(2S,3S)-3-allyl-N-(tert-butyloxycarbonyl)proline | 187409-44-5

• 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,3S)-3-allyl-N-(tert-butyloxycarbonyl)proline
• 英文别名: (2s,3s)-N-boc-3-allylproline；(2S,3S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-3-prop-2-enylpyrrolidine-2-carboxylic acid
• CAS: 187409-44-5
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: ZCQMKSFGYOUZLD-UWVGGRQHSA-N

物化性质

• 沸点：
  369.3±35.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-allyl-N-(tert-butyloxycarbonyl)proline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以89%的产率得到N-<(tert-butyloxy)carbonyl>-trans-3-n-propyl-L-proline
  参考文献：
  名称：

  光学纯的顺式和反式3-取代脯氨酸衍生物的新型立体发散性合成。

  摘要：

  DOI：

  10.1021/jo961790r
• 作为产物：
  描述：

  (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 在 chromium(VI) oxide 、 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 3.75h， 生成 (2S,3S)-3-allyl-N-(tert-butyloxycarbonyl)proline
  参考文献：
  名称：

  光学纯的顺式和反式3-取代脯氨酸衍生物的新型立体发散性合成。

  摘要：

  DOI：

  10.1021/jo961790r

文献信息

• Novel compounds of proline and morpholine derivatives
  申请人：Cheng Hengmiao

  公开号：US20050261290A1

  公开（公告）日：2005-11-24

  The present invention relates to compounds with the formulas (I), (II), and (III), or a pharmaceutically acceptable salt thereof: wherein T is a (4 to 10)-membered heterocyclyl selected from the group consisting of and wherein R 1 , R 2 and R 3 are as defined in the specification. The invention also relates to pharmaceutical compositions comprising the compounds of formulas (I), (II), and (III) and methods of treating a condition that is mediated by the modulation of the 11-β-hsd-1 enzyme, the method comprising administering to a mammal an effective amount of a compound of formulas (I), (II), and (III).

  本发明涉及以下式子（I），（II）和（III）或其药学上可接受的盐的化合物：其中T是从以下组中选择的（4到10）成员杂环基：其中R1，R2和R3如规范中所定义。本发明还涉及包括式子（I），（II）和（III）化合物的药物组合物以及治疗通过调节11-β-hsd-1酶介导的疾病的方法，该方法包括向哺乳动物中投与式子（I），（II）和（III）化合物的有效量。
• Molecular Building Kit of Fused-Proline-Derived Peptide Mimetics Allowing Specific Adjustment of the Dihedral Ψ Angle
  作者：Juergen Einsiedel、Harald Lanig、Reiner Waibel、Peter Gmeiner

  DOI：10.1021/jo701703e

  日期：2007.11.1

  [Graphics]Proline-derived peptide mimetics have become an area of paramount importance in peptide and protein chemistry. Since protein crystal structures frequently display W angles of 140-170 degrees for prolyl moieties, our intention was to design a completely novel series of 2,3-fused-proline-derived lactams covering this particular conformational space. Extending our recently described toolset of spirocyclic reverse-turn mimetics, we synthesized pyrrolidinyl-fused seven-, eight-, and nine-membered unsaturated lactam model peptides taking advantage of Grubbs' ring-closing metathesis. Investigating the seven-membered lactam 3a by means of IR and NMR spectroscopy and semiempirical molecular dynamics simulations, we could not observe a U-turn conformation; however, increasing the ring size to give eight- and nine-membered congeners revealed moderate and high type II P-turn inducing properties. Interestingly, the conformational properties of our model systems depend on both the ring size of the fused dehydro-Freidinger lactam and the position of the endocyclic double bond. Superior reverse-turn inducing properties could be observed for the fused azacyclononenone 3e. According to diagnostic transanular NOEs, a discrete folding principle of the lactam ring strongly deviating from the regioisomeric lactams 3c,f explains the conformational behavior. Hence, we were able to establish a molecular building kit that allows adjustments of a wide range of naturally occurring proline W angles and thus can be exploited to probe molecular recognition and functional properties of biological systems.
• A Novel Stereodivergent Synthesis of Optically Pure <i>cis</i>- and <i>trans</i>-3-Substituted Proline Derivatives
  作者：N. André Sasaki、Michael Dockner、Angèle Chiaroni、Claude Riche、Pierre Potier

  DOI：10.1021/jo961790r

  日期：1997.2.1