(1E,3E)-(+)-(R)-1-(p-tolylsulfinyl)-4-phenyl-1,3-butadiene | 139024-89-8

• 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: (1E,3E)-(+)-(R)-1-(p-tolylsulfinyl)-4-phenyl-1,3-butadiene
• 英文别名: 1-methyl-4-[(R)-[(1E,3E)-4-phenylbuta-1,3-dienyl]sulfinyl]benzene
• CAS: 139024-89-8
• 化学式: C₁₇H₁₆OS
• 分子量: 268.379
• InChiKey: FVQIMJYZMRHXDB-GQEJHBDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (1E,3E)-(+)-(R)-1-(p-tolylsulfinyl)-4-phenyl-1,3-butadiene 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 480.0h， 生成 (+)-(3aR,7aR)-2-Methyl-4-phenyl-3a,7a-dihydroisoindole-1,3-dione
  参考文献：
  名称：

  First Diels-Alder Reactions of Enantiomerically Pure 1-p-Tolylsulfinyl Dienes: Straightforward Access to Cyclohexenols through Tandem Cycloaddition/[2,3]-Sigmatropic Rearrangement

  摘要：

  The asymmetric Diels-Alder reactions of (R)-1-(p-tolylsulfinyl)-1,3-butadienes 3a-c with N-methylmaleimide (NMM) have been explored. The cycloadditions are stereospecific: only one endo adduct is formed, the pi-facial diastereoselectivity being controlled by the sulfoxide both in thermal and catalytic conditions. The in situ cycloaddition/sulfoxide sulfenate [2,3]-sigmatropic rearrange ment starting from chiral 3a-e in the presence of an excess of NMM, which acts as thiophilic agent, provides a convenient one-step access to enantiomerically pure and all-cis functionalized cyclohexenols (-)-5a-c.

  DOI：

  10.1021/jo00091a035
• 作为产物：
  描述：

  (R)-(+)-甲基对甲苯砜 在 sodium hydride 、 lithium diisopropyl amide 、 碘甲烷 作用下， 反应 13.33h， 生成 (1E,3E)-(+)-(R)-1-(p-tolylsulfinyl)-4-phenyl-1,3-butadiene
  参考文献：
  名称：

  Short and Efficient Synthesis of Enantiomerically Pure 4-Substituted (1E,3E)-1[(R)-p-Tolylsulfinyl]-1,3-butadienes

  摘要：

  标题化合物通过 (+)-甲基对甲苯基 (R)-亚磺氧化物与 α,β-不饱和醛的缩合反应，经过一步法脱水得到，易于制备。

  DOI：

  10.1055/s-1991-26633

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.
• Stereoselective Synthesis of Racemic and Optically Active <i>E</i>-Vinyl and <i>E</i>-Dienyl Sulfoxides via Wittig Reaction of α-Sulfinyl Phosphonium Ylides
  作者：Marian Mikołajczyk、Wiesława Perlikowska、Jan Omelańczuk、Henri-Jean Cristau、Anne Perraud-Darcy

  DOI：10.1021/jo981100e

  日期：1998.12.1

  A series of ol-sulfinyl phosphonium ylides have been obtained in the reaction of phosphonium mono- and diylides with sulfinic acid esters. The use of(-)-(S)-menthyl-p-toluenesulfinate in this reaction afforded the corresponding (S)-((p-tolylsulfinyl)methyl)triphenylphosphonium ylide. The Wittig reaction of these ylides with saturated and unsaturated aldehydes resulted in the formation of racemic and optically active (+)-(R)-vinyl and dienyl sulfoxides with the E-geometry. The synthesis of (+)-(R)-((p-tolylsulfinyl)methyl)triphenyl iodide as a precursor of the optically active ylide has also been described.
• Short and Efficient Synthesis of Enantiomerically Pure 4-Substituted (1<i>E</i>,3<i>E</i>)-1[(<i>R</i>)-<i>p</i>-Tolylsulfinyl]-1,3-butadienes
  作者：Guy Solladié、Pilar Ruiz、Françoise Colobert、M. Carmen Carreño、José L. Garcia-Ruano

  DOI：10.1055/s-1991-26633

  日期：——

  The title compounds were readily prepared in two steps by the condensation of (+)-methyl p-tolyl (R)-sulfoxide to α,β-unsaturated aldehydes followed by a one-pot dehydration of the resulting β-hydroxy sulfoxides.

  标题化合物通过 (+)-甲基对甲苯基 (R)-亚磺氧化物与 α,β-不饱和醛的缩合反应，经过一步法脱水得到，易于制备。
• First Diels-Alder Reactions of Enantiomerically Pure 1-p-Tolylsulfinyl Dienes: Straightforward Access to Cyclohexenols through Tandem Cycloaddition/[2,3]-Sigmatropic Rearrangement
  作者：Eva Arce、M. Carmen Carreno、M. Belen Cid、Jose L. Garcia Ruano

  DOI：10.1021/jo00091a035

  日期：1994.6

  The asymmetric Diels-Alder reactions of (R)-1-(p-tolylsulfinyl)-1,3-butadienes 3a-c with N-methylmaleimide (NMM) have been explored. The cycloadditions are stereospecific: only one endo adduct is formed, the pi-facial diastereoselectivity being controlled by the sulfoxide both in thermal and catalytic conditions. The in situ cycloaddition/sulfoxide sulfenate [2,3]-sigmatropic rearrange ment starting from chiral 3a-e in the presence of an excess of NMM, which acts as thiophilic agent, provides a convenient one-step access to enantiomerically pure and all-cis functionalized cyclohexenols (-)-5a-c.