4-hydroxy-1,4-diphenyl-butan-2-one | 84801-97-8

• 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: 4-hydroxy-1,4-diphenyl-butan-2-one
• 英文别名: 4-Hydroxy-1,4-diphenyl-2-butanone；4-hydroxy-1,4-diphenylbutan-2-one
• CAS: 84801-97-8
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: MHWPULQIWQNQML-UHFFFAOYSA-N

物化性质

• 沸点：
  394.3±27.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二甲基硫 、 4-hydroxy-1,4-diphenyl-butan-2-one 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到2-(dimethyl-λ4-sulfanylidene)-1,4-diphenyl-butane-1,3-dione
  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：

  在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 4-hydroxy-1,4-diphenyl-butan-2-one
  参考文献：
  名称：

  级联催化不对称丙二烯的二硼化/烯丙基化/官能化。

  摘要：

  [反应：见正文]钯催化的前手性烯的对映选择性二硼化反应可生成反应性手性烯丙基硼中间体，该中间体是用于羰基烯丙基化的通用试剂。描述了改善该方法的对映选择性，检查底物范围并针对烯丙基化中间体的功能化的实验。

  DOI：

  10.1021/ol052312i

文献信息

• Tetranuclear BINOL−Titanium Complex in Selective Direct Aldol Additions
  作者：Bernd Schetter、Burkhard Ziemer、Gregor Schnakenburg、Rainer Mahrwald

  DOI：10.1021/jo7014054

  日期：2008.2.1

  the direct aldol addition with high degrees of regioselectivity at the sterically more encumbered α-side of unsymmetrical ketones. The formation of quaternary stereocenters is described. Oxygen-containing ene components can also be used as starting material in these reactions. When used with aliphatic aldehydes, acetals 18 or acetals of aldol adducts 20 were observed. As few as 0.2 mol % loadings with

  极其坚固和水稳定的四核配合物的Ti 4（μ-BINOLato）6（μ 3 -OH）4（1）催化的直接醛醇加成与不对称酮的空间更作保α侧高度区域选择性。描述了四元立体中心的形成。在这些反应中，含氧的烯组分也可以用作起始原料。当与脂族醛一起使用时，观察到缩醛18或醛醇加合物20的缩醛。该催化剂1的低至0.2摩尔％的负载量足以完成反应。讨论了反应的机械方面。
• Synthetic applications of titanocene methylene complexes: selective formation of ketone enolates and their reactions
  作者：John R. Stille、Robert H. Grubbs

  DOI：10.1021/ja00344a048

  日期：1983.3
• NOVEL BETA-HYDROXYKETONES AND BETA-ALKOXYKETONES WITH ESTROGENIC ACTIVITY
  申请人：Pulkkinen, Juha

  公开号：EP2227449A1

  公开（公告）日：2010-09-15
• [EN] NOVEL BETA-HYDROXYKETONES AND BETA-ALKOXYKETONES WITH ESTROGENIC ACTIVITY<br/>[FR] NOUVELLES BÊTA-HYDROXYCÉTONES ET BÊTA-ALCOXYCÉTONES PRÉSENTANT UNE ACTIVITÉ OESTROGÉNIQUE
  申请人：PULKKINEN JUHA

  公开号：WO2009066008A1

  公开（公告）日：2009-05-28

  This invention relates to β-hydroxyketones and β-alkoxyketones of formula (I), to their use as estrogen receptor modulators, and to methods for their preparation.
• Concatenated Catalytic Asymmetric Allene Diboration/Allylation/Functionalization
  作者：Angela R. Woodward、Heather E. Burks、Louis M. Chan、James P. Morken

  DOI：10.1021/ol052312i

  日期：2005.11.1

  [reaction: see text] Palladium-catalyzed enantioselective diboration of prochiral allenes generates a reactive chiral allylboron intermediate which is a versatile reagent for the allylation of carbonyls. Experiments that improve the enantioselectivity of this process, examine the substrate scope, and are directed toward functionalization of the allylation intermediate are described.

  [反应：见正文]钯催化的前手性烯的对映选择性二硼化反应可生成反应性手性烯丙基硼中间体，该中间体是用于羰基烯丙基化的通用试剂。描述了改善该方法的对映选择性，检查底物范围并针对烯丙基化中间体的功能化的实验。