(+/-)-(Z)-4-(p-tolylsulfonyl)non-4-en-3-ol | 479623-94-4

• 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: (+/-)-(Z)-4-(p-tolylsulfonyl)non-4-en-3-ol
• 英文别名: (Z)-4-(4-methylphenyl)sulfonylnon-4-en-3-ol
• CAS: 479623-94-4
• 化学式: C₁₆H₂₄O₃S
• 分子量: 296.431
• InChiKey: WWOQUTSAVVAIEN-PXNMLYILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(Z)-4-(p-tolylsulfonyl)non-4-en-3-ol 在 叔丁基过氧化氢 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以62%的产率得到(+/-)-(1'S,2R,3S)-3-n-butyl-2-(1'-hydroxypropyl)-2-(p-tolylsulfonyl)oxirane
  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：

  (+/-)-(Z)-4-(p-tolylsulfenyl)non-4-en-2-ol 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以74%的产率得到(+/-)-(Z)-4-(p-tolylsulfonyl)non-4-en-3-ol
  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

文献信息

• 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.