(2S)-1-[(2S, 6R)-6-methylpiperidin-2-yl]propan-2-ol | 150134-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S)-1-[(2S, 6R)-6-methylpiperidin-2-yl]propan-2-ol
• 英文别名: (+)-6-Epi-9-epipinidinol；(2S)-1-[(2S,6R)-6-methylpiperidin-2-yl]propan-2-ol
• CAS: 150134-95-5
• 化学式: C₉H₁₉NO
• 分子量: 157.256
• InChiKey: DVJHWTLBEYCZJZ-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-1-[(2S, 6R)-6-methylpiperidin-2-yl]propan-2-ol 在 potassium hydrogensulfate 作用下， 生成 (2R,6S)-2-methyl-6-(Z-2-propenyl)piperidine
  参考文献：
  名称：

  Piperidine alkaloid content of Picea pungens (Colorado blue spruce)

  摘要：

  The content and pattern of piperidine alkaloid accumulation in Picea pungens, the Colorado blue spruce, was studied as a function of growth stage and plant part. Qualitative and quantitative differences were encountered between early seedlings, mature trees, needles, stems and other plant parts. A new natural piperidine imine alkaloid, 2-methyl-6-propyl-1,6-piperideine, was found and postulated to be an intermediate leading to epidihydropinidine, the major alkaloid found in spruce needles.

  DOI：

  10.1016/0031-9422(95)00213-q
• 作为产物：
  描述：

  (2S,6R)-2-((S)-2-Hydroxy-propyl)-6-methyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester 在 10% Cd/Pd 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以53%的产率得到(2S)-1-[(2S, 6R)-6-methylpiperidin-2-yl]propan-2-ol
  参考文献：
  名称：

  反式或顺式-2,6-二取代哌啶的一般不对称路线。（+）-9-epi-6-epipinidinol和（-）-pinidinol的第一个全合成

  摘要：

  从1,6-庚二烯开始，两个AD反应以逐步方式逐步生成抗-1,5-二醇和syn -1,5-二醇立体异构体，它们已通过氨基环化反应转化为反式-和顺式-2,6二取代的哌啶（反式-和顺- 12），分别。9表- 6- epipinidinol（ - （+）的第一个全合成2）和（ - ） - pinidinol（3）已经从实现反式和-顺式- 12。

  DOI：

  10.1016/s0040-4020(98)00831-x

文献信息

• Toxic piperidine alkaloids from pine (Pinus) and spruce (Picea) trees. New structures and a biosynthetic hypothesis
  作者：Jeanne N. Tawara、Andrei Blokhin、Tommaso A. Foderaro、Frank R. Stermitz、Hakon Hope

  DOI：10.1021/jo00070a014

  日期：1993.8

  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.
• Piperidine alkaloid content of Picea pungens (Colorado blue spruce)
  作者：Fred G. Todd、Frank R. Stermitz、Andrei V. Blokhin

  DOI：10.1016/0031-9422(95)00213-q

  日期：1995.9

  The content and pattern of piperidine alkaloid accumulation in Picea pungens, the Colorado blue spruce, was studied as a function of growth stage and plant part. Qualitative and quantitative differences were encountered between early seedlings, mature trees, needles, stems and other plant parts. A new natural piperidine imine alkaloid, 2-methyl-6-propyl-1,6-piperideine, was found and postulated to be an intermediate leading to epidihydropinidine, the major alkaloid found in spruce needles.
• A general asymmetric route to trans- or cis-2,6-disubstituted piperidine. First total synthesis of (+)-9-epi-6-epipinidinol and (−)-pinidinol
  作者：Hiroki Takahata、Yasuhito Yotsui、Takefumi Momose

  DOI：10.1016/s0040-4020(98)00831-x

  日期：1998.10

  syn-1,5-diol stereodivergently, which have been converted by aminocyclization into trans- and cis-2,6-disubstituted piperidines (trans- and cis-12), respectively. The first total synthesis of (+)-9-epi-6-epipinidinol (2) and (−)-pinidinol (3) has been achieved from trans- and cis-12.

  从1,6-庚二烯开始，两个AD反应以逐步方式逐步生成抗-1,5-二醇和syn -1,5-二醇立体异构体，它们已通过氨基环化反应转化为反式-和顺式-2,6二取代的哌啶（反式-和顺- 12），分别。9表- 6- epipinidinol（ - （+）的第一个全合成2）和（ - ） - pinidinol（3）已经从实现反式和-顺式- 12。