3-(4-Chlorophenyl)-1-phenyl-3-(phenylsulfonyl)propan-1-one | 301305-91-9

• 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: 3-(4-Chlorophenyl)-1-phenyl-3-(phenylsulfonyl)propan-1-one
• 英文别名: 3-(benzenesulfonyl)-3-(4-chlorophenyl)-1-phenylpropan-1-one
• CAS: 301305-91-9
• 化学式: C₂₁H₁₇ClO₃S
• 分子量: 384.883
• InChiKey: LRXXVPOEWJTDEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  595.1±50.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 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：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-Chlorophenyl)-1-phenyl-3-(phenylsulfonyl)propan-1-one 在 potassium fluoride 、 C₄₆H₅₀I₄O₆ 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以40%的产率得到(R)-3-(4-chlorophenyl)-1-phenyl-3-(phenylsulfonyl)propan-1-one
  参考文献：
  名称：

  阳离子结合聚醚催化剂通过对映选择性消除β-磺酰基酮的动力学拆分

  摘要：

  本文报道的是手性阳离子结合聚醚催化的第一个对映选择性β-消除反应。通过使用这种催化方案，可以以高的立体选择性（S高达> 300）有效地分离各种β-磺酰基酮。该方法成功的关键是催化剂与砜基质上的路易斯碱性基团之间有利的二次相互作用。该方法的烯酮产物可轻松转化为外消旋原料，并可以高收率和出色的对映选择性有效地循环利用和全面合成手性β-磺酰基酮。

  DOI：

  10.1002/anie.201508127
• 作为产物：
  描述：

  1-phenyl-3-(4-chlorophenyl)-3-phenylsulfenylpropan-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到3-(4-Chlorophenyl)-1-phenyl-3-(phenylsulfonyl)propan-1-one
  参考文献：
  名称：

  Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones

  摘要：

  Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 degrees C in a novel method. Both sulfones and bisulfones were evaluated for their antimicrobial activities against Aspergillus niger and Candida albicans (yeast), Bacillus subtilis and Staphylococcus aureus (Gram (+) bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram (-) bacteria) strains. Among them, compounds 2c, 3c, 6c, 7c, 8c and 9c have shown high antifungal activity against C albicans compare to reference drugs viz. Amphotericin-B and Nystatin. Compound 1c has shown slightly better antibacterial activity against B. subtilis and compounds 5c, 6c and 7c have shown excellent antibacterial activity against S. typhimurium in compare to reference drugs Ampicillin and Kanamycin. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.004

文献信息

• Enantioselective Sulfonation of Enones with Sulfinates by Thiourea/Tertiary-Amine Catalysis
  作者：Guang-xun Li、Jin-zhong Zhao、Si-fan Wang、Ming Yan、Jin-yi Shi

  DOI：10.1055/a-2202-0842

  日期：——

  substrates that could be converted into sulfinic acids by treatment with boric acid. The bifunctional catalyst forms a chiral ion pair with the sulfinic acid and controls the enantioselectivity of the sulfonation through hydrogen bonding.

  手性γ-酮砜是有机合成和药物化学中的重要结构。尽管获得外消旋形式有多种选择，但仅报道了少数对映选择性方法。我们开发了一种简单的方法，可以以中等产率和中等对映体比例获得手性 γ-酮砜。直接使用现成的亚磺酸盐作为底物，通过硼酸处理可以将其转化为亚磺酸。双功能催化剂与亚磺酸形成手性离子对，并通过氢键控制磺化的对映选择性。
• Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones
  作者：Naveen Kumar Konduru、Sunita Dey、Mohammad Sajid、Mohammad Owais、Naseem Ahmed

  DOI：10.1016/j.ejmech.2012.09.004

  日期：2013.1

  Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 degrees C in a novel method. Both sulfones and bisulfones were evaluated for their antimicrobial activities against Aspergillus niger and Candida albicans (yeast), Bacillus subtilis and Staphylococcus aureus (Gram (+) bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram (-) bacteria) strains. Among them, compounds 2c, 3c, 6c, 7c, 8c and 9c have shown high antifungal activity against C albicans compare to reference drugs viz. Amphotericin-B and Nystatin. Compound 1c has shown slightly better antibacterial activity against B. subtilis and compounds 5c, 6c and 7c have shown excellent antibacterial activity against S. typhimurium in compare to reference drugs Ampicillin and Kanamycin. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst
  作者：Liang Li、Yidong Liu、Yang Peng、Lei Yu、Xiaoyan Wu、Hailong Yan

  DOI：10.1002/anie.201508127

  日期：2016.1.4

  Reported herein is the first enantioselective β‐elimination reaction catalyzed by a chiral cation‐binding polyether. By using this catalytic protocol, a wide range of β‐sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate

  本文报道的是手性阳离子结合聚醚催化的第一个对映选择性β-消除反应。通过使用这种催化方案，可以以高的立体选择性（S高达> 300）有效地分离各种β-磺酰基酮。该方法成功的关键是催化剂与砜基质上的路易斯碱性基团之间有利的二次相互作用。该方法的烯酮产物可轻松转化为外消旋原料，并可以高收率和出色的对映选择性有效地循环利用和全面合成手性β-磺酰基酮。