1-methoxy-3-(3-tosylprop-1-en-2-yl)benzene | 1415643-28-5

• 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-methoxy-3-(3-tosylprop-1-en-2-yl)benzene
• 英文别名: 1-Methoxy-3-[3-(4-methylphenyl)sulfonylprop-1-en-2-yl]benzene；1-methoxy-3-[3-(4-methylphenyl)sulfonylprop-1-en-2-yl]benzene
• CAS: 1415643-28-5
• 化学式: C₁₇H₁₈O₃S
• 分子量: 302.394
• InChiKey: YQCHRQBTHMXPSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 正丁基锂 、 碘 、 甲基三苯基溴化膦 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 0.33h， 生成 1-methoxy-3-(3-tosylprop-1-en-2-yl)benzene
  参考文献：
  名称：

  Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent

  摘要：

  A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and beta-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.

  DOI：

  10.1021/acs.orglett.7b00896

文献信息

• Efficient synthesis of aliphatic sulfones by Mg mediated coupling reactions of sulfonyl chlorides and aliphatic halides
  作者：Ying Fu、Qin-Shan Xu、Quan-Zhou Li、Zhengyin Du、Ke-Hu Wang、Danfeng Huang、Yulai Hu

  DOI：10.1039/c7ob00251c

  日期：——

  Sulfonyl chlorides were reduced to anhydrous sulfinate salts with magnesium under sonication. These sulfinates were alkylated to sulfones with alkyl chlorides in the presence of catalytic sodium iodide under sonication. A variety of aliphatic sulfones was efficiently prepared by this one-pot two-step procedure.

  在超声处理下，磺酰氯与镁还原为无水亚磺酸盐。在催化的碘化钠存在下，在超声处理下，用烷基氯将这些亚磺酸盐烷基化为砜。通过这一一锅两步程序，可以有效地制备各种脂肪族砜。
• Controllable Activation of β-Alkyl Nitroalkenes: Regioselective Synthesis of Allyl and Vinyl Sulfones
  作者：Ye Wang、Guowei Xiong、Chuanxin Zhang、Yunfeng Chen

  DOI：10.1021/acs.joc.0c02869

  日期：2021.3.5

  hydrazides depended to a great extent on the choice of a solvent and catalyst. In the presence of dimethylformamide (DMF), β-alkyl nitroalkenes more likely converted into electron-rich allyl nitro compounds, which reacted with sulfonyl hydrazides to afford allyl sulfones with high regioselectivity. While in acetonitrile (CH3CN), vinyl sulfones were obtained directly via sulfonation of electron-deficient β-alkyl

  β-烷基硝基烯烃与磺酰肼的区域特异性自由基反应在很大程度上取决于溶剂和催化剂的选择。在二甲基甲酰胺（DMF）的存在下，β-烷基硝基烯烃更可能转化为富含电子的烯丙基硝基化合物，该化合物与磺酰肼反应生成具有高区域选择性的烯丙基砜。在乙腈（CH 3 CN）中时，可通过缺电子的β-烷基硝基烯烃的磺化反应直接获得乙烯基砜。机理研究表明，区域选择性受β-烷基硝基烯烃和烯丙基硝基化合物平衡的控制。
• Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature
  作者：Li Lin、Zhonglie Yang、Jianchen Liu、Jingxia Wang、Jiale Zheng、Jun-Long Li、Xiaobin Zhang、Xiang-Wei Liu、Hezhong Jiang、Jiahong Li

  DOI：10.1039/d1gc00956g

  日期：——

  scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of β-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.

  已经公开了在室温下使用 EDA 复合策略在水中的烯烃的绿色且有效的可见光诱导的碘磺酰基反应。添加阳离子表面活性剂可以在水中轻松形成有色 EDA 复合物。表面活性剂聚集体中的核作为表面活性剂本身在水中形成的反应介质，其疏水作用对稳定过渡态和降低反应活化能起着重要作用。值得注意的是，这种转变不需要过渡金属催化剂和有机溶剂。此外，它具有广泛的底物范围、良好的官能团耐受性、操作简单、可扩展性和高化学选择性。因此，
• Visible-light induced oxidant-free oxidative cross-coupling for constructing allylic sulfones from olefins and sulfinic acids
  作者：Guoting Zhang、Lingling Zhang、Hong Yi、Yi Luo、Xiaotian Qi、Chen-Ho Tung、Li-Zhu Wu、Aiwen Lei

  DOI：10.1039/c6cc04109d

  日期：——

  An oxidant-free dehydrogenative sulfonylation of [small alpha]-methyl-styrene derivatives was developed for the construction of allylic sulfones by using eosin Y as a photosensitizer in conjunction with a cobaloxime catalyst. The process...

  通过使用曙红Y作为光敏剂并结合钴肟肟催化剂，开发了小氧化剂α-甲基-苯乙烯衍生物的无氧化剂脱氢磺酰化，用于构建烯丙基砜。过程...
• Tetrabutylammonium iodide catalyzed allylic sulfonylation of α-methyl styrene derivatives with sulfonylhydrazides
  作者：Xiaoqing Li、Xiangsheng Xu、Can Zhou

  DOI：10.1039/c2cc36960e

  日期：——

  Sulfonyl radicals generated from sulfonylhydrazides by the Bu4NI–tert-butyl hydroperoxide (TBHP) catalysis system underwent addition to a variety of α-methyl styrene derivatives to give the corresponding allylic sulfones. This selective allylic sulfonylation is metal-free, operationally simple, and environmentally friendly.

  通过 Bu4NIâtert-butyl hydroperoxide (TBHP) 催化体系从磺酰肼中生成的磺酰基与多种δ-±-甲基苯乙烯衍生物加成，得到相应的烯丙基砜。这种选择性烯丙基磺酰化反应不含金属，操作简单，对环境友好。