((1S,2S,3S,4R)-3-chlorobicyclo[2.2.1]hept-5-en-2-yl)(2-nitrophenyl)sulfane | 71040-85-2

• 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: ((1S,2S,3S,4R)-3-chlorobicyclo[2.2.1]hept-5-en-2-yl)(2-nitrophenyl)sulfane
• CAS: 71040-85-2
• 化学式: C₁₃H₁₂ClNO₂S
• 分子量: 281.763
• InChiKey: HJQMTDNJTIFYQE-FQPOAREZSA-N

物化性质

• 沸点：
  423.2±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,5-Norbornadiene 、 2-硝基苯硫氯 以 四氯化碳 为溶剂， 生成 ((1S,2S,3S,4R)-3-chlorobicyclo[2.2.1]hept-5-en-2-yl)(2-nitrophenyl)sulfane 、 (1R,4S,5S,6S)-5-Chloro-6-(2-nitro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-ene 、 (1S,2S,3R,4R,5R,6R)-3-Chloro-5-(2-nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1020910906470

文献信息

• Garratt, Dennis G.; Przybylska, Maria; Cygler, Miroslaw, Canadian Journal of Chemistry, 1983, vol. 61, p. 1176 - 1184
  作者：Garratt, Dennis G.、Przybylska, Maria、Cygler, Miroslaw

  DOI：——

  日期：——
• Reaction of 2,4-dinitrobenzenesulfenyl chloride with quadricyclene
  作者：N. S. Zefirov、N. K. Sadovaya、T. N. Velikokhat'ko、L. A. Andreeva、Terence C. Morrill

  DOI：10.1021/jo00347a018

  日期：1982.4
• Zefirov, N. S.; Sadovaya, N. K.; Akhmedova, R. Sh., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 503 - 510
  作者：Zefirov, N. S.、Sadovaya, N. K.、Akhmedova, R. Sh.、Bodrikov, I. V.、Morrill, T. C.、et al.

  DOI：——

  日期：——
• 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：——