2-[4-(2-Azidoethoxy)-3-fluorophenyl]propanoic acid | 1391848-26-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-[4-(2-Azidoethoxy)-3-fluorophenyl]propanoic acid
• CAS: 1391848-26-2
• 化学式: C₁₁H₁₂FN₃O₃
• 分子量: 253.233
• InChiKey: WZEPHHYPJYJGGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[4-(2-Azidoethoxy)-3-fluorophenyl]propanoic acid 、 4-叔-丁基苄胺 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2-[4-(2-aminoethoxy)-3-fluorophenyl]-N-[(4-tert-butylphenyl)methyl]propanamide
  参考文献：
  名称：

  The SAR analysis of TRPV1 agonists with the α-methylated B-region

  摘要：

  A series of TRPV1 agonists with amide, reverse amide, and thiourea groups in the B-region and their corresponding alpha-methylated analogues were investigated. Whereas the alpha-methylation of the amide B-region enhanced the binding affinities and potencies as agonists, that of the reverse amide and thiourea led to a reduction in receptor affinity. The analysis indicated that proper hydrogen bonding as well as steric effects in the B-region are critical for receptor binding. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.059
• 作为产物：
  描述：

  3-氟-4-羟基苯乙酸 在 sodium azide 、 硫酸 、 四丁基溴化铵 、 水 、 sodium hydride 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 9.0h， 生成 2-[4-(2-Azidoethoxy)-3-fluorophenyl]propanoic acid
  参考文献：
  名称：

  The SAR analysis of TRPV1 agonists with the α-methylated B-region

  摘要：

  A series of TRPV1 agonists with amide, reverse amide, and thiourea groups in the B-region and their corresponding alpha-methylated analogues were investigated. Whereas the alpha-methylation of the amide B-region enhanced the binding affinities and potencies as agonists, that of the reverse amide and thiourea led to a reduction in receptor affinity. The analysis indicated that proper hydrogen bonding as well as steric effects in the B-region are critical for receptor binding. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.059