(+/-)-(Z)-5-phenyl-4-(p-tolylsulfenyl)pent-4-en-3-ol | 479623-83-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (+/-)-(Z)-5-phenyl-4-(p-tolylsulfenyl)pent-4-en-3-ol
• 英文别名: (Z)-2-(4-methylphenyl)sulfanyl-1-phenylpent-1-en-3-ol
• CAS: 479623-83-1
• 化学式: C₁₈H₂₀OS
• 分子量: 284.422
• InChiKey: BESNSEIVWPWUSH-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(Z)-5-phenyl-4-(p-tolylsulfenyl)pent-4-en-3-ol 在 叔丁基过氧化氢 、 正丁基锂 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 13.17h， 生成 butyl(p-tolyl)sulfoxide
  参考文献：
  名称：

  Nucleophilic Epoxidation of α‘-Hydroxy Vinyl Sulfoxides

  摘要：

  The nucleophilic epoxidation of a variety of alpha'-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et2O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,Ss) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,Ss) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.

  DOI：

  10.1021/jo026182s
• 作为产物：
  描述：

  4-methylphenylstyryl sulfide 、 丙醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到(+/-)-(Z)-5-phenyl-4-(p-tolylsulfenyl)pent-4-en-3-ol
  参考文献：
  名称：

  手性乙烯基亚砜的不对称克莱森重排

  摘要：

  在C-5处带有手性亚砜的无环烯丙基乙烯基醚的非对映选择性克莱森重排提供了γ- δ-不饱和醛或酮，在分子中具有多达两个连续的不对称中心，同时保留了有用的乙烯基亚砜。在这项工作中还检查了相关的乙烯基硫化物和砜的反应性。

  DOI：

  10.1002/chem.200801680

文献信息

• Asymmetric Claisen Rearrangements on Chiral Vinyl Sulfoxides
  作者：Roberto Fernández de la Pradilla、Carlos Montero、Mariola Tortosa、Alma Viso

  DOI：10.1002/chem.200801680

  日期：2009.1.5

  Highly diastereoselective Claisen rearrangements of acyclic allyl vinyl ethers bearing a chiral sulfoxide at C‐5 provide γ‐δ‐unsaturated aldehydes or ketones with up to two consecutive asymmetric centers in the molecule whilst preserving a useful vinyl sulfoxide. The reactivity of related vinyl sulfides and sulfones has also been examined in this work.

  在C-5处带有手性亚砜的无环烯丙基乙烯基醚的非对映选择性克莱森重排提供了γ- δ-不饱和醛或酮，在分子中具有多达两个连续的不对称中心，同时保留了有用的乙烯基亚砜。在这项工作中还检查了相关的乙烯基硫化物和砜的反应性。
• Nucleophilic Epoxidation of α‘-Hydroxy Vinyl Sulfoxides
  作者：Roberto Fernández de la Pradilla、Jorge Fernández、Pilar Manzano、Paloma Méndez、Julián Priego、Mariola Tortosa、Alma Viso、Martín Martínez-Ripoll、Ana Rodríguez

  DOI：10.1021/jo026182s

  日期：2002.11.1

  The nucleophilic epoxidation of a variety of alpha'-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et2O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,Ss) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,Ss) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.