4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazineethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazineethanol
• 英文别名: 2-[4-(2,3-Dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethanol
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: VSHHOISKWZZMAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  邻苯二甲酸亚胺 、 4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazineethanol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2-{2-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-ethyl}-isoindole-1,3-dione
  参考文献：
  名称：

  A Series of N4-Imidoethyl Derivatives of 1-(2,3-Dihydro-1,4-benzodioxin-5-yl)piperazine as 5-HT1A Receptor Ligands: Synthesis and Structure-Affinity Relationships

  摘要：

  A series of unsubstituted and substituted succinimido, maleimido, and glutarimidoethyl derivatives of eltoprazine (3) was synthesized and tested for affinity for the 5-HT1A receptor in rat brain homogenates. The unsubstituted compounds have a moderate affinity for the receptor, while the affinity considerably increases by substitution at or enlargement of these cyclic ring systems. A good correlation was found between the inhibition constant K-i (expressed as pK(i)) and the lipophilicity (clogP). No correlation was observed between the pK(i) or pK(i)(+) (local. inhibition constant) and the basicity of the N4-nitrogen atom.

  DOI：

  10.1021/jm00021a020
• 作为产物：
  描述：

  1-(2,3-二氢-1,4-苯并二烷-5-基)哌嗪盐酸盐 、 2-氯乙醇 在 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以78%的产率得到4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazineethanol
  参考文献：
  名称：

  A Series of N4-Imidoethyl Derivatives of 1-(2,3-Dihydro-1,4-benzodioxin-5-yl)piperazine as 5-HT1A Receptor Ligands: Synthesis and Structure-Affinity Relationships

  摘要：

  A series of unsubstituted and substituted succinimido, maleimido, and glutarimidoethyl derivatives of eltoprazine (3) was synthesized and tested for affinity for the 5-HT1A receptor in rat brain homogenates. The unsubstituted compounds have a moderate affinity for the receptor, while the affinity considerably increases by substitution at or enlargement of these cyclic ring systems. A good correlation was found between the inhibition constant K-i (expressed as pK(i)) and the lipophilicity (clogP). No correlation was observed between the pK(i) or pK(i)(+) (local. inhibition constant) and the basicity of the N4-nitrogen atom.

  DOI：

  10.1021/jm00021a020

文献信息

• US5710149A
  申请人：——

  公开号：US5710149A

  公开（公告）日：1998-01-20
• A Series of N4-Imidoethyl Derivatives of 1-(2,3-Dihydro-1,4-benzodioxin-5-yl)piperazine as 5-HT1A Receptor Ligands: Synthesis and Structure-Affinity Relationships
  作者：B. J. van Steen、I. van Wijngaarden、M. Th. M. Tulp、W. Soudijn

  DOI：10.1021/jm00021a020

  日期：1995.10

  A series of unsubstituted and substituted succinimido, maleimido, and glutarimidoethyl derivatives of eltoprazine (3) was synthesized and tested for affinity for the 5-HT1A receptor in rat brain homogenates. The unsubstituted compounds have a moderate affinity for the receptor, while the affinity considerably increases by substitution at or enlargement of these cyclic ring systems. A good correlation was found between the inhibition constant K-i (expressed as pK(i)) and the lipophilicity (clogP). No correlation was observed between the pK(i) or pK(i)(+) (local. inhibition constant) and the basicity of the N4-nitrogen atom.