(S)-tert-butyl 2-pentanoylpyrrolidine-1-carboxylate | 1026513-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-tert-butyl 2-pentanoylpyrrolidine-1-carboxylate
• 英文别名: Tert-butyl (2S)-2-pentanoylpyrrolidine-1-carboxylate
• CAS: 1026513-04-1
• 化学式: C₁₄H₂₅NO₃
• 分子量: 255.357
• InChiKey: HNFSYXJPKZSUKG-NSHDSACASA-N

物化性质

• 沸点：
  342.5±35.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-pentanoylpyrrolidine-1-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,3-Dimethyl-1-((S)-2-pentanoyl-pyrrolidin-1-yl)-pentane-1,2-dione
  参考文献：
  名称：

  Synthesis of Ketone Analogues of Prolyl and Pipecolyl Ester FKBP12 Ligands

  摘要：

  The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.

  DOI：

  10.1021/jm0200456
• 作为产物：
  描述：

  N-(叔丁氧基羰基)-L-脯氨酸-N′-甲氧基-N′-甲酰胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 生成 (S)-tert-butyl 2-pentanoylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Ketone Analogues of Prolyl and Pipecolyl Ester FKBP12 Ligands

  摘要：

  The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.

  DOI：

  10.1021/jm0200456

文献信息

• Asymmetric Synthesis of (α<i>R</i>)-Polyfluoroalkylated Prolinols Based on the Perfluoroalkyl-Induced Highly Stereoselective Reduction of Perfluoroalkyl <i>N</i>-Boc-pyrrolidyl Ketones
  作者：Kazumasa Funabiki、Akitsugu Shibata、Hiroki Iwata、Keisuke Hatano、Yasuhiro Kubota、Kenichi Komura、Masahiro Ebihara、Masaki Matsui

  DOI：10.1021/jo8004952

  日期：2008.6.1

  Reduction of the obtained chiral (S)-tert-butyl 2-(perfluoroalkanoyl)pyrrolidine-1-carboxylate with sodium borohydride or lithium aluminum hydride proceeded smoothly to give the corresponding (S)-tert-butyl 2-((R)-perfluoro-1-hydroxyalkyl)pyrrolidine-1-carboxylate in yields of 73−97% with excellent diastereoselectivities (up to >98% de), compared with the reduction of nonfluorinated (S)-tert-butyl

  用硼氢化钠或氢化锂铝将所得的手性（S）-叔丁基2-（全氟烷酰基）吡咯烷-1-羧酸还原反应顺利进行，得到相应的（S）-叔丁基2-（（R）-全氟化合物-1-羟基烷基）吡咯烷-1-羧酸盐的收率为73-97％，非对映选择性极好（高达> 98％de），与未氟化的（S）-叔丁基-2-戊酰基吡咯烷-1-羧酸盐的减少相比。