1-piperidin-2-yl-propan-2-ol | 26171-47-1

• 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: 1-piperidin-2-yl-propan-2-ol
• 英文别名: (+)-allosedridine；(+)-Allosedridin；(2S)-1-[(2R)-Piperidin-2-yl]propan-2-ol
• CAS: 26171-47-1
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: GFKFBLJVPWRDEL-JGVFFNPUSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  244.1±13.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 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：

  聚合甲醛 、 1-piperidin-2-yl-propan-2-ol 以 水 为溶剂， 生成 3-methyl-hexahydro-pyrido[1,2-c][1,3]oxazine
  参考文献：
  名称：

  Schoepf,C. et al., Justus Liebigs Annalen der Chemie, 1970, vol. 737, p. 24 - 38

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-1-benzyloxycarbonyl-2-(2-propenyl)piperidine 在 palladium dihydroxide hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 氢气 、 三乙基硼氢化锂 作用下， 生成 1-piperidin-2-yl-propan-2-ol
  参考文献：
  名称：

  A general entry to 2-(2-hydroxyalkyl)piperidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement

  摘要：

  Both enantiomers of 2-(2-propenyl)piperidine (1) (76-88% ee), prepared via the first AD of 5-hexenyl azide, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)-piperidines (2) with enantiomeric enhancement (>98% ee). An asymmetric synthesis, starting from 2,of several 2-(2-hydroxyalkyl)piperidine alkaloids are demonstrated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00643-6

文献信息

• Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition
  作者：Stephen G. Davies、Ai M. Fletcher、Paul M. Roberts、Andrew D. Smith

  DOI：10.1016/j.tet.2009.09.104

  日期：2009.12

  Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed

  将（R）-N-烯丙基-N-（α-甲基苄基）酰胺锂或（R）-N-丁-3-烯基-N-（α-甲基苄基）酰胺共轭加成至烷基hexa-2,4 -二烯酸酯或7,6-二烯丙基烷基酯，然后在所得β-氨基酯中将烯烃官能团进行闭环复分解，以高收率生成一系列非对映异构纯的氮杂环。这些同手性模板很容易转化为景天家族的一系列哌啶生物碱，以及相应的五元，七元和八元环同系物。
• An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids
  作者：Alakesh Bisai、Vinod K. Singh

  DOI：10.1016/j.tetlet.2007.01.082

  日期：2007.3

  optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (−)-sedamine 2b, (+)- and (−)-allosedamine 2c, (+)- and (−)-sedridine 2d, (+)- and (−)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.

  我们已经开发了一种有效且通用的方法，从手性α-取代的-N-甲苯磺酰基氮丙啶开始手性的2-取代的N-甲苯磺酰基哌啶。使用这种方法，我们合成了（+）-coniine。手性的合成Ñ甲苯磺酰-2- piperidinylethanol 15和ENT - 15，由1-和d-天冬氨酸实现，分别在几个步骤。将哌啶15转化成旋光形式的2型2-（2-羟基取代）哌啶。通过应用这种策略，halosaline（的不对称合成- [R ，- [R ）- 2a中，（+） -和（ - ） - sedamine 2B，（+）-和（-）-allosedamine 2c，（+）-和（-）-三氢吡啶2d，（+）-和（-）-阿洛斯丁2e，（+）-四皂甙T-3 3a，T-4已经以高收率获得了3c，T-7 3b和T-8 3d。这些立体异构体可以通过Mitsunobu转化以优异的产率进行互转化。
• A New Synthesis of All Four Stereoisomers of 2-(2,3-Dihydroxypropyl)piperidine via Iterative Asymmetric Dihydroxylation To Cause Enantiomeric Enhancement. Application to Asymmetric Synthesis of Naturally Occurring Piperidine-Related Alkaloids
  作者：Hiroki Takahata、Minoru Kubota、Nobuo Ikota

  DOI：10.1021/jo991034w

  日期：1999.11.1

  Both enantiomers of 2-(2-propenyl)piperidine 1 (76-88% ee), prepared via the first asymmetric dihydroxylation (AD) of 5-hexenyl azide, underwent the second AD to provide all four of the stereoisomeric 2-(2,3-dihydroxypropyl)piperidines 2 with enantiomeric enhancement (>98% ee). An asymmetric synthesis, starting from 2, of several 2-(2-hydroxyalkyl)piperidine alkaloids [(-)-halosaline, (+)-N-methylallosedridine, (+)-8-ethylnorlobelol, (+)-sedridine, (+)-allosedridine, (-)-allosedridine, and (+)-N-methylsedridine] and the ant defense alkaloids [(+)-tetraponerine-3 (T-3), T-4, T-7, and T-8] is demonstrated.
• Total Synthesis of Sedum Alkaloids via Catalyst Controlled aza-Cope Rearrangement and Hydroformylation with Formaldehyde
  作者：Hong Ren、William D. Wulff

  DOI：10.1021/ol302769r

  日期：2013.1.18

  The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.
• Short enantioselective synthesis of sedridines, ethylnorlobelols and coniine via reagent-based differentiation
  作者：Daniele Passarella、Alessio Barilli、Francesca Belinghieri、Paola Fassi、Sergio Riva、Alessandro Sacchetti、Alessandra Silvani、Bruno Danieli

  DOI：10.1016/j.tetasy.2005.05.032

  日期：2005.7

  The preparation of collections of structurally diverse small molecules is a useful tool for studying biology and medicine with chemistry. Herein, we demonstrate the versatility of the pure enantiomers of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tertbutyl ester to prepare the biological active alkaloids sedridine, allosedridine, methylsedridine, methylallosedridine, ethylnorlobelol, and coniine in two steps and in a stereoselective way via a reagent-based differentiation. The described syntheses are a demonstration of the versatility of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl esters as chiral building blocks. (c) 2005 Elsevier Ltd. All rights reserved.