(S)-(-)-p-tolyl vinyl sulfoxide | 27328-17-2

• 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: (S)-(-)-p-tolyl vinyl sulfoxide
• 英文别名: (S)-(p-Me)-phenyl vinyl sulfoxide；(+)-(R)-p-tolyl vinyl sulphoxide；Benzene, 1-[(S)-ethenylsulfinyl]-4-methyl-；1-[(S)-ethenylsulfinyl]-4-methylbenzene
• CAS: 27328-17-2
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: ODAVDFDCUDDZPI-NSHDSACASA-N

物化性质

• 沸点：
  325.4±21.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 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：

  (S)-(-)-p-tolyl vinyl sulfoxide 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (1R,2R,4R)-(+)-oxabicyclo<2.2.1>hept-5-ene-2-p-tolyl sulfide
  参考文献：
  名称：

  Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate

  摘要：

  p-Tolyl vinyl sulfoxide has been efficiently activated for Diels-Alder reactions by transformation into a sulfonium salt 3a or by addition of TMSOTf. Very high diastereomeric excesses have been achieved (> 98%) at -20-degrees-C in many cases. Best results have been obtained with cyclopentadiene, furan and 2,3-dimethyl-1,3-butadiene. In this way enantiomerically pure oxanorbornenone 19a has been prepared. The reaction mechanism is briefly discussed.

  DOI：

  10.1016/s0957-4166(00)82159-x
• 作为产物：
  描述：

  (p-Me)-苯基乙烯基亚砜 在 potassium hydride 、 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (S)-(-)-p-tolyl vinyl sulfoxide
  参考文献：
  名称：

  An efficient resolution of (±)-p-tolylvinylsulfoxide using (−)-menthol

  摘要：

  The preparation of enantiopure (+)-(R)(S) and (-)-(S)(S)-p-tolylvinyisuifoxide using (-)-menthol as a resolving agent is described. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01204-0

文献信息

• Tropane derivatives and method for their synthesis
  申请人：Georgetown University

  公开号：US06350758B1

  公开（公告）日：2002-02-26

  A compound of formula (I) wherein R1-R6 have any of the values defined in the specification are described, as well as pharmaceutical compositions comprising a compound of formula (I), and methods for preparing and using compounds of formula (I) are described.

  公式（I）的化合物，其中R1-R6具有规范中定义的任何值，以及包括公式（I）的化合物的药物组合物，以及描述了制备和使用公式（I）化合物的方法。
• Enantioselective Additive Pummerer-Type Reaction in Chiral, Non-racemic Vinyl Sulfoxides Induced by O-Silylated Ketene Acetal.
  作者：Norio SHIBATA、Chino FUJIMORI、Shigekazu FUJITA、Yasuyuki KITA

  DOI：10.1248/cpb.44.892

  日期：——

  Treatment of chiral, non-racemic vinyl sulfoxides with O-silylated ketene acetal in the presence of a catalytic amount of zinc chloride in tetrahydrofuran resulted in an enantioselective Pummerer-type reaction, affording a considerable yield of the corresponding enantiomerically enriched methyl 4-siloxy-4-sulfenylbutyrate in 78-82% ee.

  在四氢呋喃中催化量的氯化锌存在下，用 O-甲硅烷基化烯酮乙缩醛处理手性非外消旋乙烯基亚砜，产生对映选择性 Pummerer 型反应，得到相当大的产率的相应对映体富集的甲基 4-甲硅烷氧基- 78-82% ee 的 4-硫基丁酸酯。
• Elimination and addition reactions. Part XXVI. Asymmetric induction in additions of nucleophiles and electrophiles to αβ-unsaturated sulphoxides
  作者：Douglas J. Abbott、Stefano Colonna、Charles J. M. Stirling

  DOI：10.1039/p19760000492

  日期：——

  Optically pure αβ-unsaturated sulphoxides have been synthesised.

  已经合成了光学纯的αβ-不饱和亚砜。
• 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.
• Hydrogenative Kinetic Resolution of Vinyl Sulfoxides
  作者：Joan R. Lao、Héctor Fernández-Pérez、Anton Vidal-Ferran

  DOI：10.1021/acs.orglett.5b02139

  日期：2015.8.21

  Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).