(E)-1,3-双(苯基磺酰基)丙烯 | 32228-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-1,3-双(苯基磺酰基)丙烯
• 英文名称: (E)-(prop-1-ene-1,3-diyldisulfonyl)dibenzene
• 英文别名: (E)-1,3-bis(phenylsulfonyl)propene；E-1,3-bis(phenylsulfonyl)propene；Phenyl-3-phenylsulfonyl-1-propenylsulfon；1,3-Diphenylsulfonylpropen；[(E)-3-(benzenesulfonyl)allyl]sulfonylbenzene；[(E)-3-(benzenesulfonyl)prop-2-enyl]sulfonylbenzene
• CAS: 32228-12-9
• 化学式: C₁₅H₁₄O₄S₂
• 分子量: 322.406
• InChiKey: RSTGVZDDFHPCLL-KPKJPENVSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  582.5±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1,3-双(苯基磺酰基)丙烯 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 20.0~115.0 ℃ 、233.31 Pa 条件下， 反应 10.0h， 生成 1-(苯磺酰基)-4-苯基苯
  参考文献：
  名称：

  Application of Sublimation in the Synthesis and Crystal Growth of Organosulfones

  摘要：

  The solvent‐free elimination of sulfinic acid and aromatization of 1,6‐trans‐substituted bis(arylsulfone) trienes is reported. It is shown that sublimation can be used as a ‘green’ method to combine the thermal transformation of six trienes and the crystal growth of the resulting 4‐(phenylsulfonyl)biphenyls. When the sublimation conditions are carefully controlled, high quality single crystals of the 4‐(phenylsulfonyl)biphenyls are obtained. Theoretical modelling of the reaction using the simplified triene Ph‐(CH)6‐SO2H showed that the cyclization is energetically feasible and that the complete conversion is possible during the timescale of the sublimation. At temperatures slightly higher than the optimum sublimation temperature two of the trienes transformed into 1,4‐cyclohexadienes that did not eliminate phenylsulfinic acid. A reaction mechanism involving a 1,3‐hydrogen shift induced by free PhS. radicals is proposed for the formation of the 1,4‐cyclohexadienes.

  DOI：

  10.1002/chem.202400672
• 作为产物：
  描述：

  2-hydroxy-1,3-bis(phenylthio)propane 在 Oxone 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (E)-1,3-双(苯基磺酰基)丙烯
  参考文献：
  名称：

  Facile Synthesis of Vinyl Sulfones from β-Bromo Alcohols

  摘要：

  Vinyl sulfones are synthesized in good yields by dehydration of beta-hydroxy sulfones derived from beta-bromo alcohols.

  DOI：

  10.1080/00397910008087440

文献信息

• Direct N–H/α,α,β,β-C(sp³)–H functionalization of piperidine<i>via</i>an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles
  作者：Yanlong Du、Aimin Yu、Jiru Jia、Youquan Zhang、Xiangtai Meng

  DOI：10.1039/c6cc08996h

  日期：——

  A protocol for the direct functionalization of N-H/[small alpha],[small alpha],[small beta],[small beta]-C(sp3)-H of piperidine without any metal or external oxidants is reported. These reactions are promoted by 4-(trifluoromethyl)benzoic acid via an azomethine ylide intermediate....

  报道了在没有任何金属或外部氧化剂的情况下将哌啶的NH /小α，小α，小β，小β-C（sp 3）-H直接官能化的方案。这些反应是由4-（三氟甲基）苯甲酸通过甲亚胺叶立德中间体促进的。
• Regioselective Synthesis of Substituted Arenes via Aerobic Oxidative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and Ketones
  作者：Prabhakar Ramchandra Joshi、Sridhar Undeela、Doni Dhanoj Reddy、Kiran Kumar Singarapu、Rajeev S. Menon

  DOI：10.1021/acs.orglett.5b00318

  日期：2015.3.20

  Facile conversion of α,β-unsaturated aldehydes and ketones into highly substituted arenes via a base-mediated, completely regioselective, air-oxidative [3 + 3] benzannulation reaction with readily available 4-sulfonylcrotonates or 1,3-bisphenylsulfonylpropene is reported. The reaction can also be carried out as a one-pot, three-component operation using 4-bromocrotonates, aryl sulfinates, and cinnamaldehyde

  据报道，α，β-不饱和醛和酮可以通过碱介导的，完全区域选择性的，空气氧化的[3 + 3]苯并环乙烷反应与容易获得的4-磺酰基巴豆酸酯或1,3-双苯基磺酰基丙烯轻松地转化为高度取代的芳烃。该反应还可以使用4-溴巴豆酸酯，芳基亚磺酸酯和肉桂醛作为一锅三组分操作进行。这种开瓶，无金属的反应不需要无水溶剂，可以在温和的条件下进行，并使用大气中的氧气作为氧化剂，可提供高产率的3-（芳基磺酰基）苯甲酸酯。
• A practical synthesis of functionalized isoindolinones via [3 + 3] benzannulation of 1,3-bissulfonylpropenes and 4-arylmethylene-2,3-dioxopyrrolidines
  作者：Xiang-zheng Tang、Jing-xuan zhou、Hua-ju Liang、Xue-jing Zhang、Ming Yan、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2018.11.074

  日期：2019.1

  straightforward synthesis of isoindolinones has been developed via a [3 + 3] benzannulation of 4-arylmethylene-2,3-dioxopyrrolidines and 1,3-bissulfonylpropenes (or 4-sulfonylcrotonates). A series of functionalized isoindolinones were obtained in excellent yields. The reaction could be carried out under mild conditions without transition metal catalyst. The finding provides a practical approach for the

  通过4-芳基亚甲基-2,3-二氧吡咯烷和1,3-双磺酰基丙烯（或4-磺酰基巴豆酸酯）的[3 + 3]苯环已开发出异吲哚啉酮的直接合成方法。以优异的产率获得了一系列官能化的异吲哚啉酮。该反应可以在温和的条件下进行而无需过渡金属催化剂。该发现为制备具有潜在生物学活性的异吲哚啉酮衍生物提供了一种实用的方法。
• Facile synthesis of substituted diaryl sulfones <i>via</i> a [3 + 3] benzannulation strategy
  作者：Xiang-zheng Tang、Lang Tong、Hua-ju Liang、Jie Liang、Yong Zou、Xue-jing Zhang、Ming Yan、Albert S. C. Chan

  DOI：10.1039/c8ob00662h

  日期：——

  base-mediated [3 + 3] benzannulation strategy for the conversion of 1,3-bis(sulfonyl)propenes and β,γ-unsaturated α-ketoesters to diaryl sulfones has been developed. This method provides facile, metal-free and efficient access to highly substituted diaryl sulfones in good to excellent yields. In addition, the sulfonyl group could be easily removed or converted to other functional groups via an organostannane

  已开发出一种由碱介导的[3 + 3]苯环芳构化策略，可将1,3-双（磺酰基）丙烯和β，γ-不饱和α-酮酸酯转化为二芳基砜。该方法可以轻松，无金属且高效地获得高取代的二芳基砜，且收率良好。另外，磺酰基可通过有机锡烷中间体容易地除去或转化为其他官能团。
• An Original Synthesis of Allyl Sulfones and (Trimethylsilyl)-vinyl Sulfones
  作者：J. -P. PILLOT、J. DUNOGUÈS、R. CALAS

  DOI：10.1055/s-1977-24447

  日期：——