1-bromo-4-(3-tosylprop-1-en-2-yl)benzene | 1415643-31-0

• 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-bromo-4-(3-tosylprop-1-en-2-yl)benzene
• 英文别名: 1-[2-(4-Bromophenyl)prop-2-enylsulfonyl]-4-methylbenzene；1-[2-(4-bromophenyl)prop-2-enylsulfonyl]-4-methylbenzene
• CAS: 1415643-31-0
• 化学式: C₁₆H₁₅BrO₂S
• 分子量: 351.264
• InChiKey: RXXBFNJMCWSNRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴苯乙酮 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-bromo-4-(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

• Allylic C–S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation
  作者：Xue Lei、Lei Zheng、Chuanxin Zhang、Xiaodong Shi、Yunfeng Chen

  DOI：10.1021/acs.joc.7b02595

  日期：2018.2.16

  protocol was developed for the preparation of allylic sulfones through direct condensation of sodium arylsulfinates and β,β-disubstituted nitroalkenes. The key step of this process was the Lewis base-promoted equilibrium between nitroalkenes and allylic nitro compounds. Through this process, the readily available conjugated nitroalkenes can be easily converted into allylic nitro compounds, which contain

  开发了一种无金属的开放烧瓶规程，用于通过芳基亚磺酸钠和β，β-二取代的硝基烯烃的直接缩合制备烯丙基砜。该过程的关键步骤是硝基烯烃与烯丙基硝基化合物之间的路易斯碱促进的平衡。通过该方法，容易获得的共轭硝基烯烃可以容易地转化为烯丙基硝基化合物，其对磺酰基自由基加成包含更多的反应性C═C键。结果，在温和条件下以优异的产率制备了烯丙基砜，具有广泛的底物范围。
• 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。