tert-butyl (2S,3S)-3-allyl-2-hydroxymethyl-pyrrolidine-1-carboxylate | 187409-41-2

• 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: tert-butyl (2S,3S)-3-allyl-2-hydroxymethyl-pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,3S)-2-(hydroxymethyl)-3-prop-2-enylpyrrolidine-1-carboxylate
• CAS: 187409-41-2
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: TWNVPQYVKNDIBM-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-3-allyl-2-hydroxymethyl-pyrrolidine-1-carboxylate 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以86%的产率得到(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
• 作为产物：
  描述：

  (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.75h， 生成 tert-butyl (2S,3S)-3-allyl-2-hydroxymethyl-pyrrolidine-1-carboxylate
  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

• 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