2(S)-3,3-dimethyl-1-[2-(5-(3-pyridyl)pent-4-enoyl)pyrrolidinyl]pentane-1,2-dione | 457606-37-0

• 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: 2(S)-3,3-dimethyl-1-[2-(5-(3-pyridyl)pent-4-enoyl)pyrrolidinyl]pentane-1,2-dione
• 英文别名: 3,3-dimethyl-1-[(2S)-2-[(E)-5-pyridin-3-ylpent-4-enoyl]pyrrolidin-1-yl]pentane-1,2-dione
• CAS: 457606-37-0
• 化学式: C₂₁H₂₈N₂O₃
• 分子量: 356.465
• InChiKey: TXXOKMNXXWKNMJ-MPNRVQBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  67.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2(S)-3,3-dimethyl-1-[2-(5-(3-pyridyl)pent-4-enoyl)pyrrolidinyl]pentane-1,2-dione 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以87%的产率得到3,3-dimethyl-1-[(2S)-2-(5-(3-pyridyl)pentanoyl)-1-pyrrolidine]-1,2-pentanedione
  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：

  methyl 2(S)-2-oxo-2-(2-pent-4-enoylpyrrolidinyl)acetate 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2(S)-3,3-dimethyl-1-[2-(5-(3-pyridyl)pent-4-enoyl)pyrrolidinyl]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

文献信息

• Synthesis of Ketone Analogues of Prolyl and Pipecolyl Ester FKBP12 Ligands
  作者：Yong-Qian Wu、Douglas E. Wilkinson、David Limburg、Jia-He Li、Hansjorg Sauer、Doug Ross、Shi Liang、Dawn Spicer、Heather Valentine、Mike Fuller、Hong Guo、Pam Howorth、Raj Soni、Yi Chen、Joseph P. Steiner、Gregory S. Hamilton

  DOI：10.1021/jm0200456

  日期：2002.8.1

  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.