2-氯-1-苯基-2-(苯基磺酰基)乙酮 | 38009-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-1-苯基-2-(苯基磺酰基)乙酮
• 英文名称: 2-chloro-1-phenyl-2-(phenylsulfonyl)ethanone
• 英文别名: 2-benzenesulfonyl-2-chloro-1-phenylethanone；(α-Chlormethylbenzoyl)phenylsulfon；ω-Chlor-ω-phenylsulfon-acetophenon；2-Benzolsulfonyl-2-chlor-1-phenyl-aethanon；2-(Benzenesulfonyl)-2-chloro-1-phenylethan-1-one；2-(benzenesulfonyl)-2-chloro-1-phenylethanone
• CAS: 38009-92-6
• 化学式: C₁₄H₁₁ClO₃S
• mdl: MFCD28505996
• 分子量: 294.759
• InChiKey: SIHHNFVNKICLHI-UHFFFAOYSA-N

物化性质

• 沸点：
  479.7±45.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 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：

  2-氯-1-苯基-2-(苯基磺酰基)乙酮 在 sodium hydroxide 作用下， 反应 0.5h， 以98%的产率得到氯甲基苯砜
  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：

  2-(苯基磺酰基)重氮苯乙酮 在 copper(II) bis(trifluoromethanesulfonate) 、 氯化铵 作用下， 以 硝基甲烷 为溶剂， 反应 20.0h， 以74%的产率得到2-氯-1-苯基-2-(苯基磺酰基)乙酮
  参考文献：
  名称：

  三氟甲磺酸铜与卤化铵介导的α-重氮β-酮砜的α-单卤代反应

  摘要：

  摘要 三氟甲磺酸铜介导的α-重氮β-酮砜与卤化铵的α-单卤化作用提供了相应的α-卤代β-酮砜。为了实现这种便捷而有效的转换，研究了不同的金属三氟甲磺酸盐。提出了一个合理的机制。 三氟甲磺酸铜介导的α-重氮β-酮砜与卤化铵的α-单卤化作用提供了相应的α-卤代β-酮砜。为了实现这种便捷而有效的转换，研究了不同的金属三氟甲磺酸盐。提出了一个合理的机制。

  DOI：

  10.1055/s-0036-1589479

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。
• Synthesis of α-halogeno-sulphoxides
  作者：M. Cinquini、S. Colonna

  DOI：10.1039/p19720001883

  日期：——

  Reaction of sulphoxides with (dichloroiodo)benzene or with bromine in the presence of pyridine affords the corresponding α-halogeno-sulphoxides. Some reactions of α-halogeno-sulphoxides are here described.

  亚砜与（二氯碘代）苯或与溴在吡啶存在下反应，得到相应的α-卤代亚砜。这里描述了α-卤代亚砜的一些反应。
• 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。
• Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products
  作者：Xiaobo Xu、Leyu Yan、Zhi-Kai Zhang、Bingqing Lu、Zhuangwen Guo、Mengyue Chen、Zhong-Yan Cao

  DOI：10.3390/molecules27154675

  日期：——

  A practical method for the deoxygenation of α-hydroxyl carbonyl compounds under mild reaction conditions is reported here. The use of cheap and easy-to-handle Na2S·9H2O as the reductant in the presence of PPh3 and N-chlorosuccinimide (NCS) enables the selective dehydroxylation of α-hydroxyl carbonyl compounds, including ketones, esters, amides, imides and nitrile groups. The synthetic utility is demonstrated

  本文报道了一种在温和反应条件下使 α-羟基羰基化合物脱氧的实用方法。在 PPh 3和N-氯代琥珀酰亚胺 (NCS) 存在下，使用廉价且易于处理的 Na 2 S·9H 2 O 作为还原剂，可以对 α-羟基羰基化合物（包括酮、酯、酰胺）进行选择性脱羟基、酰亚胺和腈基团。合成效用通过生物活性分子和复杂天然产物的后期脱氧来证明。
• Synthesis of Fluorinated β-Ketosulfones and <i>gem</i>-Disulfones by Nucleophilic Fluoroalkylation of Esters and Sulfinates with Di- and Monofluoromethyl Sulfones
  作者：Chuanfa Ni、Laijun Zhang、Jinbo Hu

  DOI：10.1021/jo900320b

  日期：2009.5.15

  An efficient and practically useful method for the preparation of alpha-functionalized mono- and difluoro(phenylsulfonyl)methanes by using a nucleophilic fluoroalkylation methodology was developed. alpha,alpha-Difluoro-P-ketosulfones, alpha-monofluoro-beta-ketosulfones, and alpha-fluoro disulfones were successfully prepared in excellent yields by nucleophilic fluoroalkylation of esters and sulfinates with PhSO2CF2H and PhSO2CH2F reagents.