N-[(benzyloxy)carbonyl]-D-aspartic acid β-tert-butyl ester α-{[(R)-1-(trifluoromethyl)phenyl]ethyl}amide | 911069-02-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(benzyloxy)carbonyl]-D-aspartic acid β-tert-butyl ester α-{[(R)-1-(trifluoromethyl)phenyl]ethyl}amide
• 英文别名: N-benzyloxycarbonyl-D-aspartic acid β-tert-butyl ester α-[(R)-1-(3-trifluoromethylphenyl)ethyl]amide；N-benzyloxycarbonyl-D-aspartic acid β-t-butyl ester α-[(R)-1-(3-trifluoromethylphenyl)ethyl]amide；N-benzyloxycarbonyl-D-aspartic acid β-tert-butyl ester α-[(R)-1-(3-trifluoromethylphenyl)ethyl] amide；N-benzyloxycarbonyl-D-aspartic acid β-t-butyl ester α-[(R)-1(3-trifluoromethylphenyl)ethyl]amide
• CAS: 911069-02-8
• 化学式: C₂₅H₂₉F₃N₂O₅
• 分子量: 494.511
• InChiKey: LOGLZHMLMWBPMR-OXQOHEQNSA-N

物化性质

• 沸点：
  627.0±55.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[(benzyloxy)carbonyl]-D-aspartic acid β-tert-butyl ester α-{[(R)-1-(trifluoromethyl)phenyl]ethyl}amide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到Butanoic acid,3-amino-4-oxo-4-[[(1R)-1-[3-(trifluoromethyl)phenyl]ethyl]amino]-,1,1-dimethylethyl ester, (3R)-
  参考文献：
  名称：

  Azetidinones as vasopressin V1a antagonists

  摘要：

  The azetidinone LY307174 (1) was identified as a screening lead for the vasopressin V1a receptor (IC50 45 nM at the human V1a receptor) based on molecular similarity to ketoconazole (2), a known antagonist of the luteinizing hormone releasing hormone receptor. Structure-activity relationships for the series were explored to optimize receptor affinity and pharmacokinetic properties, resulting in compounds with K-i values < 1 nM and brain levels after oral dosing similar to 100-fold higher than receptor affinities.[GRAPHICS](c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.031
• 作为产物：
  描述：

  (R)-1-[3-(三氟甲基)苯基]乙胺 、 Cbz-D-天冬氨酸 4-叔丁酯一水物 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-[(benzyloxy)carbonyl]-D-aspartic acid β-tert-butyl ester α-{[(R)-1-(trifluoromethyl)phenyl]ethyl}amide
  参考文献：
  名称：

  Azetidinones as vasopressin V1a antagonists

  摘要：

  The azetidinone LY307174 (1) was identified as a screening lead for the vasopressin V1a receptor (IC50 45 nM at the human V1a receptor) based on molecular similarity to ketoconazole (2), a known antagonist of the luteinizing hormone releasing hormone receptor. Structure-activity relationships for the series were explored to optimize receptor affinity and pharmacokinetic properties, resulting in compounds with K-i values < 1 nM and brain levels after oral dosing similar to 100-fold higher than receptor affinities.[GRAPHICS](c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.031