phenyl 2,2-diphenylethenyl sulfone | 26189-62-8

• 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: phenyl 2,2-diphenylethenyl sulfone
• 英文别名: (2-(phenylsulfonyl)ethene-1,1-diyl)dibenzene；[1-Phenyl-2-(phenylsulfonyl)vinyl]benzene；[2-(benzenesulfonyl)-1-phenylethenyl]benzene
• CAS: 26189-62-8
• 化学式: C₂₀H₁₆O₂S
• 分子量: 320.412
• InChiKey: JGHGEBHNSZDBKF-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  507.3±50.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl 2,2-diphenylethenyl sulfone 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 3,3-diphenyl-2-(phenylsulfonyl)-2-propenyl chloroformate
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d
• 作为产物：
  描述：

  2-benzenesulfinyl-1,1-diphenylethanol 在 磺酰氯 作用下， 生成 phenyl 2,2-diphenylethenyl sulfone
  参考文献：
  名称：

  Neighboring Group Participation in the Halogenation of Sulfoxides

  摘要：

  PhS(O)(CH₂)ₙCH₂OH(n = 1–3) 在氯化亚砜氯在−78°或0°的氯化亚砜中反应，得到相应的PhSO₂(CH₂)ₙCH₂Cl。有证据表明，环状烷氧氧代磺鎓盐是这些转化中间体。当n = 4时，只观察到对亚砜功能的α氯化。烷磺酰基羧酸PhS(O)(CH₂)ₙCO₂H (n = 1–3) 和酰胺PhS(O)(CH₂)ₙCONH₂ (n = 1–3) 也与SO₂Cl₂反应。当n = 1或3时，两种化合物均观察到α氯化。当n = 2时，产物分别为3-苯基磺酰基丙酰氯和3-苯基磺酰基丙腈。

  DOI：

  10.1139/v73-256

文献信息

• Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides
  作者：Yu-Jing Guo、Shuai Lu、Lu-Lu Tian、En-Ling Huang、Xin-Qi Hao、Xinju Zhu、Tian Shao、Mao-Ping Song

  DOI：10.1021/acs.joc.7b02734

  日期：2018.1.5

  Novel iodine-induced sulfonylation and sulfenylation of imidazopyridines have been described using sodium sulfinates as the sulfur source. This strategy enables highly selective difunctionalization of imidazo[1,2-a]pyridine to access sulfones and sulfides in good yields. A wide range of substrates and functional groups were well-tolerated under optimized conditions. Moreover, control experiments have

  已经描述了使用亚磺酸钠作为硫源的新的碘诱导的咪唑并吡啶的磺酰化和亚磺酰化。该策略能够使咪唑并[1,2- a ]吡啶高度选择性地进行双官能化，从而以高收率获得砜和硫化物。在最佳条件下，各种底物和官能团均具有良好的耐受性。此外，已经进行了对照实验，表明了反应机理中涉及的自由基途径。
• Nickel-Catalyzed Sulfonylation of C(<i>sp</i>²)-H Bonds with Sodium Sulfinates
  作者：Shuang-Liang Liu、Xue-Hong Li、Shu-Sheng Zhang、Sheng-Kai Hou、Guang-Chao Yang、Jun-Fang Gong、Mao-Ping Song

  DOI：10.1002/adsc.201700290

  日期：2017.7.3

  substrate scope and good functional group tolerance with high monosulfonylation selectivity. Besides arenes and heteroarenes, the reaction can also be extended to alkenes, providing diverse diaryl and alkyl aryl sulfones in high yields. Furthermore, a plausible Ni(I)/Ni(III) mechanism is outlined based on our experimental results and related precedents.

