(R)-2-(4-octylphenoxymethyl)oxirane | 925706-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-(4-octylphenoxymethyl)oxirane
• 英文别名: (2R)-2-[(4-octylphenoxy)methyl]oxirane
• CAS: 925706-87-2
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: DEVITEWVQCISFK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(4-octylphenoxymethyl)oxirane 在 正丁基锂 、 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 [(S)-3-azido-4-(-4-octylphenoxy)butyl]phosphonic acid diethyl ester
  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：

  4-辛基酚 、 (S)-缩水甘油 在 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 24.0h， 以84%的产率得到(R)-2-(4-octylphenoxymethyl)oxirane
  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

文献信息

• Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists
  作者：Frank W. Foss、Ashley H. Snyder、Michael D. Davis、Michael Rouse、Mark D. Okusa、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1016/j.bmc.2006.10.060

  日期：2007.1

  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.