(E)-1-(phenylsulfonyl)-1-hexen-6-ol | 136277-41-3

• 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)-1-(phenylsulfonyl)-1-hexen-6-ol
• 英文别名: (E)-6-(phenylsulfonyl)-5-hexen-1-ol；(E)-6-(benzenesulfonyl)hex-5-en-1-ol
• CAS: 136277-41-3
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: YFGAZVFWKXDLLS-YRNVUSSQSA-N

物化性质

• 沸点：
  443.8±45.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (E)-1-(phenylsulfonyl)-1-hexen-6-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 (E)-6-Benzenesulfonyl-hex-5-enal
  参考文献：
  名称：

  Intramolecular palladium-catalyzed trimethylenemethane cycloadditions: initial studies

  摘要：

  The potential application of [3 + 2] cycloadditions to polycarbocycle construction is considerably enhanced by the ability to perform such reactions intramolecularly. The feasibility of such processes is explored in the context of Pd-catalyzed cycloadditions of 2-[(trimethylsilyl)methyl]allyl carboxylates, wherein trimethylenemethane (TMM) precursor fragment (donor) and the electron-deficient olefin (acceptor) is joined by a tether of simple methylene groups of 3, 4, 5, and 8 members. Several versatile synthetic routes to these substrates were developed. 2-Bromo-3-(trimethylsilyl)propene proves to be a key reagent for construction of the donor portion. Acceptors bearing esters, cyano groups, and especially sulfones have been examined. The diastereoselectivity of the reaction has been explored both in terms of ring juncture and the diastereofacial selectivity with respect to an oxygen substituent at the allylic position of the acceptor. Excellent cycloadditions to give the bicyclo[3.3.0] octyl and bicyclo[4.3.0]nonyl systems are observed, whereas larger rings cannot be obtained in this series. The choice of catalyst proves critical, the most useful being either tetrakis(triphenylphosphine)palladium and DPPE or, more generally, triisopropyl phosphite and palladium acetate. The first cycloaddition of a 1,1-dialkylated TMM precursor, which fails in intermolecular cases, has been observed in this intramolecular series to give a bridgehead-substituted bicycle. A rationale for the observed diastereoselectivity is presented.

  DOI：

  10.1021/ja00019a036
• 作为产物：
  描述：

  5-己烯-1-醇 、 苯基乙烯基砜 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(E)-1-(phenylsulfonyl)-1-hexen-6-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

• Highly selective cross-metathesis with phenyl vinyl sulphone using the ‘second generation’ Grubbs’ catalyst
  作者：Karol Grela、Michał Bieniek

  DOI：10.1016/s0040-4039(01)01269-2

  日期：2001.9

  A cross-metathesis reaction was achieved between functionalised terminal olefins and phenyl vinyl sulfone by using the commercially available ruthenium catalyst Ile. The cross-metathesis products were isolated in moderate to good yield with excellent (E)-stereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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。
• Intramolecular palladium-catalyzed trimethylenemethane cycloadditions: initial studies
  作者：Barry M. Trost、Timothy A. Grese、Dominic M. T. Chan

  DOI：10.1021/ja00019a036

  日期：1991.9

  The potential application of [3 + 2] cycloadditions to polycarbocycle construction is considerably enhanced by the ability to perform such reactions intramolecularly. The feasibility of such processes is explored in the context of Pd-catalyzed cycloadditions of 2-[(trimethylsilyl)methyl]allyl carboxylates, wherein trimethylenemethane (TMM) precursor fragment (donor) and the electron-deficient olefin (acceptor) is joined by a tether of simple methylene groups of 3, 4, 5, and 8 members. Several versatile synthetic routes to these substrates were developed. 2-Bromo-3-(trimethylsilyl)propene proves to be a key reagent for construction of the donor portion. Acceptors bearing esters, cyano groups, and especially sulfones have been examined. The diastereoselectivity of the reaction has been explored both in terms of ring juncture and the diastereofacial selectivity with respect to an oxygen substituent at the allylic position of the acceptor. Excellent cycloadditions to give the bicyclo[3.3.0] octyl and bicyclo[4.3.0]nonyl systems are observed, whereas larger rings cannot be obtained in this series. The choice of catalyst proves critical, the most useful being either tetrakis(triphenylphosphine)palladium and DPPE or, more generally, triisopropyl phosphite and palladium acetate. The first cycloaddition of a 1,1-dialkylated TMM precursor, which fails in intermolecular cases, has been observed in this intramolecular series to give a bridgehead-substituted bicycle. A rationale for the observed diastereoselectivity is presented.