(+)-1,2-Dehydropinidinol | 150044-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (+)-1,2-Dehydropinidinol
• 英文别名: (2R)-1-[(2R)-6-methyl-2,3,4,5-tetrahydropyridin-2-yl]propan-2-ol
• CAS: 150044-65-8
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: BVHCJQPMRVMDBC-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-1,2-Dehydropinidinol 在 lithium aluminium tetrahydride 、 三甲基铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以50%的产率得到(-)-pinidinol
  参考文献：
  名称：

  Toxic piperidine alkaloids from pine (Pinus) and spruce (Picea) trees. New structures and a biosynthetic hypothesis

  摘要：

  A series of 2,6-disubstituted piperidine alkaloids have been isolated from several Pinus (pine) and Picea (spruce) species and characterized structurally. The pines appear to contain only cis-disubstituted piperidines, while the spruces contain both cis- and trans-disubstituted piperidines. The structural relationships among the alkaloids suggest a plausible biosynthetic scheme and a reason why previous attempts to elucidate the biosynthesis of pinidine failed beyond establishing its polyketide origin. A mixture of alkaloids from needles of Pinus ponderosa proved to be highly teratogenic. The alkaloids might therefore be involved in so-called pine needle abortion which occurs in pregnant range cows which feed on Ponderosa pine needles.

  DOI：

  10.1021/jo00070a014
• 作为产物：
  描述：

  (-)-pinidinol 在 sodium hydroxide 、 次氯酸叔丁酯 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 苯 为溶剂， 反应 1.5h， 生成 (+)-1,2-Dehydropinidinol
  参考文献：
  名称：

  Toxic piperidine alkaloids from pine (Pinus) and spruce (Picea) trees. New structures and a biosynthetic hypothesis

  摘要：

  A series of 2,6-disubstituted piperidine alkaloids have been isolated from several Pinus (pine) and Picea (spruce) species and characterized structurally. The pines appear to contain only cis-disubstituted piperidines, while the spruces contain both cis- and trans-disubstituted piperidines. The structural relationships among the alkaloids suggest a plausible biosynthetic scheme and a reason why previous attempts to elucidate the biosynthesis of pinidine failed beyond establishing its polyketide origin. A mixture of alkaloids from needles of Pinus ponderosa proved to be highly teratogenic. The alkaloids might therefore be involved in so-called pine needle abortion which occurs in pregnant range cows which feed on Ponderosa pine needles.

  DOI：

  10.1021/jo00070a014