(S)-2-苯甲酰基吡咯烷-1-羧酸叔丁酯 | 111492-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-2-苯甲酰基吡咯烷-1-羧酸叔丁酯
• 英文名称: tert-butyl (S)-2-benzoylpyrrolidine-1-carboxylate
• 英文别名: (S)-tert-butyl 2-benzoylpyrrolidine-1-carboxylate；1-Pyrrolidinecarboxylic acid, 2-benzoyl-, 1,1-dimethylethyl ester, (2S)-；tert-butyl (2S)-2-benzoylpyrrolidine-1-carboxylate
• CAS: 111492-61-6
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: XJQDKMPOKJENLS-ZDUSSCGKSA-N

物化性质

• 沸点：
  385.1±35.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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)-2-苯甲酰基吡咯烷-1-羧酸叔丁酯 在 三氟乙酸 作用下， 生成 (S)-phenyl(pyrrolidin-2-yl)methanone
  参考文献：
  名称：

  酮吡咯烷和酮氮杂环丁烷作为有效的二肽基肽酶IV（DPP IV）抑制剂。

  摘要：

  在本文中，讨论了两类基于亲电子试剂的二肽基肽酶IV（DPP IV）抑制剂，酮吡咯烷和酮氮杂环丁烷的合成和构效关系（SAR）。这些系列的SAR表明，2-噻唑，2-苯并噻唑和2-吡啶基酮是针对DPP IV效力的最佳S1'结合基团。此外，环己基甘氨酸（CHG）和八氢吲哚羧酸酯（OIC）均是每个系列中最有效的S2结合基团。在中心环的α位的立体化学与酮吡咯烷系列中的效力有关，但与酮氮杂环丁烷系列中的效力无关。最后，酮氮杂环丁烷比相应的酮吡咯烷烷显示出增强的稳定性，同时保持它们的效力。实际上，

  DOI：

  10.1016/j.bmcl.2004.08.057
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 (S)-2-苯甲酰基吡咯烷-1-羧酸叔丁酯
  参考文献：
  名称：

  4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors

  摘要：

  New 4-phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines were synthesized. Their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. In the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were the best inhibitors having IC50 values of 30 and 23 nM, respectively. This series of compounds shows that that P1 pyrrolidine ring, which is common in most POP inhibitors, can be replaced by either a cyclopentyl ring or a phenyl ring, causing only a slight decrease in the inhibitory activity. In the series of 4-phenylbutanoyl-L-prolyl-2(S)- acyl-pyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were not as active as in the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, The hydroxyacetyl derivative did however show high inhibitors activity. This compound is structurally similar to JTP-4819, which is one of the most potent prolyl oligopeptidase inhibitors. The acyl group in the two series of new compounds seems to bind to different sites of the enzyme, since the second series of ne compounds did not show the same cyclopentanecarbonyl or benzoyl specificity as the first series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00061-5

文献信息

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  DOI：10.1021/jacs.6b00100

  日期：2016.2.24

  placement of fluorine substituents in the chiral ligand. This approach has led to a new, second-generation family of chiral oxazaborolidinium cationic species which can be used to effect many Diels-Alder reactions in >95% yield and >95% ee using catalyst loadings at the 1-2 mol % level. The easy recovery of the chiral ligand makes the application of these new catalysts especially attractive for large-scale

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  DOI：10.1021/acs.orglett.9b01782

  日期：2019.8.2

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  DOI：10.1021/acs.joc.0c01764

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  DOI：10.1021/acs.orglett.9b00031

  日期：2019.2.1

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  DOI：10.1002/cssc.201802815

  日期：2019.3.21

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