ω-bromo-ω-phenylsulfonylacetophenone | 23128-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ω-bromo-ω-phenylsulfonylacetophenone
• 英文别名: α-bromo-α-phenylsulfonylacetophenone；2-bromo-1-phenyl-2-(phenylsulfonyl)ethanone；2-benzenesulfonyl-2-bromo-1-phenyl-ethanone；2-Benzolsulfonyl-2-brom-1-phenyl-aethanon；ω-Brom-ω-phenylsulfon-acetophenon；2-(Benzenesulfonyl)-2-bromo-1-phenylethan-1-one；2-(benzenesulfonyl)-2-bromo-1-phenylethanone
• CAS: 23128-59-8
• 化学式: C₁₄H₁₁BrO₃S
• 分子量: 339.21
• InChiKey: XCTHPMPRRKCKCR-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  478.2±45.0 °C(Predicted)
• 密度：
  1.536±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  ω-bromo-ω-phenylsulfonylacetophenone 在 sodium hydroxide 作用下， 反应 0.5h， 以98%的产率得到溴甲基苯基砜
  参考文献：
  名称：

  Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.11.129
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 双氧水 、 溶剂黄146 作用下， 生成 ω-bromo-ω-phenylsulfonylacetophenone
  参考文献：
  名称：

  Groebel, Chemische Berichte, 1959, vol. 92, p. 2887,2891

  摘要：

  DOI：

文献信息

• Effect of structural change on acute toxicity and antiinflammatory activity in a series of imidazothiazoles and thiazolobenzimidazoles
  作者：Larry J. Powers、S. W. Fogt、Z. S. Ariyan、D. J. Rippin、R. D. Heilman、Richard J. Matthews

  DOI：10.1021/jm00137a022

  日期：1981.5

  The effect of structural change on the biological activity of a series of imidazothiazoles and thiazolobenzimidazoles is described. It was found that compounds with polar substituents at the 2 or 3 position of the ring system are less acutely toxic while maintaining antiinflammatory activity. Other structural changes, such as the incorporation of a gem-dimethyl substituent in the 6 position, increase

  描述了结构变化对一系列咪唑并噻唑和噻唑基苯并咪唑的生物活性的影响。发现在环系统的2或3位具有极性取代基的化合物在维持抗炎活性的同时毒性较小。其他结构变化，例如在6位掺入宝石二甲基取代基，会增加急性毒性并消除抗炎活性。具有最佳活性/毒性比的化合物在噻唑环上包含烷基磺酰基取代基。噻唑并苯并咪唑类似物比咪唑类似物更有效。
• Sodium Telluride-Mediated Sulfenylation of α-Halo Carbonyl Compounds with Diphenyl Disulfide
  作者：Seetharamaiyer Padmanabhan、Takuji Ogawa、Hitomi Suzuki

  DOI：10.1246/bcsj.62.1358

  日期：1989.4.15

  Under mild aprotic conditions α-halo carbonyl compounds react with diphenyl disulfide in the presence of sodium telluride to give the corresponding α-phenylthio derivatives in good to moderate yields. The reaction appears to proceed involving the sulfur–sulfur bond cleavage of diphenyl disulfide by sodium telluride.

  在温和的非质子惰性条件下，α-卤代羰基化合物在碲化钠存在下与二苯基二硫化物反应，以良好到中等的产率得到相应的 α-苯硫基衍生物。该反应似乎涉及碲化钠对二苯基二硫化物的硫-硫键裂解。
• Selenium heterocycles. XLIII. Syntheses of 3,5-Diaryl-1,2,4-thiadiazoles and 3,5-Diaryl-1,2,4-selenadiazoles
  作者：A. Shafiee、M. A. Ebrahimzadeh、A. Maleki

  DOI：10.1002/jhet.5570360412

  日期：1999.7

  tophenones 2 a series of 3,5-diaryl-1,2,4-thiadiazoles and 3,5-diaryl-1,2,4-selenadiazoles were prepared in moderate yield. Reaction of compounds 2 with thiourea or selenourea gave 2-amino-5-arylsulfonyl-4-phenylthiazole or selenazole in good yield.

  从容易获得的α-芳基磺酰基-α-溴苯乙酮2开始，以中等收率制备了一系列3,5-二芳基-1,2,4-噻二唑和3,5-二芳基-1,2,4-硒代二唑。化合物2与硫脲或硒脲的反应以良好的收率得到了2-氨基-5-芳基磺酰基-4-苯基噻唑或硒唑。
• 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%。
• An Efficient Synthesis of Chiral β-Hydroxy Sulfones via Ru-Catalyzed Enantioselective Hydrogenation in the Presence of Iodine
  作者：Xiaobing Wan、Qinghua Meng、Hongwei Zhang、Yanhui Sun、Weizheng Fan、Zhaoguo Zhang

  DOI：10.1021/ol702565x

  日期：2007.12.1

  Ru-SUNPHOS catalyzed asymmetric hydrogenation of a variety of sulfonyl ketones (R = alkyl, aryl) in the presence of iodine gave enantioenriched hydroxyl sulfones with good catalytic efficiency. Further investigation revealed that the in situ generated anhydrous HI is the operating additive.

  Ru-SUNPHOS在碘的存在下催化多种磺酰基酮（R =烷基，芳基）的不对称氢化反应，得到了对映体富集的羟基砜，具有良好的催化效率。进一步的研究表明，原位生成的无水HI是工作添加剂。