[(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-phenoxyethylamine | 522616-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-phenoxyethylamine
• 英文别名: (2,2-diphenyl[1,3]dioxolan-4-ylmethyl)(2-phenoxyethyl)amine；N-[(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-phenoxyethanamine
• CAS: 522616-89-3
• 化学式: C₂₄H₂₅NO₃
• 分子量: 375.467
• InChiKey: NNVMIQMBTAAZFU-UHFFFAOYSA-N

物化性质

• 沸点：
  524.7±50.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-phenoxyethylamine 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 65.0h， 生成 (2,2-diphenyl[1,3]dioxolan-4-ylmethyl)methyl(2-phenoxyethyl)ammonium iodide
  参考文献：
  名称：

  1,3-Dioxolane-Based Ligands as a Novel Class of α₁-Adrenoceptor Antagonists

  摘要：

  1,3-Dioxolane-based compounds (2-14) were synthesized, and the pharmacological profiles at alpha(1)-adrenoceptor subtypes were assessed by functional experiments in isolated rat vas deferens (alpha(1A)), spleen (alpha(1B)), and aorta (alpha(1D)). Compound 9, with a pA(2) of 7.53, 7.36, and 8.65 at alpha(1A), alpha(1B), and alpha(1D)), respectively, is the most potent antagonist of the series, while compound 10 with a pA(2) of 8.37 at alpha(1D) subtype and selectivity ratios of 162 (alpha(1D)/alpha(1A)) and 324 (alpha(1D))/alpha(1B)) is the most selective. Binding assays in CHO cell membranes expressing human cloned alpha(1)-adrenoceptor subtypes confirm the pharmacological profiles derived from functional experiments, although the selectivity values are somewhat lower. Therefore, it is concluded that 1,3-dioxolane-based ligands are a new class of alpha(1)-adrenoceptor antagonists.

  DOI：

  10.1021/jm021078o
• 作为产物：
  描述：

  苯氧乙酰胺 在 dimethyl sulfide borane 、 potassium iodide 作用下， 以 乙二醇甲醚 、 二乙二醇二甲醚 为溶剂， 反应 18.0h， 生成 [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-phenoxyethylamine
  参考文献：
  名称：

  1,3-Dioxolane-Based Ligands as a Novel Class of α₁-Adrenoceptor Antagonists

  摘要：

  1,3-Dioxolane-based compounds (2-14) were synthesized, and the pharmacological profiles at alpha(1)-adrenoceptor subtypes were assessed by functional experiments in isolated rat vas deferens (alpha(1A)), spleen (alpha(1B)), and aorta (alpha(1D)). Compound 9, with a pA(2) of 7.53, 7.36, and 8.65 at alpha(1A), alpha(1B), and alpha(1D)), respectively, is the most potent antagonist of the series, while compound 10 with a pA(2) of 8.37 at alpha(1D) subtype and selectivity ratios of 162 (alpha(1D)/alpha(1A)) and 324 (alpha(1D))/alpha(1B)) is the most selective. Binding assays in CHO cell membranes expressing human cloned alpha(1)-adrenoceptor subtypes confirm the pharmacological profiles derived from functional experiments, although the selectivity values are somewhat lower. Therefore, it is concluded that 1,3-dioxolane-based ligands are a new class of alpha(1)-adrenoceptor antagonists.

  DOI：

  10.1021/jm021078o

文献信息

• Enantiomeric resolution of [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl](2-phenoxyethyl)amine, a potent α₁and 5-HT_1Areceptor ligand: an in vitro and computational study
  作者：Silvia Franchini、Annamaria Baraldi、Claudia Sorbi、Federica Pellati、Elena Cichero、Umberto M. Battisti、Piero Angeli、Antonio Cilia、Livio Brasili

  DOI：10.1039/c4md00484a

  日期：——

  Enantioseparation and stereoselective synthesis of (1), a potent 5-HT_1AR ligand, were performed. Surprisingly, the enantiomers proved to be equipotent.

  对(1)进行对映体分离和立体选择性合成，该化合物是一种有效的5-HT_1AR配体。令人惊讶的是，这两个对映体的效力相当。
• 1,3-Dioxolane-Based Ligands as a Novel Class of α₁-Adrenoceptor Antagonists
  作者：Livio Brasili、Claudia Sorbi、Silvia Franchini、Massimo Manicardi、Piero Angeli、Gabriella Marucci、Amedeo Leonardi、Elena Poggesi

  DOI：10.1021/jm021078o

  日期：2003.4.1

  1,3-Dioxolane-based compounds (2-14) were synthesized, and the pharmacological profiles at alpha(1)-adrenoceptor subtypes were assessed by functional experiments in isolated rat vas deferens (alpha(1A)), spleen (alpha(1B)), and aorta (alpha(1D)). Compound 9, with a pA(2) of 7.53, 7.36, and 8.65 at alpha(1A), alpha(1B), and alpha(1D)), respectively, is the most potent antagonist of the series, while compound 10 with a pA(2) of 8.37 at alpha(1D) subtype and selectivity ratios of 162 (alpha(1D)/alpha(1A)) and 324 (alpha(1D))/alpha(1B)) is the most selective. Binding assays in CHO cell membranes expressing human cloned alpha(1)-adrenoceptor subtypes confirm the pharmacological profiles derived from functional experiments, although the selectivity values are somewhat lower. Therefore, it is concluded that 1,3-dioxolane-based ligands are a new class of alpha(1)-adrenoceptor antagonists.