tert-butyl N-[(1R)-1-[(2R)-4-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl]carbamate | 524018-08-4

• 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: tert-butyl N-[(1R)-1-[(2R)-4-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl]carbamate
• CAS: 524018-08-4
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: HOEJRANUPVSCAK-HZPDHXFCSA-N

物化性质

• 沸点：
  467.0±24.0 °C(predicted)
• 密度：
  1.139±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 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：

  tert-butyl N-[(1R)-1-[(2R)-4-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl]carbamate 在 四(三苯基膦)钯 溴 、 L-Selectride 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 [1-(4-oxo-5-pyrimidin-5-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：

  1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 、 N-Boc-D-苯丙氨醛 在 lithium perchlorate 作用下， 以 乙醚 为溶剂， 生成 tert-butyl N-[(1R)-1-[(2R)-4-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl]carbamate
  参考文献：
  名称：

  Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors

  摘要：

  We have prepared novel peptidomimetics based on a 2,4,6-trisubstituted tetrahydropyran. This scaffold was constructed in an isosteric transformation using conceptual constraints imposed on a tripeptide moiety involving O-i'-C-1(+1)gamma and O-i'-Ni+2 formal cyclization modes. A series of regioselective transformations commencing with a substituted dihydropyran-4-one readily provided the required analogues. Specific tetrahydropyrane analogues modeled on PheArgTrp as a truncated version of the melanocortin receptor message sequence, showed activity at the melanocortin receptors MC4R and MC1R. Thus, the 2,4,6-trisubstituted tetrahydropyran scaffold has provided a potentially useful peptidomimetic lead, and conceptual cyclization of peptide moieties can offer a valuable design strategy in peptidomimetic research. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00274-8