1-[2-(苯氧基)乙基]-4-苯基哌嗪 | 1037-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-[2-(苯氧基)乙基]-4-苯基哌嗪
• 英文名称: 1-(2-phenoxyethyl)-4-phenylpiperazine
• 英文别名: LASSBio-728；1-(2-phenoxy-ethyl)-4-phenyl-piperazine；1-(2-Phenoxy-aethyl)-4-phenyl-piperazin；N-Phenyl-N'-(2-phenoxy-ethyl)-piperazin
• CAS: 1037-20-3
• 化学式: C₁₈H₂₂N₂O
• mdl: MFCD00419503
• 分子量: 282.385
• InChiKey: UVMOXXAVDKCMPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为产物：
  描述：

  己二酸,聚合2,2-二甲基-1,3-丙二醇和2,5-呋喃二酮,苯酸酯 在 lithium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 1-[2-(苯氧基)乙基]-4-苯基哌嗪
  参考文献：
  名称：

  Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties

  摘要：

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.032

文献信息

• N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of <i>N</i>-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines
  作者：Dmitry I. Bugaenko、Marina A. Yurovskaya、Alexander V. Karchava

  DOI：10.1021/acs.orglett.8b02676

  日期：2018.10.19

  Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The

  以DABCO为底物，引入芳基（间苯二甲氧基）碘鎓三氟甲磺酸酯作为叔sp 3-氮的芳基化剂。温和的条件和芳基转移的出色选择性使得可以获得具有不同电子性质的取代基的空前的N-芳基-DABCO盐。这种无金属的方法与已知的基于过渡金属的反应没有相似之处。已证明分离的N-芳基-DABCO盐可用于制备氟班色林。
• Adrenergic Blocking Agents. II. Piperazines¹
  作者：Ansel P. Swain、Sara K. Naegele

  DOI：10.1021/ja01649a024

  日期：1954.10
• Unsymmetrical n, n'-substituted ethylenediamine and piperazine compounds
  申请人：MCNEILAB INC

  公开号：US02695295A1

  公开（公告）日：1954-11-23