1-(4-hydroxyphenyl)-3-phenyl-3-(phenylsulfanyl)propan-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-hydroxyphenyl)-3-phenyl-3-(phenylsulfanyl)propan-1-one
• 英文别名: 1-(4-hydroxyphenyl)-3-phenylsulfanyl-3-phenylpropan-1-one；1-(4-hydroxyphenyl)-3-phenyl-3-(phenylthio)propan-1-one；1-(4-Hydroxyphenyl)-3-phenyl-3-phenylsulfanylpropan-1-one
• 化学式: C₂₁H₁₈O₂S
• 分子量: 334.439
• InChiKey: AWOCUQKRCQWGKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(4-hydroxyphenyl)-3-phenyl-3-(phenylsulfanyl)propan-1-one
  参考文献：
  名称：

  Design and synthesis of 1,3-biarylsulfanyl derivatives as new anti-breast cancer agents

  摘要：

  A new series of 1,3-biarylsulfanyl derivatives (homodibenzyl core motif) have been designed and synthesized as new estrogen receptor ligands by chopping benzothiophene core of raloxifene to engender secoraloxifene scaffold. All the synthesized compounds were screened for anti-proliferative, anti-osteoporotic, and anti-implantation activity. Compounds (35, 36) having basic amino anti-estrogenic side chain were exhibiting potential anti-proliferative activity in MCF-7, MDA-MB-231 and ishikawa cell lines. Some of the synthesized compounds having homodibenzyl motif (5, 8, 10) have shown moderate anti-osteoporotic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.056

文献信息

• A mild and highly efficient one-pot three-component reaction for carbon–sulfur bond formation catalyzed by potassium tert-butoxide
  作者：Barahman Movassagh、Amir Rakhshani

  DOI：10.1016/j.cclet.2011.05.015

  日期：2011.7

  Potassium tert-butoxide has been found to be a highly efficient catalyst for one-pot, three-component reaction of aryl aldehydes, acetophenones, and thiols via Claisen–Schmidt/Michael addition reactions for the synthesis of thia-Michael adducts in high yields. The reactions are best carried out in tert-butyl alcohol at room temperature.

  已发现叔丁醇钾是一种高效催化剂，可通过克莱森-施密特/迈克尔加成反应通过一锅，三组分反应芳基醛，苯乙酮和硫醇，从而高产率地合成噻吩-迈克尔加合物。反应最好在室温下在叔丁醇中进行。
• Synthesis of <font>β</font>-Aryl-<font>β</font>-sulfanyl Ketones by a Sequential One-Pot Reaction Using KF/Al₂O₃ in Glycerol
  作者：Gelson Perin、Katiúcia Mesquita、Tainara P. Calheiro、Márcio S. Silva、Eder J. Lenardão、Diego Alves、Raquel G. Jacob

  DOI：10.1080/00397911.2013.788720

  日期：2014.1.2

  The title compounds were synthesized by a sequential one-pot reaction of aryl aldehydes, aryl-methyl ketones, and thiols promoted by KF/Al2O3. This methodology affords a large number of -aryl--sulfanyl ketone derivatives from aliphatic and aromatic thiols in good yields and is also applicable for solid substrates. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Amino acid catalyzed thio-Michael addition reactions
  作者：Atul Kumar、Akanksha

  DOI：10.1016/j.tet.2007.08.033

  日期：2007.11

  Using amino acid as a catalyst, an inexpensive, nontoxic, environmentally friendly, metal-free reaction procedure for C-S bond formation via thio-Michael addition reaction has been developed. The thio-Michael addition products were obtained in excellent yields under mild and neutral conditions. This metal-free catalytic protocol was found to be a good alternative to the existing metal catalyst methodology for the thio-Michael addition reaction. (c) 2007 Elsevier Ltd. All rights reserved.
• Multicomponent, solvent-free synthesis of β-aryl-β-mercapto ketones using zirconium chloride as a catalyst
  作者：Atul Kumar、Akanksha

  DOI：10.1016/j.tetlet.2007.10.023

  日期：2007.12

  Zirconium chloride efficiently catalyzes the one-pot, three-component reaction of an aryl aldehyde, cyclic or acyclic enolizable ketones, and thiols under solvent-free conditions at room temperature to afford the corresponding beta-aryl-beta-mercaptoketones via aldol-Michael addition reactions. This methodology affords a large number of beta-aryl-beta-mercapto ketone derivatives in high yields and in short reaction times. (c) 2007 Elsevier Ltd. All rights reserved.