(E)-11-(phenylsulfonyl)-10-undecen-1-ol

• 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: (E)-11-(phenylsulfonyl)-10-undecen-1-ol
• 英文别名: (E)-11-(benzenesulfonyl)undec-10-en-1-ol
• 化学式: C₁₇H₂₆O₃S
• 分子量: 310.458
• InChiKey: OBLTZVPCALPEJQ-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  10-十一烯-1-醇 、 苯基乙烯基砜 在 Cl₂(=CH-C₆H₃-2-OiPr-5-NO₂)(1,3-dimesitylimidazolidin-2-yl)Ru 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(E)-11-(phenylsulfonyl)-10-undecen-1-ol
  参考文献：
  名称：

  乙烯基砜和亚砜的交叉复分解反应

  摘要：

  测试了在钼和钌预催化剂存在下α，β-不饱和砜和亚砜的交叉复分解反应。通过使用“第二代”钌催化剂1c - h，在官能化的末端烯烃和乙烯基砜之间实现了选择性的复分解反应，而高活性的Schrock催化剂1b是与乙烯基砜不相容的官能团。交叉复分解产物以良好的产率分离并具有优异的（E）选择性。但是，钼和钌基络合物均与α，β-和β，γ-不饱和亚砜不相容。

  DOI：

  10.1016/s0040-4020(03)00682-3

文献信息

• Cross-metathesis reaction of vinyl sulfones and sulfoxides
  作者：Anna Michrowska、Michał Bieniek、Mikhail Kim、Rafał Klajn、Karol Grela

  DOI：10.1016/s0040-4020(03)00682-3

  日期：2003.6

  Cross-metathesis reactions of α,β-unsaturated sulfones and sulfoxides in the presence of molybdenum and ruthenium pre-catalysts were tested. A selective metahesis reaction was achieved between functionalized terminal olefins and vinyl sulfones by using the ‘second generation’ ruthenium catalysts 1c–h while the highly active Schrock catalyst 1b was found to be functional group incompatible with vinyl

  测试了在钼和钌预催化剂存在下α，β-不饱和砜和亚砜的交叉复分解反应。通过使用“第二代”钌催化剂1c - h，在官能化的末端烯烃和乙烯基砜之间实现了选择性的复分解反应，而高活性的Schrock催化剂1b是与乙烯基砜不相容的官能团。交叉复分解产物以良好的产率分离并具有优异的（E）选择性。但是，钼和钌基络合物均与α，β-和β，γ-不饱和亚砜不相容。
• Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes:  Enhancement of Catalyst Activity through Electronic Activation
  作者：Anna Michrowska、Robert Bujok、Syuzanna Harutyunyan、Volodymyr Sashuk、Grigory Dolgonos、Karol Grela

  DOI：10.1021/ja048794v

  日期：2004.8.1

  The design, synthesis, stability, and catalytic activity of nitro-substituted Hoveyda-Grubbs metathesis catalysts are described. The highly active and stable meta- and para-substituted complexes are attractive from a practical point of view. These catalysts operate in very mild conditions and can be successfully applied in various types of metathesis [ring-closing metathesis, cross-metathesis (CM), and enyne metathesis]. Although the presence of a NO2 group leads to catalysts that are dramatically more active than both the second-generation Grubbs's catalyst and the phosphine-free Hoveyda's carbene, enhancement of reactivity is somewhat lower than that observed for a sterically activated Hoveyda-Grubbs catalyst. Attempts to combine two modes of activation, steric and electronic, result in severely decreasing a catalyst's stability. The present findings illustrate that different Ru catalysts turned out to be optimal for different applications. Whereas phosphine-free carbenes are catalysts of choice for CM of various electron-deficient substrates, they exhibit lower reactivity in the formation of tetrasubstituted double bonds. This demonstrates that no single catalyst outperforms all others in all possible applications.