(R)-(E)-2-Bromovinyl p-tolyl sulfoxide | 112373-73-6

• 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: (R)-(E)-2-Bromovinyl p-tolyl sulfoxide
• 英文别名: 1-[(R)-[(E)-2-bromoethenyl]sulfinyl]-4-methylbenzene
• CAS: 112373-73-6
• 化学式: C₉H₉BrOS
• 分子量: 245.14
• InChiKey: CSXZFGYEPRIDLM-NNNHXZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(E)-2-Bromovinyl p-tolyl sulfoxide 在 aluminum amalgam 、 锌铜偶 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-((2R,3R)-5-oxo-2-p-tolylsulfanyl-tetrahydro-furan-3-yl)-malonic acid diethyl ester
  参考文献：
  名称：

  Stereospecific replacement of sulfur from chiral .gamma.-(arylsulfanyl)butyrolactones. Synthesis of optically pure ring-fused .gamma.-butyrolactones

  摘要：

  DOI：

  10.1021/ja00211a047
• 作为产物：
  描述：

  tributyl-[(E)-2-[(R)-(4-methylphenyl)sulfinyl]ethenyl]stannane 以62%的产率得到
  参考文献：
  名称：

  Marino Joseph P., Laborde Edgardo, Deering Carl F., Paley Robert S., Vent+, J. Org. Chem, 59 (1994) N 11, S 3193-3201

  摘要：

  DOI：

文献信息

• Stereocontrolled synthesis of enantiomerically pure dienyl sulfoxides via palladium-catalyzed coupling reactions
  作者：Robert S. Paley、Alfonso de Dios、Roberto Fernández de la Pradilla

  DOI：10.1016/s0040-4039(00)60433-1

  日期：1993.4

  The palladium-catalyzed coupling of enatiopure 2-halovinylsulfoxides and (E)-vinyl stannanes proceeds in an efficient, stereospecific manner to afford enantiopure 1-sulfinyldienes.

  对映体2-卤代戊基亚砜和（E）-乙烯基锡烷的钯催化偶联以有效的立体定向方式进行，得到对映纯的1-亚磺酰基二烯。
• Synthesis and Diastereoselective Complexation of Enantiopure Sulfinyl Dienes:  The Preparation of Sulfinyl Iron(0) Dienes
  作者：Robert S. Paley、Alfonso de Dios、Lara A. Estroff、Jennifer A. Lafontaine、Carlos Montero、David J. McCulley、M. Belén Rubio、Maria Paz Ventura、Heather L. Weers、Roberto Fernández de la Pradilla、Sonia Castro、Rocío Dorado、Miguel Morente

  DOI：10.1021/jo970693a

  日期：1997.9.1

  The preparation of a diverse array of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via Stille coupling of halovinyl sulfoxides and vinyl stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of the corresponding sulfinyl diene iron(0) tricarbonyl complexes was accomplished by utilizing Fe(CO)(5)/NMO or (bda)Fe(CO)(3) as iron(0) tricarbonyl transfer reagents. Installation of the iron(0) tricarbonyl fragment was shown to be highly diastereoselective (10-16:1) for (R)-(1Z)-1-sulfinyl dienes, most likely as a result of allylic 1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene is also described.
• Enantiopure enynyl sulfoxides via palladium-catalyzed coupling reactions
  作者：Robert S. Paley、Jennifer A. Lafontaine、Maria Paz Ventura

  DOI：10.1016/s0040-4039(00)79195-7

  日期：1993.6

  Enantiomerically pure 1-sulfinyl-1-en-3-ynes are prepared from 2-halovinylsulfoxides via Sonogashira or Stille coupling procedures. The trans-enynyl sulfoxides may be hydrogenated to provide (1E, 3Z)-dienylsulfoxides.
• Synthesis of Enantiopure 2-Malonylvinyl Sulfoxides via Addition-Elimination Reactions of 2-Halo- and 2-(Mesyloxy)vinyl Sulfoxides
  作者：Joseph P. Marino、Edgardo Laborde、Carl F. Deering、Robert S. Paley、Maria Paz Ventura

  DOI：10.1021/jo00090a042

  日期：1994.6

  Enantiomerically pure (E)-2-bromo- and (E)-2-iodovinyl sulfoxides 3a and 3b have been prepared in multigram quantities from (E)-1,2-bis(tri-n-butylstannyl)ethene; enantiomerically pure (E)-2-(mesyloxy) vinyl sulfoxide 3c has been synthesized by reaction of the enolate derived from condensation of 1-lithiomethyl p-tolyl sulfoxide and DMF with methanesulfonyl chloride. These compounds react with anions derived from diethyl alkylmalonates to produce enantiopure 2-malonylvinyl sulfoxides in good to excellent yields and with a high degree of stereoselectivity. The transformations proceed through an ''addition-rotation-elimination'' sequence, and the stereochemical results reinforce the concept that nucleophilic additions to vinyl sulfoxides are sterically controlled and occur predominately syn to the sulfinyl electron lone pair.