(+)-(R)-2-对甲苯磺酰基-1,3-丁二烯 | 142048-19-9

• 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: (+)-(R)-2-对甲苯磺酰基-1,3-丁二烯
• 英文名称: (+)-(R)-2-p-toluenesulfinyl-1,3-butadiene
• 英文别名: 1-[(R)-buta-1,3-dien-2-ylsulfinyl]-4-methylbenzene
• CAS: 142048-19-9
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: VNGAFWSPONTGAW-CYBMUJFWSA-N

物化性质

• 沸点：
  361.9±21.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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)-2-对甲苯磺酰基-1,3-丁二烯 、 丙炔酸乙酯 以 环己烷 为溶剂， 反应 72.0h， 生成 5-((S)-Toluene-4-sulfinyl)-cyclohexa-1,4-dienecarboxylic acid ethyl ester 、 4-((S)-Toluene-4-sulfinyl)-cyclohexa-1,4-dienecarboxylic acid ethyl ester
  参考文献：
  名称：

  (RS)-4-p-Toluenesulfinylcyclohexa-1,4-dienecarboxylic Acid Ethyl Ester

  摘要：

  The structure determination of C16H18O3S by single-crystal X-ray diffraction revealed the para regiochemistry of the title compound.

  DOI：

  10.1107/s0108270196005744
• 作为产物：
  描述：

  (R)-ethynyl-p-tolyl-sulfoxide 在 双(乙腈)氯化钯(II) 、 N-碘代丁二酰亚胺 、 2,6-二叔丁基-4-甲基苯酚 、 三正丁基氢锡 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (+)-(R)-2-对甲苯磺酰基-1,3-丁二烯
  参考文献：
  名称：

  Synthesis and Diastereoselective Complexation of Enantiopure Sulfinyl Dienes:  The Preparation of Sulfinyl Iron(0) Dienes

  摘要：

  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.

  DOI：

  10.1021/jo970693a

文献信息

• Stereocontrolled synthesis of enantiomerically pure 2-dienyl sulfoxides via palladium-catalyzed coupling reactions
  作者：Robert S. Paley、Heather L. Weers、Paloma Fernández、Roberto Fernández de la Pradilla、Sonia Castro

  DOI：10.1016/0040-4039(95)00604-b

  日期：1995.5

  Enantiopure 2-sulfinyl dienes can be prepared via regio- and stereoselective hydrostannylation of alkynylsulfoxides; after conversion to the corresponding vinyliodides these substrates may be coupled with vinylstannanes via Stille methodology in the presence of BHT.

  对映体纯的2-亚磺酰基二烯可以通过炔基亚砜的区域和立体选择性加氢苯乙烯基化反应来制备。在转化为相应的乙烯基碘之后，可以在BHT存在下通过Stille方法将这些底物与乙烯基锡烷偶联。
• An easy synthesis of chiral sulfinyl allylic bromides and their use in the preparation of(R)S- and (S)S-2-p-tolylsulfinyl-1,3-alkadienes
  作者：Eric Bonfand、Pascal Gosselin、Christian Maignan

  DOI：10.1016/s0957-4166(00)80374-2

  日期：1993.7

  Condensation of (R)-vinyl-p-tolylsulfoxide anion on carbonyl compounds led directly to chiral allylic sulfinylalcohols 1. By treatment with NBS/Me2S, these alcohols 1 were converted into the rearranged primary allylic bromides 2 via SN2' displacement. Optically pure (R)- and (S)-2-p-tolylsulfinyl-1,3-alkadienes 3 resulted from the action of KOH/ROH upon these bromides 2 via E2' eliminations.
• First syntheses of chiral 2-sulfinylbutadienes
  作者：Eric Bonfand、Pascal Gosselin、Christian Maignan

  DOI：10.1016/s0040-4039(00)74207-9

  日期：1992.4

  The title compounds were readily prepared respectively from (S)-3-p-tolylsulfinylbut-3-en-2-ol 3 and (S)-3-p-tolylsulfinylbul-3-en-2-one 4.
• 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.
• (RS)-4-p-Toluenesulfinylcyclohexa-1,4-dienecarboxylic Acid Ethyl Ester
  作者：R. Retoux、J. Molenkamp、E. Bonfand、P. Gosselin、C. Maignan

  DOI：10.1107/s0108270196005744

  日期：1996.9.15

  The structure determination of C16H18O3S by single-crystal X-ray diffraction revealed the para regiochemistry of the title compound.