(2S,4S)-tert-butyl N-tert-butoxycarbonyl-4-difluoromethylpyroglutamate | 527704-92-3

• 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,4S)-tert-butyl N-tert-butoxycarbonyl-4-difluoromethylpyroglutamate
• 英文别名: ditert-butyl (2S,4S)-4-(difluoromethyl)-5-oxopyrrolidine-1,2-dicarboxylate
• CAS: 527704-92-3
• 化学式: C₁₅H₂₃F₂NO₅
• 分子量: 335.348
• InChiKey: CVKBBNJHICIFOI-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4S)-tert-butyl N-tert-butoxycarbonyl-4-difluoromethylpyroglutamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以100%的产率得到(2S,4S)-4-difluoromethylpyroglutamic acid
  参考文献：
  名称：

  Synthesis of cis-4-Trifluoromethyl- and cis-4-Difluoromethyl-l-pyroglutamic Acids

  摘要：

  Efforts to synthesize 4-trifluoromethyl- and 4-difluoromethyl-L-pyroglutamic acids are described. After many arduous efforts, we successfully synthesized our target molecules cis-4-trifluoromethyl-L-pyroglutamic acid 25 and cis-4-difluoromethyl-L-pyroglutamic acid 26 from trams-4-hydroxy-L-proline through oxidation of fluorinated prolinates with RuO4.

  DOI：

  10.1021/jo034098m
• 作为产物：
  描述：

  (4S)-4-(二氟甲基)-1-{[(2-甲基-2-丙基)氧基]羰基}-L-脯氨酸 在 4-二甲氨基吡啶 、 ruthenium(IV) oxide 、 sodium periodate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 (2S,4S)-tert-butyl N-tert-butoxycarbonyl-4-difluoromethylpyroglutamate
  参考文献：
  名称：

  Synthesis of cis-4-Trifluoromethyl- and cis-4-Difluoromethyl-l-pyroglutamic Acids

  摘要：

  Efforts to synthesize 4-trifluoromethyl- and 4-difluoromethyl-L-pyroglutamic acids are described. After many arduous efforts, we successfully synthesized our target molecules cis-4-trifluoromethyl-L-pyroglutamic acid 25 and cis-4-difluoromethyl-L-pyroglutamic acid 26 from trams-4-hydroxy-L-proline through oxidation of fluorinated prolinates with RuO4.

  DOI：

  10.1021/jo034098m

文献信息

• Synthesis of 4-monofluoromethylenyl- and cis-4-monofluoromethyl-l-pyroglutamic acids via a novel dehydrofluorination
  作者：Xiao-Long Qiu、Wei-Dong Meng、Feng-Ling Qing

  DOI：10.1016/j.tet.2004.04.044

  日期：2004.6

  Novel dehydrofluorination reactions accidentally found were used to synthesize terminal monofluoro olefin lactam analogues in good yield. The following hydrogenation of the resulting defluorinated product was systematically investigated. Two important fluorinated amino acids: 4-monofluoromethylenyl-L-pyroglutamic acid 16 and cis-4-monofluoromethyl-L-pyroglutamic acid 17 were synthesized using the methodology. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of <i>cis-</i>4-Trifluoromethyl- and <i>cis</i>-4-Difluoromethyl-<scp>l</scp>-pyroglutamic Acids
  作者：Xiao-Long Qiu、Feng-Ling Qing

  DOI：10.1021/jo034098m

  日期：2003.5.1

  Efforts to synthesize 4-trifluoromethyl- and 4-difluoromethyl-L-pyroglutamic acids are described. After many arduous efforts, we successfully synthesized our target molecules cis-4-trifluoromethyl-L-pyroglutamic acid 25 and cis-4-difluoromethyl-L-pyroglutamic acid 26 from trams-4-hydroxy-L-proline through oxidation of fluorinated prolinates with RuO4.