[1-(5-bromo-4-oxo-3,4-dihydro-2H-pyran-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester | 524018-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-(5-bromo-4-oxo-3,4-dihydro-2H-pyran-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R)-1-[(2R)-5-bromo-4-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl]carbamate
• CAS: 524018-10-8
• 化学式: C₁₈H₂₂BrNO₄
• 分子量: 396.281
• InChiKey: YHXDHYYTMOYONV-GDBMZVCRSA-N

物化性质

• 沸点：
  488.5±45.0 °C(predicted)
• 密度：
  1.362±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(5-bromo-4-oxo-3,4-dihydro-2H-pyran-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 在 四(三苯基膦)钯 四丁基碘化铵 、 L-Selectride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 {(R)-1-[(2R,4S,5R)-4-(Naphthalen-2-ylmethoxy)-5-pyridin-3-yl-tetrahydro-pyran-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans as Peptidomimetic Scaffolds for Melanocortin Receptor Ligands

  摘要：

  We have synthesized a series of 2,4,5-trisubstituted tetrahydropyran derivatives to determine the utility of this scaffold as a peptidomimetic platform. The key synthetic steps involved a palladium-mediated cross-coupling reaction of a dihydropyran-4-one moiety to introduce R-2 followed by a sequential regio- and diastereoselective reduction of sp(2) carbon centers. Selected compounds have shown biological activity at melanocortin receptors, indicating that this scaffold may be useful in the design of peptidomimetics relating to a tripeptide structure.

  DOI：

  10.1021/ol027281v
• 作为产物：
  描述：

  tert-butyl N-[(1R)-1-[(2R)-4-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl]carbamate 在 溴 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以70%的产率得到[1-(5-bromo-4-oxo-3,4-dihydro-2H-pyran-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans as Peptidomimetic Scaffolds for Melanocortin Receptor Ligands

  摘要：

  We have synthesized a series of 2,4,5-trisubstituted tetrahydropyran derivatives to determine the utility of this scaffold as a peptidomimetic platform. The key synthetic steps involved a palladium-mediated cross-coupling reaction of a dihydropyran-4-one moiety to introduce R-2 followed by a sequential regio- and diastereoselective reduction of sp(2) carbon centers. Selected compounds have shown biological activity at melanocortin receptors, indicating that this scaffold may be useful in the design of peptidomimetics relating to a tripeptide structure.

  DOI：

  10.1021/ol027281v

文献信息

• Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans as Peptidomimetic Scaffolds for Melanocortin Receptor Ligands
  作者：Anna Kulesza、Frank H. Ebetino、Rajesh K. Mishra、Doreen Cross-Doersen、Adam W. Mazur

  DOI：10.1021/ol027281v

  日期：2003.4.1

  We have synthesized a series of 2,4,5-trisubstituted tetrahydropyran derivatives to determine the utility of this scaffold as a peptidomimetic platform. The key synthetic steps involved a palladium-mediated cross-coupling reaction of a dihydropyran-4-one moiety to introduce R-2 followed by a sequential regio- and diastereoselective reduction of sp(2) carbon centers. Selected compounds have shown biological activity at melanocortin receptors, indicating that this scaffold may be useful in the design of peptidomimetics relating to a tripeptide structure.