t-butyl (R)-(1-((4-decylphenyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate | 448959-73-7

• 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: t-butyl (R)-(1-((4-decylphenyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate
• 英文别名: [(R)-1-(4-Decyl-phenylcarbamoyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester；tert-butyl N-[(2R)-1-(4-decylanilino)-3-hydroxy-1-oxopropan-2-yl]carbamate
• CAS: 448959-73-7
• 化学式: C₂₄H₄₀N₂O₄
• 分子量: 420.593
• InChiKey: CHVHGSCTJCYPNG-OAQYLSRUSA-N

物化性质

• 沸点：
  599.8±50.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  t-butyl (R)-(1-((4-decylphenyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate 在 四氮唑 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 [(R)-1-(4-Decyl-phenylcarbamoyl)-2-(di-tert-butoxy-phosphoryloxy)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of para-Alkyl aryl amide analogues of sphingosine-1-phosphate: discovery of potent S1P receptor agonists

  摘要：

  Sphingosine-1-phosphate (S1P) is a biologically active lysophospholipid with the capacity to induce a broad range of cellular responses via its interaction with the S1P family of G-protein coupled receptors. This report describes the synthesis of several potent S1P receptor agonists. For instance, compound 9c displayed an EC50=8.6 nM at the S1P(1) receptor using a [gamma-S-35]GTP binding assay as compared to an EC50=4.5 nM for the endogenous ligand. We also report the effects associated with introduction of a phenyl ring between the 'linker' and 'lipophilic tail' regions of the analogues, for example total loss of activity at S1P(2) and increased agonism at S1P(5). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00812-6
• 作为产物：
  描述：

  4-癸基苯胺 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 t-butyl (R)-(1-((4-decylphenyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis of para-Alkyl aryl amide analogues of sphingosine-1-phosphate: discovery of potent S1P receptor agonists

  摘要：

  Sphingosine-1-phosphate (S1P) is a biologically active lysophospholipid with the capacity to induce a broad range of cellular responses via its interaction with the S1P family of G-protein coupled receptors. This report describes the synthesis of several potent S1P receptor agonists. For instance, compound 9c displayed an EC50=8.6 nM at the S1P(1) receptor using a [gamma-S-35]GTP binding assay as compared to an EC50=4.5 nM for the endogenous ligand. We also report the effects associated with introduction of a phenyl ring between the 'linker' and 'lipophilic tail' regions of the analogues, for example total loss of activity at S1P(2) and increased agonism at S1P(5). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00812-6

文献信息

• [EN] NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS<br/>[FR] NOUVEAUX ANTAGONISTES SELECTIFS DU RECEPTEUR DE L'ACIDE LYSOPHOSPHATIDIQUE
  申请人：UNIV VIRGINIA

  公开号：WO2005115150A3

  公开（公告）日：2006-05-04