(1R,7R)-6,7-dimethyl-3-(4-methylphenyl)sulfonyl-3-azatricyclo[5.2.1.01,5]dec-5-ene | 909704-88-7

• 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: (1R,7R)-6,7-dimethyl-3-(4-methylphenyl)sulfonyl-3-azatricyclo[5.2.1.01,5]dec-5-ene
• CAS: 909704-88-7
• 化学式: C₁₈H₂₃NO₂S
• 分子量: 317.452
• InChiKey: FXIQTRVFUJTSQD-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,7R)-6,7-dimethyl-3-(4-methylphenyl)sulfonyl-3-azatricyclo[5.2.1.01,5]dec-5-ene 在 臭氧 、 二甲基硫 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以72%的产率得到7-aceto-7-methyl-2-tosyl-2-azaspiro[4.4]nonan-4-one
  参考文献：
  名称：

  Enantioselective Syntheses of Various Chiral Multicyclic Compounds with Quaternary Carbon Stereocenters by Catalytic Intramolecular Cycloaddition

  摘要：

  The intramolecular cycloaddition of 1,n-diene-ynes (n = 4-6), where alkyne and alkene moieties are connected by a 1,1-disubstituted alkene, was examined using a chiral rhodium catalyst, and various types of cycloadducts with quaternary carbon stereocenter(s) were obtained in high to excellent enantiomeric excess. In the case of 1,4-diene-ynes, tricyclic, bicyclic, and spirocyclic compounds were obtained depending upon the substituents at the 2-position of the 1,4-diene moiety and those at their alkyne termini. On the other hand, 1,5- and 1,6-diene-ynes gave tricyclic and bicyclic compounds, which included medium-sized ring systems. The mechanistic considerations for different reaction pathways and the synthetic transformation of tricyclic products into functionalized spirocyclic compounds are also described. The reaction of enediynes, where two alkyne moieties are connected by a 1,1-disubstituted alkene, was also examined, and sterically strained tricyclic compounds with two carbon stereocenters were obtained.

  DOI：

  10.1021/ja0762083
• 作为产物：
  描述：

  N-(but-2-ynyl)-4-methyl-2-methylene-N-tosylpent-4-en-1-amine 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以81%的产率得到(1R,7R)-6,7-dimethyl-3-(4-methylphenyl)sulfonyl-3-azatricyclo[5.2.1.01,5]dec-5-ene
  参考文献：
  名称：

  1,4-二烯-炔的对映选择性分子内[2 + 2 + 2]环加成：构建季碳立体中心的新方法

  摘要：

  使用手性铑催化剂检查了各种 1,4-二烯-炔的分子内 [2 + 2 + 2] 环加成。在 1,4-二烯部分的 2-位具有取代基的 1,4-二烯-炔的情况下，具有应变双环 [2.2.1] 庚烯骨架和两个季碳立体中心的三环化合物以高对映体过量。另一方面，在该位置没有取代基的 1,4-二烯-炔的情况下，可能通过反应中间体的碳-碳键断裂获得具有季碳立体中心的双环环六-1,3-二烯。

  DOI：

  10.1021/ja0639160