tert-butyl (R)-(1-(benzyloxy)-3-(5-bromo-3-(2,6-difluorobenzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)carbamate | 1044526-07-9

• 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 (R)-(1-(benzyloxy)-3-(5-bromo-3-(2,6-difluorobenzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)carbamate
• CAS: 1044526-07-9
• 化学式: C₂₇H₃₀BrF₂N₃O₅
• 分子量: 594.453
• InChiKey: DLHYVBXLPYDYTJ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  91.56
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-(1-(benzyloxy)-3-(5-bromo-3-(2,6-difluorobenzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)carbamate 、 2-氟-3-甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 tert-butyl (R)-(1-(benzyloxy)-3-(3-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)carbamate
  参考文献：
  名称：

  5-Aryluracils as potent GnRH antagonists—Characterization of atropisomers

  摘要：

  Optimization of a series of uracils bearing a 2-fluoro-or 2-chloro-3-methoxyphenyl group at the 5-position resulted in compounds such as 3d and 3f with subnanomolar binding affinity at the human GnRH receptor. While the 2-fluoro-3-methoxyphenyl compound 3a was characterized as a mixture of interchangeable atropisomers, the diastereoisomers of 2-chloro-3-methoxyphenyl analogs were separated. It was found that the aR-atropisomer was much more potent than the aS-isomer based on the X-ray crystal structure of 3h-II. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.029
• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 、 5-溴-1-(2,6-二氟苄基)-6-甲基-2,4(1H,3H)-嘧啶二酮 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (R)-(1-(benzyloxy)-3-(5-bromo-3-(2,6-difluorobenzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)carbamate
  参考文献：
  名称：

  5-Aryluracils as potent GnRH antagonists—Characterization of atropisomers

  摘要：

  Optimization of a series of uracils bearing a 2-fluoro-or 2-chloro-3-methoxyphenyl group at the 5-position resulted in compounds such as 3d and 3f with subnanomolar binding affinity at the human GnRH receptor. While the 2-fluoro-3-methoxyphenyl compound 3a was characterized as a mixture of interchangeable atropisomers, the diastereoisomers of 2-chloro-3-methoxyphenyl analogs were separated. It was found that the aR-atropisomer was much more potent than the aS-isomer based on the X-ray crystal structure of 3h-II. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.029