1-phenyl-3-(phenylsulfonyl)propan-1-one | 65885-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-3-(phenylsulfonyl)propan-1-one
• 英文别名: 3-(benzenesulfonyl)-1-phenylpropan-1-one
• CAS: 65885-28-1
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: IOTOILGYCOMTGK-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  486.1±37.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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-3-(phenylsulfonyl)propan-1-one 在 锂硼氢 作用下， 以80%的产率得到1-phenyl-3-(phenylsulfonyl)-propan-1-ol
  参考文献：
  名称：

  Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes

  摘要：

  Carbanions of 3-substituted-3-chloropropyl phenyl sulfones add to carbonyl groups of aldehydes to produce aldol type adducts that undergo 1,5-intramolecular substitution giving 2,3,5-trisubstituted tetrahydrofurans. The effect of substituents in the 3-position of these sulfones on the relative rates of 1,3-intramolecular substitution of the corresponding gamma-chlorocarbanions and their intramolecular addition are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.006
• 作为产物：
  描述：

  2-Benzenesulfonylmethyl-3-phenyl-oxirane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 1-phenyl-3-(phenylsulfonyl)propan-1-one
  参考文献：
  名称：

  Stereoselective Synthesis of trans-4,5-Disubstituted Oxazolidin-2-ones by Intramolecular Conjugate Addition of N-p-Toluenesulfonyl Carbamates

  摘要：

  DOI：

  10.3987/com-03-9724

文献信息

• Photoredox-Catalyzed Hydroacylation of Olefins Employing Carboxylic Acids and Hydrosilanes
  作者：Muliang Zhang、Rehanguli Ruzi、Junwei Xi、Nan Li、Zhongkai Wu、Weipeng Li、Shouyun Yu、Chengjian Zhu

  DOI：10.1021/acs.orglett.7b01391

  日期：2017.7.7

  hydroacylation reaction of alkenes has been achieved employing readily available carboxylic acids as the acyl source and hydrosilanes as a hydrogen source via photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps has dramatically expanded new applications of carboxylic acids in organic synthesis. The protocol also features extremely mild conditions, broad

  已经通过光氧化还原催化使用容易获得的羧酸作为酰基源和氢硅烷作为氢源实现了烯烃的加氢酰化反应。单电子转移和氢原子转移步骤的结合极大地扩展了羧酸在有机合成中的新应用。该协议还具有极端温和的条件，宽泛的底物范围和良好的官能团耐受性，为烯烃加氢酰化提供了一种新颖而便捷的方法。
• Radical Alkylations of Alkyl Halides and Unactivated C-H Bonds Using Vinyl Triflates
  作者：Sunggak Kim、Jin Lee、Kyoung-Chan Lim、Xiangjian Meng

  DOI：10.1055/s-0029-1219960

  日期：2010.7

  Radical alkylations of activated alkyl iodides and bromides were achieved using vinyl triflates in the presence of hexadimethyltin, whereas those of unactivated C-H bonds using vinyl triflates proceeded cleanly under tin-free conditions.

  在六二甲基锡的存在下，使用乙烯基三氟甲磺酸酯实现了活化的烷基碘和溴化物的自由基烷基化，而使用乙烯基三氟甲磺酸酯的未活化 CH 键的那些在无锡条件下干净地进行。
• Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: applications and mechanism thereof
  作者：Eduardo de Pedro Beato、Daniele Mazzarella、Matteo Balletti、Paolo Melchiorre

  DOI：10.1039/d0sc02313b

  日期：——

  detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue

  我们详细介绍了一种策略，该策略使用相应的氯化物和酸酐通过激活后，使用市售的亲核有机催化剂来生成酰基和氨基甲酰基基团。亲核酰基取代路径。然后，在Giese型加成过程中，所得的亲核基团被各种贫电子烯烃截获。化学过程需要低能光子（蓝色LED）来激活酰基和氨基甲酰基自由基前体，由于它们的高还原电位，因此不容易基于氧化还原的激活机制。为了阐明这种催化光化学自由基产生策略的关键机理，我们结合了瞬态吸收光谱研究，电化学研究，量子产率测量和关键中间体的表征。我们确定了各种非循环中间体，它们与反应性自由基进行光调节平衡。
• A Tin-Free, Radical Photocatalyzed Addition to Vinyl Sulfones
  作者：Davide Ravelli、Sara Montanaro、Michele Zema、Maurizio Fagnoni、Angelo Albini

  DOI：10.1002/adsc.201100591

  日期：2011.12

  Radical conjugate addition onto vinyl sulfones was achieved by means of a convenient, tin-free procedure. This was based on the photocatalyzed CH bond activation in aldehydes, amides, ethers and even cycloalkanes by using tetrabutylammonium decatungstate (TBADT). The reaction was likewise effective for the functionalization of β-substituted vinyl sulfones. The products are useful building blocks and

  通过方便的无锡方法将自由基共轭物加成到乙烯基砜上。这是基于使用四丁基癸酸铵（TBADT）在醛，酰胺，醚甚至环烷烃中的光催化CH键活化。该反应对于β-取代的乙烯基砜的官能化同样有效。该产品是有用的结构单元，在人造紫外线和日光下均能以令人满意的收率获得，因此证明了该工艺的“绿色”潜力。
• Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols
  作者：Yulia A. Konik、Gábor Zoltán Elek、Sandra Kaabel、Ivar Järving、Margus Lopp、Dzmitry G. Kananovich

  DOI：10.1039/c7ob01605k

  日期：——

  ring-opening oxidative sulfonylation to afford γ-keto sulfones when reacting with sulfinate salts in the presence of copper(II) acetate catalyst and an oxidant (tert-butyl hydroperoxide or atmospheric oxygen). Various fluroalkyl, aryl and alkyl sulfinate salts are successfully employed as sulfonylation reagents, affording the corresponding sulfones up to 94% yields. The experimental protocol is mild

  当在乙酸铜（II）催化剂和氧化剂（叔丁基氢过氧化物或大气氧）存在下与亚磺酸盐反应时，叔环丙醇进行开环氧化磺酰化反应，生成γ-酮砜。各种氟烷基，芳基和烷基亚磺酸盐已成功用作磺酰化试剂，相应的砜收率高达94％。实验规程温和，可耐受环丙醇底物中的许多功能。该反应通过一锅氧化-Michael加成反应机理进行，可作为基于Sulfa-Michael反应制备γ-酮砜的现有方法的有用补充。