(2R,6S)-2-烯丙基-6-苯基-1,2,3,6-四氢吡啶 | 175478-20-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (2R,6S)-2-烯丙基-6-苯基-1,2,3,6-四氢吡啶
• 英文名称: trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine
• 英文别名: (2R,6S)-6-phenyl-2-prop-2-enyl-1,2,3,6-tetrahydropyridine
• CAS: 175478-20-3
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: XEDAFXCBQWHDQW-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,6S)-2-烯丙基-6-苯基-1,2,3,6-四氢吡啶 在 三烯丙基硼烷 、 氢氧化钾 作用下， 生成 (2S,6S)-2-Allyl-6-phenyl-1,2,3,6-tetrahydro-pyridine
  参考文献：
  名称：

  基于吡啶的还原反式-2,6-二烷基化反应制备反-顺-2-烯丙基-6-烷基（芳基）-1,2,3,6-四氢吡啶。(±)-表二氢吡啶和(±)-二氢吡啶的合成

  摘要：

  基于 RLi 与吡啶的 1,2-加成和三烯丙基硼烷的反式-6-烯丙基化的组合制备不对称反式-2-烯丙基-6-烷基（芳基）-1,2,3,6-四氢吡啶6的一般方法在甲醇的存在下进行了详细说明。结果表明，反式哌啶（6（R = Alk，Ph）在与三烯丙基硼烷一起加热时异构化为相应的顺式-2-烯丙基-6-烷基（苯基）-3-哌啶14，然后用甲醇和氨基硼烷（16）脱硼碱。化合物 6 和 14 的立体化学由二维 NOE 光谱测定。讨论了形成反式胺 6 及其转化为顺式异构体 14 的可能机制。生物碱 (±)-表二氢吡啶（反式 2-甲基-6-丙基哌啶 2a , 70%) 和 (±)-dihydropinidine (cis-2-methyl-6-propylpiperidine1d,

  DOI：

  10.1007/bf02495652
• 作为产物：
  描述：

  吡啶 、 三烯丙基硼烷 、 苯基锂 在 sodium hydroxide 作用下， 生成 2-苯基吡啶 、 (2R,6S)-2-烯丙基-6-苯基-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  基于吡啶的还原反式-2,6-二烷基化反应制备反-顺-2-烯丙基-6-烷基（芳基）-1,2,3,6-四氢吡啶。(±)-表二氢吡啶和(±)-二氢吡啶的合成

  摘要：

  基于 RLi 与吡啶的 1,2-加成和三烯丙基硼烷的反式-6-烯丙基化的组合制备不对称反式-2-烯丙基-6-烷基（芳基）-1,2,3,6-四氢吡啶6的一般方法在甲醇的存在下进行了详细说明。结果表明，反式哌啶（6（R = Alk，Ph）在与三烯丙基硼烷一起加热时异构化为相应的顺式-2-烯丙基-6-烷基（苯基）-3-哌啶14，然后用甲醇和氨基硼烷（16）脱硼碱。化合物 6 和 14 的立体化学由二维 NOE 光谱测定。讨论了形成反式胺 6 及其转化为顺式异构体 14 的可能机制。生物碱 (±)-表二氢吡啶（反式 2-甲基-6-丙基哌啶 2a , 70%) 和 (±)-dihydropinidine (cis-2-methyl-6-propylpiperidine1d,

  DOI：

  10.1007/bf02495652

文献信息

• Efficient Approaches for the Synthesis of Diverse α-Diazo Amides
  作者：Adam Nelson、Shiao Chow、Adam I. Green、Christopher Arter、Samuel Liver、Abbie Leggott、Luke Trask、George Karageorgis、Stuart Warriner

  DOI：10.1055/s-0039-1690905

  日期：2020.6

  chemistry can be exploited for the synthesis of diverse ranges of small molecules from α-diazo carbonyl compounds. In this paper, three synthetic approaches to α-diazo amides are described, and their scope and limitations are determined. On the basis of these synthetic studies, recommendations are provided to assist the selection of the most appropriate approach for specific classes of product. The

  金属催化的类胡萝卜素化学可用于从α-重氮羰基化合物合成各种范围的小分子。本文描述了三种合成α-重氮酰胺的方法，并确定了它们的范围和局限性。在这些综合研究的基础上，提供了建议，以帮助针对特定类别的产品选择最合适的方法。各种不同的α-重氮乙酰胺的实用，有效的合成方法有望促进发现许多不同类别的生物活性小分子。
• Preparation of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines by reductive trans-2,6-dialkylation of pyridine. Synthesis of (±)-epidihydropinidine
  作者：Yuri N Bubnov、Elena V Klimkina、Anatoly V Ignatenko、Ilya D Gridnev

  DOI：10.1016/0040-4039(95)02383-6

  日期：1996.2

  A convenient method for the preparation of the title compounds involving the sequential treatment of pyridine with RLi (R = Alk, Ar), triallylborane and methanol is developed.

  开发了一种方便的制备标题化合物的方法，该方法涉及用RLi（R = Alk，Ar），三烯丙基硼烷和甲醇依次处理吡啶。
• Synthesis and molecular structure oftrans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
  作者：Yu. N. Bubnov、E. V. Klimkina、M. O. Dekaprilevich、Yu. T. Strruchkov

  DOI：10.1007/bf01431124

  日期：1996.11

  When treated with triallylborane and MeOH, the product of the 1,2-addition of PhLi to pyridine transforms to trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine. The structure of its hydrochloride was established by X-ray structural analysis.
• ——
  作者：L. M. Korotayeva、T. Ya. Rubinskaya、E. V. Klimkina、V. P. Gultyai、Yu. N. Bubnov

  DOI：10.1023/a:1009580110623

  日期：——

  Electrochemical reduction of trans-2-allyl-6-R-1,2,3,6-tetrahydropyridines (R = Me, All, and Ph) on the mercury cathode in anhydrous DMF (with 0.1 M Bu4NClO4 as the supporting electrolyte) resulted in catalytic hydrogen evolution, while in the case of anhydrous DMF the electrochemical activity of the endocyclic double bond was dictated by the nature of the R substituent at the carbon atom neighboring the double bond. The electrocatalytic hydrogenation of the piperideines under study on the Ni (Ni-disp/Ni) cathode in 40%; aqueous DMF in the presence of a tenfold excess of AcOH yielded the corresponding trans-2-propyl-6-R-1 piperidines (R-1 = Me, Pr, acid Ph). Using trans-2,6-diallyl-1,2,3,6-tetrahydropyridine as an example, the conditions (with annealed copper as the cathode) for selective hydrogenation of the double bonds in allyl substituents with preservation of the endocyclic double bond were found.
• Preparative electroreduction oftrans-2-allyl-6-methyl(phenyl)-1,2,3,6-tetrahydropyridine
  作者：L. M. Korotayeva、T. Ya. Rubinskaya、E. V. Klimkina、V. P. Gultyai、Yu. N. Bubnov

  DOI：10.1007/bf02496263

  日期：1999.4

  Electrocatalytic hydrogenation of trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine and trans-2-allyl-6-methyl-1,2,3,6-tetrahydropyridine in 40% aqueous DMF in the presence of AcOH on a nickel cathode gave trans-6-phenyl-2-propylpiperidine and trans-2-methyl-6-propylpiperidine ((+/-)-epidihydropinidine), respectively. Direct electroreduction of trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine in anhydrous DMF on a mercury cathode afforded a 7 : 5 mixture of trans- and cis-2-allyl-6-phenylpiperidine. The structure of the latter compound was confirmed by 2D NOESY spectroscopy. The possible mechanism of formation of the cis-isomer is discussed.