(5R,1'R,4'R)-4,5-dihydro-2-(p-chlorophenyl)-4-(phenyl)spiro[1,3,4-thiadiazolo-5,2'-camphane]

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R,1'R,4'R)-4,5-dihydro-2-(p-chlorophenyl)-4-(phenyl)spiro[1,3,4-thiadiazolo-5,2'-camphane]
• 英文别名: (1'R,2R,4'R)-5-(4-chlorophenyl)-1',7',7'-trimethyl-3-phenylspiro[1,3,4-thiadiazole-2,2'-bicyclo[2.2.1]heptane]
• 化学式: C₂₃H₂₅ClN₂S
• 分子量: 396.984
• InChiKey: CGUKBNNDPKFDPY-NLSFWIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R)-(-)-硫代樟脑 、 苯甲酰氯 4-氯苯基腙 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以74%的产率得到(5R,1'R,4'R)-4,5-dihydro-2-(p-chlorophenyl)-4-(phenyl)spiro[1,3,4-thiadiazolo-5,2'-camphane]
  参考文献：
  名称：

  Highly diastereoselective cycloaddition of diarylnitrilimines to the C˭S bond of (1R)-thiocamphor as a source of chiral spiro-1,3,4-thiadiazoles

  摘要：

  Highly diastereoselective 1,3-dipolar cycloaddition of in situ generated C,N-diaryl nitrilimines to (1R)-thiocamphor leads to chiral spiro-1,3,4-thiadiazolocamphane derivatives in good yields. The structures and stereochemistries of the new cycloadducts were fully established by spectroscopic methods including X-ray diffraction data. The diastereoselectivity observed in this reaction was explained by means of a brief theoretical study.

  DOI：

  10.1080/17415993.2012.729590