N-(butyloxycarbonyl)-2(S)-(1-oxo-4-pentenyl)pyrrolidine | 106493-65-6

• 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: N-(butyloxycarbonyl)-2(S)-(1-oxo-4-pentenyl)pyrrolidine
• 英文别名: tert-butyl 2(S)-2-pent-4-enoylpyrrolidinecarboxylate；(S)-tert-butyl 2-(pent-4-enoyl)pyrrolidine-1-carboxylate；tert-butyl (2S)-2-(pent-4-enoyl)pyrrolidine-1-carboxylate；tert-butyl (2S)-2-pent-4-enoylpyrrolidine-1-carboxylate
• CAS: 106493-65-6
• 化学式: C₁₄H₂₃NO₃
• 分子量: 253.342
• InChiKey: CBLPADASFDBTOJ-NSHDSACASA-N

物化性质

• 沸点：
  347.1±35.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  N-(butyloxycarbonyl)-2(S)-(1-oxo-4-pentenyl)pyrrolidine 在 苄基三甲基氢氧化铵 、 臭氧 、 magnesium 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 1,2-二溴乙烷 为溶剂， 反应 20.0h， 生成 (2S)-tert-butyl 2-((1R)-1-(2-(diethoxyphosphoryl)acetoxy)-2-oxocyclohex-3-en-1-yl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  合成蛇药碱生物碱的简便方法：（-）-allonorsecurinine的立体选择性全合成

  摘要：

  描述了利用经典反应（如格利雅（Grignard），阿尔多（Aldol）和霍纳-威蒂格（Horner-Wittig）反应等关键步骤，对生物碱（-）-allonorsecurinine进行简明的立体选择性全合成。

  DOI：

  10.1016/j.tetlet.2012.08.088
• 作为产物：
  描述：

  L-脯氨酸 在 碳酸氢钠 、 magnesium 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二溴乙烷 为溶剂， 反应 51.75h， 生成 N-(butyloxycarbonyl)-2(S)-(1-oxo-4-pentenyl)pyrrolidine
  参考文献：
  名称：

  合成蛇药碱生物碱的简便方法：（-）-allonorsecurinine的立体选择性全合成

  摘要：

  描述了利用经典反应（如格利雅（Grignard），阿尔多（Aldol）和霍纳-威蒂格（Horner-Wittig）反应等关键步骤，对生物碱（-）-allonorsecurinine进行简明的立体选择性全合成。

  DOI：

  10.1016/j.tetlet.2012.08.088

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.
• Synthesis and biological activity of ketomethylene-containing nonapeptide analogs of snake venom angiotensin converting enzyme inhibitors
  作者：Ronald G. Almquist、W. R. Chao、A. K. Judd、C. Mitoma、D. J. Rossi、R. E. Panasevich、R. J. Matthews

  DOI：10.1021/jm00398a012

  日期：1988.3

  Two ketomethylene-containing nonapeptide analogues were synthesized to determine if ketomethylene analogues of the nonapeptide venom inhibitors of angiotensin converting enzyme (ACE) would have oral ACE inhibition activity. Both ketomethylene-containing nonapeptides 18 and 19 were potent inhibitors of rabbit lung ACE with I50s of 3.4 and 8.0 nM, respectively, compared to 340 nM for their parent nonapeptide and 450 nM for captopril. Peptide 18 was rapidly cleaved by trypsin, but 19 was reasonably stable to all enzyme degradation systems tested with maximum degradation of 50% by pepsin in 3 h. Both 18 and 19 when given iv to normotensive rats were between 3 and 10 times more potent than captopril in inhibiting an angiotensin I induced blood pressure increase. Peptide 19 showed no ACE inhibition activity in unanesthetized normotensive rats when administered orally at doses of 10 or 100 mg/kg. Experiments were conducted to determine whether 19 is adsorbed from the gastrointestinal track following oral administration. These experiments indicated that 19 is adsorbed. It is concluded that the lack of oral activity of 19 is probably due to its rapid excretion, probably into the bile.
• A facile approach to the synthesis of securinega alkaloids: stereoselective total synthesis of (−)-allonorsecurinine
  作者：Alugubelli Sathish Reddy、Pabbaraja Srihari

  DOI：10.1016/j.tetlet.2012.08.088

  日期：2012.10

  A concise stereoselective total synthesis of alkaloid (−)-allonorsecurinine is described utilizing classical reactions such as Grignard, Aldol and Horner–Wittig reactions as the key steps.

  描述了利用经典反应（如格利雅（Grignard），阿尔多（Aldol）和霍纳-威蒂格（Horner-Wittig）反应等关键步骤，对生物碱（-）-allonorsecurinine进行简明的立体选择性全合成。