1-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone | 274925-36-9

• 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-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone
• 英文别名: (-)-(2R,6S)-((2S)-hydroxypentyl)-6-(2'-oxopropyl)piperidine；(-)-andrachcinidine；andrachcinidine；1-[(2S,6R)-6-[(2S)-2-hydroxypentyl]piperidin-2-yl]propan-2-one
• CAS: 274925-36-9
• 化学式: C₁₃H₂₅NO₂
• 分子量: 227.347
• InChiKey: GFVMHSQLCIEXNG-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到
  参考文献：
  名称：

  Alkaloids of Andrachne aspera

  摘要：

  Two new 2,6-disubstituted piperidine alkaloids andrachcinine (1) and andrachcinidine (5) have been isolated from Andrachne aspera along with andrachamine and andrachcine (2). The absolute configurations of 1, 2, and 5 were established. (+)-Allosedridine and the new alkaloids (-)-8-epi-8-ethylnorlobelol I (4) and (-)-8-epihalosaline (7) were also identified as constituents of A. aspera. Structures were determined by MS and NMR techniques and by chemical conversions.

  DOI：

  10.1021/np9905214
• 作为产物：
  描述：

  在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到1-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone
  参考文献：
  名称：

  通过烯烃交叉复分解方案的立体选择性全合成（-）-andrachcinidine

  摘要：

  将1-立体选择性全合成（2小号，6 - [R）-6 - [（2-小号）-2-羟基戊基] -六氢-2- pyridinylacetone，（ - ） -报道andrachcinidine。该策略利用烯烃交叉复分解和分子内S N 2环化作为关键步骤。

  DOI：

  10.1016/j.tetlet.2007.08.053

文献信息

• Enantiocontrolled Synthesis of 2,6-Disubstituted Piperidines by Desymmetrization of <i>m</i><i>eso</i>-<i>η</i>-(3,4,5)-Dihydropyridinylmolybdenum Complexes. Application to the Total Synthesis of (−)-Dihydropinidine and (−)-Andrachcinidine
  作者：Chutian Shu、Lanny S. Liebeskind

  DOI：10.1021/ja029537y

  日期：2003.3.1

  A conceptually new approach to the enantiocontrolled synthesis of 2,6-disubstituted piperidines was achieved by desymmetrization of meso-2,6-dimethoxy-eta-(3,4,5)-dihydropyridinylmolybdenum complexes. After protection of the piperidine nitrogen as a urethane derived from (+)- or (-)-trans-2-(alpha-cumyl)cyclohexyl (TCC), a sequential, one-pot methoxide abstraction/nucleophilic addition/methoxide a

  2,6-二取代哌啶的对映控制合成的概念上新方法是通过meso-2,6-二甲氧基-eta-(3,4,5)-dihydropyridinylmolybdenum 配合物的去对称化实现的。将哌啶氮保护为衍生自 (+)- 或 (-)-trans-2-(α-枯基) 环己基 (TCC) 的氨基甲酸酯后，依次进行一锅甲醇提取/亲核加成/甲醇提取/亲核此外，2,6-二取代-eta-(3,4,5)-二氢吡啶基钼配合物的产率很高。该序列通过高度非对映选择性甲醇盐提取 (>40:1) 进行。高产量的原脱金属和 N-脱保护为各种 2,6-二取代哌啶提供了一种简单且对映控制的合成入口。
• Stereodivergent Synthesis of Piperidine Alkaloids by Ring-Rearrangement Metathesis/Reductive Lactam Alkylation of Nitroso Diels-Alder Cycloadducts
  作者：Guillaume Vincent、Delphine Karila、Georges Khalil、Pierre Sancibrao、Didier Gori、Cyrille Kouklovsky

  DOI：10.1002/chem.201300836

  日期：2013.7.8

  stereoselective synthesis of 2‐(2‐hydroxyalkyl)piperidine alkaloids by ring‐rearrangement metathesis of nitroso Diels–Alder cycloadducts is reported. The approach is illustrated by the formal synthesis of porantheridine and the total synthesis of andrachcinidine through a diastereodivergent allylation of an N‐alkoxy bicyclic lactam. The asymmetric synthesis of the latter alkaloid provides new insights into the configurational

  报道了通过亚硝基Diels-Alder环加成物的环重整易位立体选择性合成2-（2-羟烷基）哌啶生物碱的一般方法。通过N-烷氧基双环内酰胺的非对映异构烯丙基化的形式，通过正式合成Porantheridine和通过Andrachcinidine进行总合成，可以说明这种方法。后一种生物碱的不对称合成为氯亚硝基试剂和环戊二烯之间环加合物的构型稳定性提供了新的见解。
• Total synthesis of the 2,6-disubstituted piperidine alkaloid (−)-andrachcinidine
  作者：Palakodety Radha Krishna、Bonepally Karunakar Reddy

  DOI：10.1016/j.tetasy.2013.05.004

  日期：2013.6

  The total synthesis of the 2,6-disubstituted piperidine alkaloid (−)-andrachcinidine is reported using Keck’s asymmetric allylation, Sharpless epoxidation, nucleophilic substitution, and intramolecular aza-Michael addition as the key steps.

  据报道，使用Keck的不对称烯丙基化，Sharpless环氧化，亲核取代和分子内氮杂-Michael加成是关键步骤，合成了2,6-二取代哌啶生物碱（-）-andrachcinidine。
• A stereoselective total synthesis of (−)-andrachcinidine via an olefin cross-metathesis protocol
  作者：Palakodety Radha Krishna、G. Dayaker

  DOI：10.1016/j.tetlet.2007.08.053

  日期：2007.10

  A stereoselective total synthesis of 1-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone, (−)-andrachcinidine is reported. The strategy utilizes olefin cross-metathesis and intramolecular SN2 cyclization as the key steps.

  将1-立体选择性全合成（2小号，6 - [R）-6 - [（2-小号）-2-羟基戊基] -六氢-2- pyridinylacetone，（ - ） -报道andrachcinidine。该策略利用烯烃交叉复分解和分子内S N 2环化作为关键步骤。
• Alkaloids of <i>Andrachne aspera</i>
  作者：Sibel Mill、Claude Hootelé

  DOI：10.1021/np9905214

  日期：2000.6.1

  Two new 2,6-disubstituted piperidine alkaloids andrachcinine (1) and andrachcinidine (5) have been isolated from Andrachne aspera along with andrachamine and andrachcine (2). The absolute configurations of 1, 2, and 5 were established. (+)-Allosedridine and the new alkaloids (-)-8-epi-8-ethylnorlobelol I (4) and (-)-8-epihalosaline (7) were also identified as constituents of A. aspera. Structures were determined by MS and NMR techniques and by chemical conversions.