[1-(4-cyanomethylene-5-naphthalen-2-yl-tetrahydro-pyran-2-yl)-2-(4-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester | 524018-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1-(4-cyanomethylene-5-naphthalen-2-yl-tetrahydro-pyran-2-yl)-2-(4-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester
• CAS: 524018-29-9
• 化学式: C₃₀H₃₁FN₂O₃
• 分子量: 486.586
• InChiKey: QUYROTKQZSPWQM-UPRLRBBYSA-N

物化性质

• 沸点：
  674.4±55.0 °C(predicted)
• 密度：
  1.211±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.35
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [1-(4-cyanomethylene-5-naphthalen-2-yl-tetrahydro-pyran-2-yl)-2-(4-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester 在 镍 、 palladium dichloride ammonium hydroxide 、 sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 [(R)-1-[(2R,4S,5R)-4-(2-Amino-ethyl)-5-naphthalen-2-yl-tetrahydro-pyran-2-yl]-2-(4-fluoro-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 四(三苯基膦)钯 溴 、 L-Selectride 、 sodium hydride 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 苯 为溶剂， 反应 8.5h， 生成 [1-(4-cyanomethylene-5-naphthalen-2-yl-tetrahydro-pyran-2-yl)-2-(4-fluoro-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