α-bromovinyl methyl sulfone | 35495-31-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: α-bromovinyl methyl sulfone
• 英文别名: 1-bromo-1-methylsulfonylethylene；1-bromovinylmethyl sulfone；1-bromo-1-methanesulfonyl-ethene；1-Bromo-1-methanesulfonylethene；1-bromo-1-methylsulfonylethene
• CAS: 35495-31-9
• 化学式: C₃H₅BrO₂S
• 分子量: 185.041
• InChiKey: BSTQPTBGKBZMQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  α-bromovinyl methyl sulfone 在 Rieke Zinc 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-methylsulfonyl-ethylene zinc bromide
  参考文献：
  名称：

  WO2006/134459

  摘要：

  公开号：
• 作为产物：
  描述：

  甲基乙烯砜 在 溴 作用下， 生成 α-bromovinyl methyl sulfone
  参考文献：
  名称：

  Bromovinyl sulfone chemistry. Synthesis and rearrangement of the 5-bromo-5-methylsulfonylbicyclo[2.2.1]hept-2-enes

  摘要：

  DOI：

  10.1021/ja00758a060

文献信息

• Substituted arylpyrazoles
  申请人：Billen Denis

  公开号：US20060287365A1

  公开（公告）日：2006-12-21

  This invention relates to a range of 1-aryl-4-cyclopropylpyrazoles in which the cyclopropyl ring is substituted at the angular position, and pharmaceutically acceptable salts and solvates thereof, to compositions comprising such compounds, processes to their synthesis and their use as parasiticides.

  这项发明涉及一系列1-芳基-4-环丙基吡唑，其中环丙基环在角位被取代，以及其药用盐和溶剂合物，包括这些化合物的组合物，它们的合成过程以及它们作为驱虫剂的用途。
• Synthesis of 3,3-diphenyl-3H-pyrazoles applying vinyl sulfones as chemical equivalents of acetylenes in reaction of 1,3-dipolar cycloaddition to diphenyldiazomethane
  作者：V. A. Vasin、V. V. Razin、E. V. Bezrukova、D. Yu. Korovin、P. S. Petrov、N. V. Somov

  DOI：10.1134/s1070428015080138

  日期：2015.8

  α-bromovinyl phenyl sulfones and a-bromovinyl methyl sulfones with diphenyldiazomethane afforded the corresponding 3-bromo- 5,5-diphenyl-3-sulfonyl-Δ1-pyrazolines. The first among them at 20°C suffered spontaneous elimination of molecular nitrogen and converted into 1-bromo-2,2-diphenyl-1-(phenylsulfonyl)cyclopropane whose structure was established by X-ray diffraction analysis. The action of DBU on another

  乙烯基苯基砜，甲基（ë）-3-（苯基磺酰基） -甲基和（ë）-3-（p甲苯磺酰基）丙烯酸酯，（ë）-3-（苯基磺酰基） -和（ë）-3-（p -甲苯磺酰基）丙烯腈在乙醚在20℃下反应与二苯基重氮甲烷，导致相应的5,5-二苯基-3-（芳基磺酰基）的形成- Δ 2 -pyrazolines。在0℃下用DBU在二氯甲烷中用DBU处理时，含有甲氧基羰基或氰基的产物遭受脱氢磺化作用，并转化为4-取代的3，3-二苯基-3 H-吡唑。所提到的Δ的氧化2在20℃下，用活化的二氧化锰在苯中生成吡唑啉，分别形成4-甲氧基羰基-和4-氰基取代的5-芳基磺酰基-3,3-二苯基-3 H-吡唑。α溴乙烯基苯基砜和α-溴乙烯基甲基砜与二苯基重氮甲烷反应，得到相应的3-溴- 5,5-二苯基-3-磺酰-Δ 1 -pyrazolines。它们中的第一个在20°C时会自发消除分子氮，并转化为1-bromo-2,2-二苯基-1-
• An efficient and straightforward route to terminal vinyl sulfones via palladium-catalyzed Suzuki reactions of α-bromo ethenylsulfones
  作者：Yewen Fang、Meijuan Yuan、Juncong Zhang、Li Zhang、Xiaoping Jin、Ruifeng Li、Jinjian Li

  DOI：10.1016/j.tetlet.2016.02.065

  日期：2016.3

  A general and simple protocol for the synthesis of α-substituted alkenylsulfones has been developed firstly via palladium-catalyzed Suzuki reactions between α-bromo ethenylsulfones and organoborons. Using a catalyst composed of Pd(OAc)2 and SPhos, a variety of aryl, heteroaryl, and alkylboron reagents could efficiently couple with α-bromo ethenylsulfones under mild conditions. Moreover, it has been

  首先通过α-溴乙烯基砜与有机硼之间的钯催化的Suzuki反应，开发了一种合成α-取代的链烯基砜的通用且简单的方法。使用由Pd（OAc）2和SPhos组成的催化剂，各种芳基，杂芳基和烷基硼试剂可以在温和的条件下有效地与α-溴乙烯砜偶联。此外，首次证明了乙烯基砜被2-硝基苯磺酰肼的二酰亚胺平滑还原。
• 5-Arylpyrrolidine-2-carboxylic Acid Derivatives as Precursors in the Synthesis of Sulphonyl-substituted Pyrroles
  作者：S. G. Kostryukov、V. A. Kalyazin、P. S. Petrov、E. V. Bezrukova、N. V. Somov

  DOI：10.1134/s1070428024020143

  日期：2024.2

  Abstract cis-5-Arylpyrrolidine-2-carboxylates, obtained by 1,3-dipolar cycloaddition reactions from glycine aryl aldimines and vinyl sulfones, undergo oxidative aromatization under the action of Mn(IV) oxide to form the corresponding 5-arylpyrrole-2-carboxylates in high yields. Factors responsible for the retention of the sulfonyl substituent in the pyrrole backbone were determined.

  摘要 顺式-5-芳基吡咯烷-2-羧酸酯，由甘氨酸芳基醛亚胺和乙烯基砜经1,3-偶极环加成反应得到，在氧化锰(IV)的作用下发生氧化芳构化，生成相应的5-芳基吡咯-2-羧酸酯在高产量中。确定了导致磺酰基取代基保留在吡咯主链中的因素。
• Reaction of 1-bromovinyl and 1-bromo-2-phenylvinyl sulfones with some CH acids
  作者：V. A. Vasin、I. Yu. Bolusheva、V. A. Kalyazin、V. V. Razin

  DOI：10.1134/s1070428014100091

  日期：2014.10

  Benzyl, methyl, and phenyl alpha-bromovinyl sulfones reacted with malononitrile and dimethyl malonate sodium enolates in THF to give sulfonyl-substituted cyclopropanes. Reactions of the same sulfones with methyl acetoacetate sodium enolate afforded the corresponding sulfonyl-substituted cyclopropanes as mixtures of cis and trans isomers with a small impurity of 5-sulfonyl-4,5-dihydrofuran derivative. Phenyl and p-tolyl 1-bromo-2-phenylvinyl sulfones reacted with methyl acetoacetate sodium salt to produce a mixture of trans-isomeric 5-sulfonyl-4,5-dihydrofuran and Michael adduct of the CH acid with activated acetylene generated by concurrent 1,2-dehydrobromination of the initial alpha-bromovinyl sulfone.