1-phenyl-2-(phenylsulfonyl)butan-1-one | 131454-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2-(phenylsulfonyl)butan-1-one
• 英文别名: 2-(Benzenesulfonyl)-1-phenylbutan-1-one
• CAS: 131454-22-3
• 化学式: C₁₆H₁₆O₃S
• 分子量: 288.367
• InChiKey: MMCPZEUWAVKXST-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  480.9±37.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(phenylsulfonyl)butan-1-one 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以74%的产率得到苯丁酮
  参考文献：
  名称：

  Reductive Desulfonylation of β-Ketosulfones by TiCl4–Zn†

  摘要：

  β-酮砜类化合物在温和条件下可以通过TiCl4-Zn体系容易地还原，得到相应的高收率酮类化合物。

  DOI：

  10.1039/a606405a
• 作为产物：
  描述：

  sodium benzenesulfonate 在 苄基三乙基溴化铵 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 1-phenyl-2-(phenylsulfonyl)butan-1-one
  参考文献：
  名称：

  Grossert, J. Stuart; Dharmaratne, H. Ranjith W.; Cameron, T. Stanley, Canadian Journal of Chemistry, 1988, vol. 66, p. 2860 - 2869

  摘要：

  DOI：

文献信息

• Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis
  作者：Jun Xu、Chao Shen、Xian Qin、Jie Wu、Pengfei Zhang、Xiaogang Liu

  DOI：10.1021/acs.joc.0c02249

  日期：2021.3.5

  A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.

  证明了铜/银共催化的sulf的氧化磺酰化方案。可以以中等到良好的产率直接合成各种各样的β-酮砜和N-酰基磺酰胺。我们的工作为在制药工业中发现了广泛应用的β-酮砜衍生物的可扩展制备提供了一种可行的方法。
• A Convenient Method for Reductive Desulfonylation of β-Ketosulfones with Sm/HgCl₂System
  作者：Hongyun Guo、Yongmin Zhang

  DOI：10.1080/00397910008087420

  日期：2000.7

  Abstract The Sm/HgCl2 system reduces β-ketosulfones to the corresponding ketones in moderate to good yield under mild conditions.

  摘要 Sm/HgCl2 系统在温和条件下以中等至良好的收率将 β-酮砜还原为相应的酮。
• Dynamic kinetic resolution of β-keto sulfonesvia asymmetric transfer hydrogenation
  作者：Zhenhua Ding、Jin Yang、Ting Wang、Zongxuan Shen、Yawen Zhang

  DOI：10.1039/b818257d

  日期：——

  The dynamic kinetic resolution of β-keto sulfones was achieved via asymmetric transfer hydrogenation using (S,S)-RuCl[N-(tosyl)-1,2-diphenylethylenediamine](p-cymene) in the presence of formic acid and triethylamine afforded the desired products in good yield with up to >99 : 1 dr and high ee up to >99%.

  在甲酸和三乙胺存在下，使用(S,S)-RuCl[N-(甲苯基)-1,2-二苯基乙二胺](对-氰基)通过不对称转移加氢实现了δ-酮砜的动态动力学解析，得到了所需产物，收率高达 >99 : 1 dr，ee高达 >99%。
• Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones
  作者：N. Suryakiran、P. Prabhakar、T. Srikanth Reddy、K. Chinni Mahesh、K. Rajesh、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2006.11.129

  日期：2007.1

  The synthesis of alpha-halo beta-keto-sulfones using potassium halide and hydrogen peroxide as a chemoselective mono halogenation reagent and the synthesis of alpha, alpha-symmetrical and asymmetrical dihalo beta-keto-sulfones and alpha-halo, alpha-alkyl and beta-keto-sulfones is described. Base induced cleavage of alpha-halo beta-keto-sulfones, alpha,alpha-dihalo beta-keto-sulfones, and alpha-halo, alpha-alkyl beta-keto-sulfones afforded the corresponding halomethyl sulfones, dihalomethyl sulfones and haloalkyl sulfones. (c) 2006 Elsevier Ltd. All rights reserved.
• Efficient Diastereoselective Syntheses of <i>erythro</i>- or <i>threo</i>-α-Alkyl-β-hydroxy Sulfones by Reductions of α-Alkyl-β-keto Sulfones with TiCl₄/BH₃ or LiEt₃BH/CeCl₃, Respectively
  作者：Enrico Marcantoni、Simone Cingolani、Giuseppe Bartoli,*、Marcella Bosco、Letizia Sambri

  DOI：10.1021/jo972284k

  日期：1998.5.1

  A stereoselective synthesis of erythro- and threo-alpha-alkyl-beta-hydroxy sulfones by reduction of the corresponding alpha-alkyl-beta-keto sulfones has I,een developed. The pivotal role in this methodology is played by the chelating or nonchelating properties of the Lewis acid employed. The strong chelating TiCl4 led to the erythro isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 degrees C using BH3/py as reducing agent, while the nonchelating CeCl3 gave a high excess of the three isomer in coordinating solvents (THF) at the same temperature using lithium triethylborohydride (LiEt3BH) as reducing agent. Moreover, this methodology has been successfully utilized for the synthesis of alpha-allyl-beta-hydroxy sulfones, which are useful synthetic intermediates to obtain 2,5-disubstituted tetrahydrofurans by electrophilic cyclization.