3-(dimethyl-λ4-sulfanylidene)-1,5-diphenyl-pentane-2,4-dione | 161152-04-1

• 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: 3-(dimethyl-λ4-sulfanylidene)-1,5-diphenyl-pentane-2,4-dione
• 英文别名: dimethylsulfonium 1-(phenylacetyl)-2-oxo-3-phenylpropylide；3-(Dimethyl-lambda4-sulfanylidene)-1,5-diphenylpentane-2,4-dione；3-(dimethyl-λ4-sulfanylidene)-1,5-diphenylpentane-2,4-dione
• CAS: 161152-04-1
• 化学式: C₁₉H₂₀O₂S
• 分子量: 312.433
• InChiKey: KOQZVTZXGMARSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(dimethyl-λ4-sulfanylidene)-1,5-diphenyl-pentane-2,4-dione 在 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到1,5-diphenyl-2,4-pentanedione
  参考文献：
  名称：

  制备3-未取代的1,5-二芳基-2,4-戊二酮和-4-甲氧基-2-戊酮的一般方法

  摘要：

  将2-异恶唑啉转化为相应的3-羟基酮，将其用作前体以生产新的3-未取代的1,5-二芳基-2,4-戊二酮和-4-甲氧基-2-戊酮。

  DOI：

  10.1016/0040-4039(94)88376-9
• 作为产物：
  描述：

  苯乙醛肟 在 镍 吡啶 、 sodium hypochlorite 、 N-氯代丁二酰亚胺 、 水 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.5h， 生成 3-(dimethyl-λ4-sulfanylidene)-1,5-diphenyl-pentane-2,4-dione
  参考文献：
  名称：

  3-Unsubstituted 1,5-Diaryl-2,4-pentanediones and -4-methoxy-2-pentanones:  Synthesis via Corresponding 3-Hydroxy Ketones Generated from 2-Isoxazolines

  摘要：

  Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3,5-bis(arylmethyl)-2-isoxazolines which are then converted to 1,5-diaryl-4-hydroxy-2-pentanones by a reductive hydrogenation in the presence of water. These intermediate aldols can then be either oxidized with Corey-Kim reagent to stable dimethylsulfonium 1-(arylacetyl)-2-oxo-3-arylpropylides followed by zinc-acetic acid reduction to give 1,5-diaryl-2,4-pentanediones, or converted to 1,5-diaryl-4-methoxy-2-pentanones by refluxing in methanol in the presence of hydrochloric acid. A detailed study of this general route is reported here.

  DOI：

  10.1021/jo960887a

文献信息

• 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.
• 3-Unsubstituted 1,5-Diaryl-2,4-pentanediones and -4-methoxy-2-pentanones:  Synthesis via Corresponding 3-Hydroxy Ketones Generated from 2-Isoxazolines
  作者：Juha T. Pulkkinen、Jouko J. Vepsäläinen

  DOI：10.1021/jo960887a

  日期：1996.1.1

  Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3,5-bis(arylmethyl)-2-isoxazolines which are then converted to 1,5-diaryl-4-hydroxy-2-pentanones by a reductive hydrogenation in the presence of water. These intermediate aldols can then be either oxidized with Corey-Kim reagent to stable dimethylsulfonium 1-(arylacetyl)-2-oxo-3-arylpropylides followed by zinc-acetic acid reduction to give 1,5-diaryl-2,4-pentanediones, or converted to 1,5-diaryl-4-methoxy-2-pentanones by refluxing in methanol in the presence of hydrochloric acid. A detailed study of this general route is reported here.
• A general route to 3-unsubstituted 1,5-diaryl-2,4-pentanediones and -4-Methoxy-2-pentanones
  作者：Juha Pulkkinen、Jouko Vepsäläinen、Reino Laatikainen

  DOI：10.1016/0040-4039(94)88376-9

  日期：1994.12

  2-Isoxazolines are converted to corresponding 3-hydroxyketones which are used as precursors to produce new 3-unsubstituted 1,5-diaryl-2,4-pentanediones and -4-methoxy-2-pentanones.

  将2-异恶唑啉转化为相应的3-羟基酮，将其用作前体以生产新的3-未取代的1,5-二芳基-2,4-戊二酮和-4-甲氧基-2-戊酮。