1,1-diphenyl-2-(phenylsulfonyl)ethan-1-ol | 59826-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-diphenyl-2-(phenylsulfonyl)ethan-1-ol
• 英文别名: 1,1-Diphenyl-2-(phenylsulfonyl)-1-ethanol；2-(benzenesulfonyl)-1,1-diphenylethanol
• CAS: 59826-93-6
• 化学式: C₂₀H₁₈O₃S
• 分子量: 338.427
• InChiKey: NRGKRBPWASORQY-UHFFFAOYSA-N

物化性质

• 熔点：
  206 °C
• 沸点：
  578.3±50.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯磺酰氯 在 lead 、 1-methoxy-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene 、 tetrabutylammonium tetrafluoroborate 、 水 、 碳酸氢钠 、 甲烷 、 potassium hydrogencarbonate 、 sodium sulfite 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 生成 1,1-diphenyl-2-(phenylsulfonyl)ethan-1-ol
  参考文献：
  名称：

  Electrochemical‐Induced Hydroxysulfonylation of α‐CF ₃ Alkenes to Access Tertiary β‐Hydroxysulfones

  摘要：

  AbstractAn electrochemical hydroxysulfonylation of α‐CF3 alkenes was accomplished in this work. By using easily available sodium sulfinates as the sulfonylating agents, a series of valuable α‐trifluoromethyl tertiary alcohols were synthesized under mild and environmentally friendly electrolysis conditions in moderate to good yields. The preliminary mechanistic investigation indicates that this difunctional reaction involves a radical process via a sulfonyl radical. Gram‐scale synthesis shows the significant potential application of this protocol.magnified image

  DOI：

  10.1002/adsc.202101393

文献信息

• Synthesis and reactivity of the 1,1-dilithio derivatives of alkyl phenyl sulfones and N,N-dimethyl methanesulfonamide
  作者：A. Bongini、D. Savoia、A. Umani-Ronchi

  DOI：10.1016/s0022-328x(00)89360-2

  日期：1976.5

  Alkyl phenyl sulfones Ia,b and N,N-dimethyl methanesulfonamide (Ic) are rapidly converted into their 1,1-dilithio salts IIa–c on reaction with n-butyllithium in THF—hexane. The nature of these new organometallic species was confirmed by deuteration and condensation with benzaldehyde. The gem-dimetallo derivatives Va–c and VIa, obtained from IIa–c by lithium—magnesium and lithium—boron exchange respectively

  与正丁基锂在THF-己烷中反应后，烷基苯基砜Ia，b和N，N-二甲基甲磺酰胺（Ic）迅速转化为1,1-二硫代盐IIa-c。通过氘化和与苯甲醛缩合证实了这些新的有机金属物种的性质。分别通过锂-镁和锂-硼交换从IIa-c获得的宝石双金属衍生物Va-c和VIa与羰基化合物反应生成α，β-不饱和砜VIIa-c和相应的β-羟基砜VIIIa- C。
• Electrochemical synthesis of β-hydroxy-, β-alkoxy-, and β-carbonyloxy sulfones by vicinal difunctionalization of olefins
  作者：Zhefan Zhang、Jiyao Yan、Dengke Ma、Jianwei Sun

  DOI：10.1016/j.cclet.2019.04.023

  日期：2019.8

  Abstract An electrochemical vicinal heterodifunctionalization of olefins for the synthesis of β-oxysulfones is described. With suitable choice of the conditions, including current, electrodes, and electrolyte, this oxidation reaction proceeded efficiently in an undivided cell without the use of a stoichiometric chemical oxidant. In addition to the previously established synthesis of β-hydroxysulfones

  摘要描述了用于合成β-氧砜的烯烃的电化学邻位异二官能化。随着条件的合适选择，包括电流，电极和电解质，该氧化反应在未分开的细胞中有效的进行，而无需使用化学计量的化学氧化剂。除了先前在水存在下建立的β-羟基砜合成以外，通过使用外部醇亲核试剂或内部羧酸亲核试剂对该协议进行的较小修改也导致了β-烷氧基砜和β-磺酰基内酯的合成。
• Multicomponent Sulfonylation of Alkenes to Access β-Substituted Arylsulfones
  作者：Kai-Yi Zhang、Fang Long、Chuan-Chong Peng、Jin-Hui Liu、Yun-Chu Hu、Li-Jun Wu

  DOI：10.1021/acs.joc.2c03036

  日期：2023.3.17

  various β-substituted arylsulfones using cheap and easily available K2S2O5 as a sulfur dioxide source. Of note, the procedure does not need any extra oxidants and metal catalysts and exhibits a relatively wide substrate scope and good functional group compatibility. Mechanistically, an initial arylsulfonyl radical is formed involving the insertion of sulfur dioxide with aryl diazonium salt, followed

  描述了一种新颖的烯烃多组分磺酰化反应，用于使用廉价且易于获得的 K 2 S 2 O 5作为二氧化硫源组装各种 β-取代的芳基砜。值得注意的是，该过程不需要任何额外的氧化剂和金属催化剂，并且具有相对广泛的底物范围和良好的官能团相容性。从机理上讲，初始芳基磺酰基的形成涉及二氧化硫与芳基重氮盐的插入，然后是烯烃的烷氧基芳基磺酰化或羟基磺酰化。
• Photoredox-Catalyzed Radical–Radical Cross-Coupling of Sulfonyl Chlorides with Trifluoroborate Salts
  作者：Sheng-Ping Liu、Yan-Hong He、Zhi Guan

  DOI：10.1021/acs.joc.3c01124

  日期：2023.8.4

  synthesis of sulfone compounds with diverse structures by visible-light-catalyzed radical–radical cross-coupling of sulfonyl chlorides and trifluoroborate salts. Allyl, benzyl, vinyl, and aryl trifluoroborates can be successfully cross-coupled with (hetero)aryl and alkyl sulfonyl chlorides, respectively. This strategy features redox neutrality, good substrate generality, simple operation, and benign reaction

  砜广泛存在于天然产物和药物分子中。在这里，我们公开了一种通过磺酰氯和三氟硼酸盐的可见光催化自由基-自由基交叉偶联直接合成具有不同结构的砜化合物的策略。烯丙基、苄基、乙烯基和芳基三氟硼酸酯可以分别与（杂）芳基和烷基磺酰氯成功交叉偶联。该策略具有氧化还原中性、底物通用性好、操作简单、反应条件良好等特点。
• Visible-Light Induced Radical Addition–Elimination Reaction for Constructing Allylic Sulfones from Sulfonyl Chlorides and Allyl Bromides
  作者：Rui-Xue Li、Yuan Chen、Lan-Qian Huang、Zhi Guan、Yan-Hong He

  DOI：10.1021/acs.joc.3c02893

  日期：2024.4.5

  Allyl sulfones are commonly present in bioactive compounds and organic building blocks. This work introduces a photocatalytic radical addition–elimination reaction involving readily accessible sulfonyl chlorides and allyl bromides. It delivers structurally diverse allylic sulfones in moderate to excellent yields, showcasing a high tolerance to functional groups. Notably, this method operates under

  烯丙基砜通常存在于生物活性化合物和有机结构单元中。这项工作介绍了一种涉及容易获得的磺酰氯和烯丙基溴的光催化自由基加成-消除反应。它以中等至优异的产率提供结构多样的烯丙基砜，表现出对官能团的高度耐受性。值得注意的是，该方法在温和的反应条件下进行，不需要氧化剂、化学计量的还原金属或添加剂。