(±)-(R*)-oxazol-2-yl((1R*,4aR*,8aR*)-4a-vinyldecahydronaphthalen-1-yl)methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (±)-(R*)-oxazol-2-yl((1R*,4aR*,8aR*)-4a-vinyldecahydronaphthalen-1-yl)methanol
• 英文别名: (R)-[(1R,4aR,8aR)-4a-ethenyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-1-yl]-(1,3-oxazol-2-yl)methanol
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: ZAKPTQXIUUQJMT-IXYNUQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  萘烷 在 aluminum (III) chloride 、 正丁基锂 、 硼烷四氢呋喃络合物 、 草酰氯 、 硫酸 、 potassium tert-butylate 、 对甲苯磺酸 、 二甲基亚砜 、 9λ²-borabicyclo[3.3.1]nonane 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 44.25h， 生成 (±)-(R*)-oxazol-2-yl((1R*,4aR*,8aR*)-4a-vinyldecahydronaphthalen-1-yl)methanol 、 (±)-(S*)-oxazol-2-yl((1R*,4aR*,8aR*)-4a-vinyldecahydronaphthalen-1-yl)methanol
  参考文献：
  名称：

  A Model System for the Synthesis of Complanadine Alkaloids by “Diverted Kondrat’eva” Oxazole–Olefin Cycloaddition

  摘要：

  A synthetic approach to complanadine alkaloids is described which employs a Kondrat'eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole a-hydroxy group as an active participant in the cycloadduct fragmentation process.

  DOI：

  10.1021/jo401014n

文献信息

• A Model System for the Synthesis of Complanadine Alkaloids by “Diverted Kondrat’eva” Oxazole–Olefin Cycloaddition
  作者：Mario Uosis-Martin、G. Dan Pantoş、Mary F. Mahon、Simon E. Lewis

  DOI：10.1021/jo401014n

  日期：2013.6.21

  A synthetic approach to complanadine alkaloids is described which employs a Kondrat'eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole a-hydroxy group as an active participant in the cycloadduct fragmentation process.