(1S,4R,5S,6S)-5-chloro-6-phenylsulfanylbicyclo[2.2.1]hept-2-ene | 71040-90-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1S,4R,5S,6S)-5-chloro-6-phenylsulfanylbicyclo[2.2.1]hept-2-ene
• CAS: 71040-90-9；71075-10-0
• 化学式: C₁₃H₁₃ClS
• 分子量: 236.765
• InChiKey: NDZITQUZFZUOEO-LFSVMHDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Quadricyclane 、 苯次磺酰氯 以 二氯甲烷 为溶剂， 生成 (1S,2S,3S,4R,6R)-3-Chloro-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]heptane 、 (1S,4R,5S,6S)-5-chloro-6-phenylsulfanylbicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Garratt, Dennis G.; Beaulieu, Pierre L.; Morisset, Veronique M., Canadian Journal of Chemistry, 1980, vol. 58, p. 1021 - 1029

  摘要：

  DOI：

文献信息

• A new method for the activation of ethyl benzenesulfenate in electrophilic addition reactions
  作者：N. V. Zyk、A. Yu. Gavrilova、O. A. Mukhina、O. B. Bondarenko、N. S. Zefirov

  DOI：10.1007/s11172-008-0370-7

  日期：2008.12

  Reactions of unsaturated compounds with the PhSOEt-SOHal2 and PhSOEt-Me3SiHal systems (Hal = Cl or Br) were proposed as a new route to haloalkyl phenyl sulfides. With acyclic and mono- and bicyclic alkenes and dienes as examples, the regio- and stereoselectivity of the reactions were studied.

  不饱和化合物与 PhSOEt-SOHal2 和 PhSOEt-Me3SiHal 系​​统（Hal = Cl 或 Br）的反应被提议作为制备卤代烷基苯基硫化物的新途径。以无环和单环和双环烯烃和二烯烃为例，研究了反应的区域选择性和立体选择性。
• ——
  作者：N. V. Zyk、E. K. Beloglazkina、M. A. Belova、I. F. Leshcheva、N. S. Zefirov

  DOI：10.1023/a:1020910906470

  日期：——

  The chemo-, regio- and stereoselectivities of electrophilic sulfenylation of bi-cyclo[2.2.1]hepta-2,5-diene with arenesulfenamides activated by phosphorus(v) oxohalides were studied. The ratio of the products of endo- to exo-attack of the diene by the electrophitic species depends on the solvent nature. The proportions of the products formed upon addition to one double bond and upon homoallylic participation of the second double bond depend on solvent polarity, the nature of the halogen, the substituents in the sulfenamide benzene ring, and on the reaction tune. In addition, the formation of mixed adducts was proven for the reaction carried out in acetonitrile and the formation of disulfenylation products was found in the reaction with excess sulfenylating reagent. Isomerization of exo-3-arylthio-endo-2-halo-bicyclo[2.2.1]hept-5-enes to the products formed with homoallylic participation of the second double bond, exo-5-arylthio-endo-3-halotricyclo[2.2.1.0(2,6)]heptanes, was shown to be possible.
• Beaulieu, Pierre L.; Kabo, Ann; Garratt, Dennis G., Canadian Journal of Chemistry, 1980, vol. 58, p. 1014 - 1020
  作者：Beaulieu, Pierre L.、Kabo, Ann、Garratt, Dennis G.

  DOI：——

  日期：——
• Beaulieu, Pierre L.; Morisset, Veronique M.; Garratt, Dennis G., Canadian Journal of Chemistry, 1980, vol. 58, p. 1005 - 1013
  作者：Beaulieu, Pierre L.、Morisset, Veronique M.、Garratt, Dennis G.

  DOI：——

  日期：——
• Garratt, Dennis G.; Beaulieu, Pierre L.; Morisset, Veronique M., Canadian Journal of Chemistry, 1980, vol. 58, p. 1021 - 1029
  作者：Garratt, Dennis G.、Beaulieu, Pierre L.、Morisset, Veronique M.

  DOI：——

  日期：——

表征谱图