4-methyl-N-(3-octylphenyl)-N-oxiranylmethylbenzenesulfonamide | 925706-99-6

• 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: 4-methyl-N-(3-octylphenyl)-N-oxiranylmethylbenzenesulfonamide
• CAS: 925706-99-6
• 化学式: C₂₄H₃₃NO₃S
• 分子量: 415.597
• InChiKey: CHACZUJMZQEZQK-HSZRJFAPSA-N

物化性质

• 沸点：
  553.9±60.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  29.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.91
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(3-octylphenyl)-N-oxiranylmethylbenzenesulfonamide 在 palladium dihydroxide 盐酸 、 正丁基锂 、 三甲基溴硅烷 、 偶氮二甲酸二异丙酯 、 polymer-bound PPh₃ 、 二苯基膦叠氮化物 、 氨 、 氢气 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.25h， 生成 [(R)-3-Amino-4-(3-octyl-phenylamino)-butyl]-phosphonic acid; hydrobromide
  参考文献：
  名称：

  Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists

  摘要：

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.060
• 作为产物：
  描述：

  3-octylaniline 在 吡啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 4-methyl-N-(3-octylphenyl)-N-oxiranylmethylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists

  摘要：

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.060