methyl 1-benzyl-1,4,5,6-tetrahydropyridine-3-carboxylate | 75532-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 1-benzyl-1,4,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: 1-benzyl-3-methoxycarbonyl-1,4,5,6-tetrahydropyridine；methyl 1-benzyl-3,4-dihydro-2H-pyridine-5-carboxylate
• CAS: 75532-94-4
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: ODTRKAXTFXFFDR-UHFFFAOYSA-N

物化性质

• 沸点：
  354.4±42.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-1,4,5,6-tetrahydropyridine-3-carboxylate 在 sodium tetrahydroborate 、 3 Angstroem MS 、 溴 、 三乙胺 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-Benzyl-2-(benzylamino-methyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Pyrrolidines bearing a quaternary α-stereogenic center. Part 2: Access to proline chimeras, stereoselective approach and mechanistic aspects

  摘要：

  The present work describes the access to various proline chimeras bearing a quaternary cx-stereogenic center, via the Duhamel ring contraction of heterocyclic enamines. Attempts to induce diastereoselectivity are reported. The 'chiral enamine' strategy afforded the required aminoaldehydes with diastereomeric ratios as high as 85:15. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00505-0
• 作为产物：
  描述：

  烟酸甲酯 在 palladium on activated charcoal 氢气 、 silver(I) chloride 作用下， 以 甲醇 为溶剂， 生成 methyl 1-benzyl-1,4,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Pyrrolidines bearing a quaternary α-stereogenic center. Part 2: Access to proline chimeras, stereoselective approach and mechanistic aspects

  摘要：

  The present work describes the access to various proline chimeras bearing a quaternary cx-stereogenic center, via the Duhamel ring contraction of heterocyclic enamines. Attempts to induce diastereoselectivity are reported. The 'chiral enamine' strategy afforded the required aminoaldehydes with diastereomeric ratios as high as 85:15. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00505-0

文献信息

• C(sp³)–H dehydrogenation and C(sp²)–H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles
  作者：Yan He、Fang Wang、Xinying Zhang、Xuesen Fan

  DOI：10.1039/c6cc10227a

  日期：——

  A novel and efficient synthesis of tetrahydropyridine-, dihydropyrrole-, and tetrahydroazepine-3-carboxylates via cascade reactions of cyclic amines with CO and alcohols is presented. To our knowledge, this should be the first example in which functionalized N-heterocycles were prepared through Pd-catalyzed C(sp3)-H dehydrogenation and C(sp2)-H carbonylation of cyclic amines.

  通过环胺与CO和醇的级联反应，提出了一种新颖而有效的四氢吡啶-，二氢吡咯-和四氢氮杂-3-羧酸酯的合成方法。据我们所知，这应该是第一个通过钯催化环胺的C（sp 3）-H脱氢和C（sp 2）-H羰基化制备N杂环的例子。
• The synthesis of indolizidine and quinolizidine ring systems by free radical cyclization of 4-aza-6-methoxycarbonyl-5-hexenyl radicals
  作者：Athelstan L.J. Beckwith、Steven W. Westwood

  DOI：10.1016/s0040-4020(01)81101-7

  日期：1989.1

  The formation of bicyclic amines by the intramolecular cyclization of 4-aza-6-methoxycarbonyl-5-hexenyl radicals is described. The direct attachment of a nitrogen atom to the double bond changes the electronic nature of the alkene such that the cyclization is less efficient than the all carbon analogue or the other aza-substituted 5-hexenyl cyclizations.The reaction has been used in a short, convenient

  描述了通过4-氮杂-6-甲氧基羰基-5-己烯基的分子内环化形成双环胺。氮原子与双键的直接连接改变了烯烃的电子性质，因此环化的效率比全碳类似物或其他氮杂取代的5-己烯基环化的效率低。方便地从烟酸甲酯合成各种吲哚并咪唑。另外，环化被用作从烟酸甲酯短合成（±）-艾比丁宁的关键步骤。
• Paglietti, Giuseppe; Sanna, Paolo; Nuvole, Antonio, Journal of Chemical Research, Miniprint, 1983, # 10, p. 2326 - 2342
  作者：Paglietti, Giuseppe、Sanna, Paolo、Nuvole, Antonio、Soccolini, Francesco、Acheson, R. Morrin

  DOI：——

  日期：——
• Acheson, R. Morrin; Paglietti, Giuseppe, Journal of Chemical Research, Miniprint, 1981, # 10, p. 3529 - 3549
  作者：Acheson, R. Morrin、Paglietti, Giuseppe

  DOI：——

  日期：——
• BECKWITH, ATHELSTAN L. J.;WESTWOOD, STEVEN W., TETRAHEDRON, 45,(1989) N6, C. 5269-5282
  作者：BECKWITH, ATHELSTAN L. J.、WESTWOOD, STEVEN W.

  DOI：——

  日期：——