3-[(piperidin-4-yl)methyl]benzo[d]oxazol-2(3H )-one | 1119185-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-[(piperidin-4-yl)methyl]benzo[d]oxazol-2(3H )-one
• 英文别名: 3-(Piperidin-4-ylmethyl)-1,3-benzoxazol-2-one
• CAS: 1119185-12-4
• 化学式: C₁₃H₁₆N₂O₂
• mdl: MFCD16482083
• 分子量: 232.282
• InChiKey: XLKGBLZNIXJTBA-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  369.5±34.0 °C(predicted)
• 密度：
  1.202±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(piperidin-4-yl)methyl]benzo[d]oxazol-2(3H )-one 、 1-(氯甲基)-2,4-二甲苯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以66%的产率得到3-[[1-(2,4-dimethylbenzyl)piperidin-4-yl]methyl]benzo[d]oxazol-2(3H)-one
  参考文献：
  名称：

  Substituted benzo[d]oxazol-2(3H)-one derivatives with preference for the σ1 binding site☆

  摘要：

  We describe here the synthesis and the binding interaction with sigma(1) and sigma(2) receptors of a series of new benzo[d]oxazol-2(3H)-one derivatives variously substituted on the N-benzyl moiety. The results of binding studies confirm the notion that the benzoxazolone moiety confers preference towards sigma(1) sites and establish that the ability to bind to sigma(1), but not to sigma(2) receptors, is strongly affected by the kind and the position of the substituents introduced in the N-benzyl ring. In fact, compounds with substitutions in para-position with atoms of Cl, H or F or with a CH3 group exhibit a higher affinity for sigma(1) receptors than the corresponding ortho-substituted compounds. The highest affinity and selectivity, with K-i values of 0.1 and 427 nM for sigma(1) and sigma(2) receptors, respectively, and a corresponding K-i sigma(2)/K-i sigma(1) selectivity ratio of 4270 were found for the Cl-substituted compound.These results indicate that benzo[d]oxazol-2(3H)-one derivatives are among the most selective and sigma(1) receptor-preferring ligands currently available. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.011
• 作为产物：
  描述：

  3-[[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl]benzo[d]oxazol-2(3H )-one 在 三氟乙酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 以93%的产率得到3-[(piperidin-4-yl)methyl]benzo[d]oxazol-2(3H )-one
  参考文献：
  名称：

  Substituted benzo[d]oxazol-2(3H)-one derivatives with preference for the σ1 binding site☆

  摘要：

  We describe here the synthesis and the binding interaction with sigma(1) and sigma(2) receptors of a series of new benzo[d]oxazol-2(3H)-one derivatives variously substituted on the N-benzyl moiety. The results of binding studies confirm the notion that the benzoxazolone moiety confers preference towards sigma(1) sites and establish that the ability to bind to sigma(1), but not to sigma(2) receptors, is strongly affected by the kind and the position of the substituents introduced in the N-benzyl ring. In fact, compounds with substitutions in para-position with atoms of Cl, H or F or with a CH3 group exhibit a higher affinity for sigma(1) receptors than the corresponding ortho-substituted compounds. The highest affinity and selectivity, with K-i values of 0.1 and 427 nM for sigma(1) and sigma(2) receptors, respectively, and a corresponding K-i sigma(2)/K-i sigma(1) selectivity ratio of 4270 were found for the Cl-substituted compound.These results indicate that benzo[d]oxazol-2(3H)-one derivatives are among the most selective and sigma(1) receptor-preferring ligands currently available. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.011