phenyl isopropenyl sulfoxide | 138689-92-6

• 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: phenyl isopropenyl sulfoxide
• 英文别名: Prop-1-en-2-ylsulfinylbenzene
• CAS: 138689-92-6
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: SBLUOYVXUXTLAA-UHFFFAOYSA-N

物化性质

• 沸点：
  326.5±11.0 °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：

  phenyl isopropenyl sulfoxide 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 (1-Ethoxy-propane-2-sulfonyl)-benzene
  参考文献：
  名称：

  Redman,R.P. et al., Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144

  摘要：

  DOI：
• 作为产物：
  描述：

  isopropenyl phenyl sulfide 在 sodium periodate 作用下， 生成 phenyl isopropenyl sulfoxide
  参考文献：
  名称：

  Reactions of Vinyl Sulfoxides with Magnesium Amides. One-Pot Synthesis of Symmetrical and Unsymmetrical β-(Dialkylamino) Dithioacetals

  摘要：

  Vinyl sulfoxides (PhSOCR1=CHR2: R-1 = H, Me, or Ph; R-2 = H Or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines ((RRNH)-R-3-N-4: R-3 = Et, i-Pr, or Bn; R-4 = Me, Et, or i-Pr) in refluxing Et2O for 1 h, and stirring at room-temperature overnight gave the corresponding symmetrical beta-(dialkylamino) dithioacetals [(PhS)(2)(CRCHRNRR4)-C-1-N-2-R-3] in 24-84% yields. When the (diethylamino)magnesium reagent was treated with appropriate thiols (RSH; R = p-ClC6H4 or Bn) prior to the interaction with phenyl vinyl sulfoxide, the corresponding unsymmetrical beta-(diethylamino) dithioacetals [(PhS)(RS)CHCH2NEt2] were produced in 63-67% yields.

  DOI：

  10.1021/jo970741r

文献信息

• Exploiting Substrate Diversity for Preparing Synthetically Valuable Sulfoxides via Asymmetric Hydrogenative Kinetic Resolution
  作者：Héctor Fernández-Pérez、Joan R. Lao、Arnald Grabulosa、Anton Vidal-Ferran

  DOI：10.1002/ejoc.202000592

  日期：2020.8.2

  The ability of a rhodium catalyst derived from phosphine‐phosphite ligands to hydrogenatively resolve a set of structurally diverse α,β‐unsaturated vinyl sulfoxides is reported. The practicality of the methodology was applied to the preparation of precursors of biologically active compounds.

  据报道，衍生自膦-亚磷酸酯配体的铑催化剂能够氢化分解一组结构多样的α，β-不饱和乙烯基亚砜。该方法的实用性被用于制备生物活性化合物的前体。
• New allene equivalents for the Diels–Alder reaction: vinyl sulphoxide cycloadditions
  作者：Richard Vaughan Williams、Kamlesh Chauhan

  DOI：10.1039/c39910001672

  日期：——

  2-Phenylsulphinylpropene and phenyl vinyl sulphoxide have been shown to be effective allene equivalents for the Diels–Alder reaction.

  已证明2-苯基亚磺酰基丙烯和苯基乙烯基亚砜是狄尔斯-阿尔德反应的有效丙二烯当量。
• Asymmetric approaches to cyclopentenones in the Ni(0)-promoted cyclocarbonylation reaction of allyl halides and acetylenes
  作者：Juan Manuel Villar、Antonio Delgado、Amadeu Llebaria、Josep M. Moretó、Elies Molins、Carles Miravitlles

  DOI：10.1016/0040-4020(96)00573-x

  日期：1996.7

  Different approaches to the asymmetric synthesis of cyclopentenones by means of the Ni(CO)4-promoted alkyne-allyl halide cyclization-carbonylation are reported. The use of acetylenic sulfoxides 1 has proved effective for the synthesis of acyclic, fused [5+8], and spiro [5+5], [5+7], and [5+8] cyclopentenones, whereas placement of the aryl sulfoxide on the allylic system failed to afford any cycloadduct

  报道了通过Ni（CO）4促进的炔-烯丙基卤化物环化-羰基化来不对称合成环戊烯酮的不同方法。乙炔亚砜1的使用已证明对合成无环，稠合[5 + 8]和螺[5 + 5]，[5 + 7]和[5 + 8]环戊烯有效，而芳基亚砜的放置烯丙基体系上的环糊精无法提供任何环加合物。通过这种方法已经获得了手性稠合的[5 + 8]，螺[5 + 7]和[5 + 8]环戊烯酮。最后，当在我们的反应体系中使用不同的同手性α-取代的羧酸盐作为配体时，观察到适度的对映选择性。
• Asymmetric synthesis of (+)-hirsutene
  作者：Duy H. Hua、S. Venkataraman、Robert A. Ostrander、Gurudas Z. Sinai、Peggy J. McCann、M. Jo Coulter、Min Ren Xu

  DOI：10.1021/jo00238a007

  日期：1988.2
• HUA, DUY H.;VENKATARAMAN, S.;OSTRANDER, ROBERT A.;SINAI, GURUDAS-Z.;MCCAN+, J. ORG. CHEM., 53,(1988) N 3, 507-515
  作者：HUA, DUY H.、VENKATARAMAN, S.、OSTRANDER, ROBERT A.、SINAI, GURUDAS-Z.、MCCAN+

  DOI：——

  日期：——