  描述了由（吡啶-2-基）异丙胺（PIP-胺）引导的亚磺酸钠对C（sp 2）-H键的首次镍催化邻位磺酰化反应。该策略展示了宽的底物范围和良好的官能团耐受性以及高的单磺酰化选择性。除了芳烃和杂芳烃之外，该反应还可以扩展至烯烃，以高收率提供各种二芳基和烷基芳基砜。此外，根据我们的实验结果和相关先例，概述了可能的Ni（I）/ Ni（III）机制。
• Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis
  作者：Kaining Zhang、Liang Chang、Qing An、Xin Wang、Zhiwei Zuo

  DOI：10.1021/jacs.9b05932

  日期：2019.7.3

  functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional

  脱羟甲基化是将醇原料直接转化为少一个碳原子的烷基合成子，是一种利用醇材料的普遍性和稳健性的非常规且未充分探索的策略。在温和且氧化还原中性的反应条件下，利用廉价的铈催化剂，提供了光催化脱羟甲基化平台。通过配体到金属的电荷转移催化，醇官能团已可靠地转移到亲核自由基中，同时失去一分子甲醛。有趣的是，我们发现铈催化剂可以显着促进脱羟甲基化过程，并且碎片自由基的稳定作用也起着重要作用。这种操作简单的方案能够直接利用伯醇作为非常规烷基亲核试剂，用于自由基介导的 1,4-共轭加成与迈克尔受体。广泛的醇类，从简单的乙醇到复杂的核苷和类固醇，已成功应用于这种片段偶联转化。此外，该催化系统的模块化已在多种自由基介导的转化中得到证实，包括氢化、胺化、烯基化和氧化。
• Electrosynthesis of (<i>E</i>)-Vinyl Sulfones Directly from Cinnamic Acids and Sodium Sulfinates via Decarboxylative Sulfono Functionalization
  作者：Peng Qian、Meixiang Bi、Jihu Su、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.joc.6b00661

  日期：2016.6.3

  A variety of (E)-vinyl sulfones were constructed directly from cinnamic acids and sodium sulfinates with high regioselectivity at room temperature by virtue of an electrocatalytic oxidation. A radical intermediate was detected, and the corresponding mechanism was investigated.

  借助于电催化氧化，在室温下由肉桂酸和亚磺酸钠直接以高区域选择性直接构建了多种（E）-乙烯基砜。检测到自由基中间体，并研究了相应的机理。
• Palladium-Catalyzed Cascade Reaction of α,β-Unsaturated Sulfones with Aryl Iodides
  作者：Pablo Mauleón、Angel A. Núñez、Inés Alonso、Juan C. Carretero

  DOI：10.1002/chem.200390173

  日期：2003.4.4

  Unlike traditionally used acyclic 1,2-disubstituted alkenes, the reaction of alpha,beta-unsaturated phenyl sulfones with aryl iodides under Heck reaction conditions (Pd(OAc)(2) as catalyst, Ag(2)CO(3) as base in DMF at 120 (0)C) takes place mainly by a cascade process, involving one unit of the alkene and three units of the aryl iodide, to afford a substituted 9-phenylsulfonyl-9,10-dihydrophenanthrene

  与传统上使用的无环1,2-二取代烯烃不同，α，β-不饱和苯基砜与芳基碘化物在Heck反应条件下反应（以Pd（OAc）（2）为催化剂，Ag（2）CO（3）为碱在120（0）℃下的DMF主要通过级联过程进行，包括一个单元的烯烃和三个单元的芳基碘，以提供取代的9-苯基磺酰基-9,10-二氢菲。这种3：1偶联产物而不是Heck三取代烯烃的主要结构表明，芳族CH键的活化过程可以与无环烯烃的Heck芳基化反应中通常快速的合成β-氢消除步骤竞争。已证明，钯催化的α，β-不饱和砜的级联芳基化的结构范围很广，涉及到β-位置（烷基，芳基，或烯基取代基），砜单元上的取代基（烷基或苯基砜）和CdoublebondC键上的构型（反式或顺式）。此外，尽管不如在α，β-不饱和砜芳基化的情况下受到青睐，但是在α，β-不饱和膦氧化物和α，β-不饱和膦酸酯的情况下也获得了类似取代的9，10-二氢菲。 。提出了一种Pd（0）-