3,5-di-phenethyl-4,5-dihydroisoxazole | 1036384-53-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3,5-di-phenethyl-4,5-dihydroisoxazole
• 英文别名: 3,5-diphenethyl-4,5-dihydroisoxazole；3,5-Bis(2-phenylethyl)-4,5-dihydro-1,2-oxazole
• CAS: 1036384-53-8
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: ANJNUYIYHJBLQF-UHFFFAOYSA-N

物化性质

• 熔点：
  56.2-58.0 °C
• 沸点：
  415.5±38.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-di-phenethyl-4,5-dihydroisoxazole 在 氢气 、 镍 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以85%的产率得到5-hydroxy-1,7-diphenylheptan-3-one
  参考文献：
  名称：

  Synthesis and Evaluation of Estrogen Agonism of Diaryl 4,5-Dihydroisoxazoles, 3-Hydroxyketones, 3-Methoxyketones, and 1,3-Diketones: A Compound Set Forming a 4D Molecular Library

  摘要：

  In this paper, the preparation and systematic evaluation of estrogen receptor alpha (ER alpha) and estrogen receptor beta (ER beta) activities of some diaryl-1,3-diones and their synthetic intermediates, diaryl-4,5-dihydroisoxazoles, diaryl-3-hydroxyketones, diaryl-3-methoxyketones, and diaryl-2-(dimethyl-lambda(4)-sulfanylidene)-1,3-diones, is described. The set of 72 compounds constitutes a general schematic structure aryl1-linker1-spacer-linker2-aryl2, where the linker1-spacer-linker2 length varies between 4 and 8 carbons. The set of compounds was applied here to map and explore the active sites of subtypes ER alpha and ER beta. The highest activities were obtained with dihydroisoxazole and hydroxyketone spacers, but even the most flexible diones with unsubstituted aryl groups showed some agonism. Most compounds were found to be ER alpha selective or to activate both receptors, but in some cases we saw also clearly stronger ER beta activation.

  DOI：

  10.1021/jm8001795
• 作为产物：
  描述：

  5-hydroxy-1,7-diphenylheptan-3-one 在 吡啶 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 3,5-di-phenethyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  从 β-羟基酮中立体选择性地制备 ACYCLICsyn-1,3-氨基醇

  摘要：

  通过使用氢化铝锂对衍生自无环 β-羟基酮的 β-羟基酮-O-苄肟进行立体选择性还原，可以高产率地制备合成-1,3-氨基醇。

  DOI：

  10.1246/cl.1984.147

文献信息

• [EN] NOVEL 4,5-DIHYDROISOXAZOLES WITH ESTROGENIC ACTIVITY<br/>[FR] NOUVEAUX 4,5-DIHYDROISOXAZOLES AVEC UNE ACTIVITÉ OETROGÉNIQUE
  申请人：PULKKINEN JUHA

  公开号：WO2009066009A1

  公开（公告）日：2009-05-28

  This invention relates to novel 4,5-dihydroisoxazoles of formula (I), to their use as estrogen receptor modulators, and to methods of their preparation.

  该发明涉及新型的4,5-二氢异噁唑（I）的公式，以及它们作为雌激素受体调节剂的用途，以及它们的制备方法。
• NOVEL 4,5-DIHYDROISOXAZOLES WITH ESTROGENIC ACTIVITY
  申请人：Pulkkinen, Juha

  公开号：EP2222653A1

  公开（公告）日：2010-09-01
• Synthesis and Evaluation of Estrogen Agonism of Diaryl 4,5-Dihydroisoxazoles, 3-Hydroxyketones, 3-Methoxyketones, and 1,3-Diketones: A Compound Set Forming a 4D Molecular Library
  作者：Juha T. Pulkkinen、Paavo Honkakoski、Mikael Peräkylä、Istvan Berczi、Reino Laatikainen

  DOI：10.1021/jm8001795

  日期：2008.6.1

  In this paper, the preparation and systematic evaluation of estrogen receptor alpha (ER alpha) and estrogen receptor beta (ER beta) activities of some diaryl-1,3-diones and their synthetic intermediates, diaryl-4,5-dihydroisoxazoles, diaryl-3-hydroxyketones, diaryl-3-methoxyketones, and diaryl-2-(dimethyl-lambda(4)-sulfanylidene)-1,3-diones, is described. The set of 72 compounds constitutes a general schematic structure aryl1-linker1-spacer-linker2-aryl2, where the linker1-spacer-linker2 length varies between 4 and 8 carbons. The set of compounds was applied here to map and explore the active sites of subtypes ER alpha and ER beta. The highest activities were obtained with dihydroisoxazole and hydroxyketone spacers, but even the most flexible diones with unsubstituted aryl groups showed some agonism. Most compounds were found to be ER alpha selective or to activate both receptors, but in some cases we saw also clearly stronger ER beta activation.
• STEREOSELECTIVE PREPARATION OF ACYCLIC<i>syn</i>-1,3-AMINO ALCOHOLS FROM β-HYDROXY KETONES
  作者：Koichi Narasaka、Yutaka Ukaji

  DOI：10.1246/cl.1984.147

  日期：1984.1.5

  syn-1,3-Amino alcohols are prepared in good yields by the stereoselective reduction of β-hydroxy ketone-O-benzyloximes derived from acyclic β-hydroxy ketones with lithium aluminium hydride.

  通过使用氢化铝锂对衍生自无环 β-羟基酮的 β-羟基酮-O-苄肟进行立体选择性还原，可以高产率地制备合成-1,3-氨基醇。