5-hydroxy-1,6-diphenyl-hexan-3-one | 797762-79-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-hydroxy-1,6-diphenyl-hexan-3-one
• 英文别名: 5-hydroxy-1,6-diphenylhexan-3-one
• CAS: 797762-79-9
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: WWMLUCZLWNRNST-UHFFFAOYSA-N

物化性质

• 沸点：
  439.0±33.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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 、 5-hydroxy-1,6-diphenyl-hexan-3-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25%的产率得到3-(dimethyl-λ4-sulfanylidene)-1,6-diphenyl-hexane-2,4-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：

  5-benzyl-3-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76%的产率得到5-hydroxy-1,6-diphenyl-hexan-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

文献信息

• Synthetic Stitching with Silicon:  Geminal Alkylation−Hydroxylation of Alkynyl Carbonyl Compounds
  作者：Barry M. Trost、Zachary T. Ball

  DOI：10.1021/ja045971j

  日期：2004.11.1

  the synthesis of beta-carbonyl-substituted tertiary alcohols from alpha,beta-alkynyl ketones and esters has been demonstrated. A silicon tether is used to internally deliver an alkyl group, which, combined with a C-Si to C-O transformation, can regio- and diastereoselectively "stitch" together geminal C-C and C-O bonds at the beta-position of an electron-withdrawing group. Regioselective alkyne hydrosilylation

  已经证明了从 α、β-炔基酮和酯合成 β-羰基取代的叔醇的新策略。硅系链用于内部传递烷基，该烷基与 C-Si 到 CO 的转化相结合，可以在吸电子基团的 β 位以区域和非对映选择性“缝合”成对的 CC 和 CO 键。通过反式加成工艺的区域选择性炔烃氢化硅烷化提供了获得三取代乙烯基硅烷的清洁途径。随后的一锅氟化物诱导的 CC 键形成和所得叔硅烷（一种通常对此类条件不具有反应性的硅烷）的氧化提供所需的产物。相邻的酮和羧酸酯基团在促进这些高度受阻叔醇的氧化中的效用，证明了可能会影响取决于此类氧化的路线合成设计的观察结果。对于带有 γ-烷氧基立体中心的底物，观察到良好的非对映选择 (>10:1)。
• Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators
  作者：Enrico Morera、Luciano De Petrocellis、Ludovica Morera、Aniello Schiano Moriello、Marianna Nalli、Vincenzo Di Marzo、Giorgio Ortar

  DOI：10.1016/j.bmcl.2011.12.113

  日期：2012.2

  In order to explore the structural determinants for the TRPV1 and TRPA1 agonist properties of gingerols, a series of nineteen analogues (1b-5) of racemic [6]-gingerol (1a) was synthesized and tested on TRPV1 and TRPA1 channels. The exploration of the structure-activity relationships, by modulating the three pharmacophoric regions of [6]-gingerol, led to the identification of some selective TRPV1 agonists/desensitizers of TRPV1 channels (3a, 3f, and 4) and of some full TRPA1 antagonists (2c, 2d, 3b, and 3d). (C) 2011 Elsevier Ltd. All rights reserved.
• 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.
• 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.