.tetlet.2003.11.019

  日期：2004.1

  2,2-Difluoro-3-(2-hydroxy-1 R-phenylethylamino)-3 S-phenylpropionic acid 3, obtained by a Reformatsky-type reaction of ethyl bromodifluoroacetate with (4R)-2,4-diphenyloxazolidine, was used as a classical carboxylic acid in the Ugi reaction to prepare various difluorinated pseudopeptides 5a-n. Compounds 5 were then deprotected by hydrogenolysis to furnish difluorinated pseudopeptides 6. (C) 2003 Elsevier Ltd. All rights reserved.