甲基1-甲基-1,4-二氢-3-吡啶羧酸酯 | 59138-83-9

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 甲基1-甲基-1,4-二氢-3-吡啶羧酸酯
• 英文名称: 1-methyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
• 英文别名: methyl N-methyl-1,4-dihydro-nicotinate；Methyl 1-methyl-1,4-dihydropyridine-3-carboxylate；methyl 1-methyl-4H-pyridine-3-carboxylate
• CAS: 59138-83-9
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: UJTANRJAPQJTLF-UHFFFAOYSA-N

物化性质

• 沸点：
  224.2±40.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  甲基1-甲基-1,4-二氢-3-吡啶羧酸酯 在 叠氮基三甲基硅烷 、 bis(collidine)iodonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以66%的产率得到Methyl trans-2-azido-3-iodo-1-methyl-1,2,3,4-tetrahydropyridine-5-carboxylate
  参考文献：
  名称：

  Introduction of Heteroatom-Based Substituents into 1,4-Dihydropyridines by Means of a Halogen-Mediated, Oxidative Protocol: Diamination, Sulfonylation, Sulfinylation, Bis-Sulfanylation, and Halo-Phosphonylation Processes

  摘要：

  The natural tendency of 1,4-dihydropyridines to undergo "biomimetic" oxidation to afford pyridinium salts can be switched off and, through the use of reagents that interact electrophilically with the enamine moiety present in the heterocyclic system, it is possible to promote alternative oxidations. In this way, efficient regio- and stereocontrolled synthetic methods have been developed that lead to diversely substituted di- and tetrahydropyridines. These include iodoazidation, diamination, bis-sulfonamidation, sulfonylation, sulfinylation, thiocyanation, sulfanylation, bis-sulfanylation, and halo-phosphonylation processes.

  DOI：

  10.1002/(sici)1521-3765(20000515)6:10<1763::aid-chem1763>3.0.co;2-r
• 作为产物：
  描述：

  3-(甲氧羰基)-1-甲基吡啶碘化物 在 sodium dithionite 、 碳酸氢钠 作用下， 生成 甲基1-甲基-1,4-二氢-3-吡啶羧酸酯
  参考文献：
  名称：

  WO2007/38772

  摘要：

  公开号：

文献信息

• Dihydropyridine-Based Multicomponent Reactions. Efficient Entry into New Tetrahydroquinoline Systems through Lewis Acid-Catalyzed Formal [4 + 2] Cycloadditions
  作者：Rodolfo Lavilla、M. Carmen Bernabeu、Inés Carranco、José Luis Díaz

  DOI：10.1021/ol027545d

  日期：2003.3.1

  tetrahydroquinolines in a stereoselective manner through a Lewis acid-catalyzed formal [4 + 2] cycloaddition. InCl(3) and Sc(OTf)(3) are the catalysts of choice for this process. The in situ generation of a reactive 1,4-dihydropyridine through the regioselective nucleophilic addition of cyanide to pyridinium salts allows a one-pot four-component transformation.

  二氢吡啶，醛和对甲基苯胺的三组分反应通过路易斯酸催化的正式[4 + 2]环加成反应，以立体选择性方式高效形成高度取代的四氢喹啉。InCl（3）和Sc（OTf）（3）是该工艺的选择催化剂。通过将氰化物的区域选择性亲核加成到吡啶鎓盐中而原位产生反应性1,4-二氢吡啶可实现一锅四组分转化。
• Non-biomimetic oxidation of 1,4-dihydropyridines
  作者：Rodolfo Lavilla、Francisco Gullón、Xavier Barón、Joan Bosch

  DOI：10.1039/a606919c

  日期：——

  The reaction between N-alkyl-1,4-dihydropyridines and dimethyldioxirane leads to dimeric tetrahydropyridines having oxygen atoms at the 2- and 3-positions in good yields and with good stereocontrol; these compounds are useful iminium ion precursors, and are satisfactorily transformed into 2-substituted 3-hydroxy-1,2,3,4-tetrahydropyridines.

  N-烷基-1,4-二氢吡啶与二甲基二氧环烯的反应生成了具有良好产率和良好立体选择性的含氧二聚体四氢吡啶，这些化合物是有用的亚硝基离子前体，并能令人满意地转化为2-取代的3-羟基-1,2,3,4-四氢吡啶。
• Oxidative Additions with 1,4-Dihydropyridines: A One-Pot Synthesis of 3,4,4a,5,8,8a-Hexahydro-2<i>H</i>-pyrido[3,2-b][1,4]oxazine Derivatives
  作者：Rakesh Kumar、Shakshi Malik、Dhiraj Kumar、Ashok K. Prasad

  DOI：10.1080/00397911.2010.515348

  日期：2011.9.15

  4a,5,8,8a-Hexahydro-2H-pyrido[3,2-b][1,4]oxazine derivatives (2a–h) are conveniently prepared in excellent yields by a one-pot synthesis from 1,4-dihydropyridines. The key transformation features an electrophilic interaction of iodine with N-alkyl-1,4-dihydropyridine (1a–d) in the presence of a nucleophile diethanol amine or N-methylethanol amine, stereoselectively leading to the corresponding bicyclic

  摘要 3,4,4a,5,8,8a-Hexahydro-2H-pyrido[3,2-b][1,4]oxazine 衍生物 (2a–h) 1,4-二氢吡啶。关键转化的特点是在亲核二乙醇胺或 N-甲基乙醇胺存在下，碘与 N-烷基-1,4-二氢吡啶（1a-d）的亲电相互作用，立体选择性地产生相应的双环杂环（2a-h） .
• Multifunctional Compounds and Methods of Use Thereof
  申请人：Kador Peter F.

  公开号：US20090105269A1

  公开（公告）日：2009-04-23

  Compositions comprising multifunctional agents and methods of use thereof are provided.

  提供了包含多功能剂的组合物和使用方法。
• Vicinal diamination of 1,4-dihydropyridines
  作者：Rodolfo Lavilla、Rakesh Kumar、Oscar Coll、Carme Masdeu、Joan Bosch

  DOI：10.1039/a807776b

  日期：——

  Electrophilic interaction of iodine with N-alkyl-1,4-dihydropyridines 1 in the presence of secondary amines stereoselectively leads to the corresponding trans-2,3-diamino-1,2,3,4-tetrahydropyridines 2 in satisfactory yields (79–94%); the method allows the synthesis of piperidine, pyrrolidine, morpholine and piperazine derivatives.

  在仲胺存在下，碘与N-烷基-1,4-二氢吡啶1的亲电相互作用可立体选择性生成相应的反式-2,3-二氨基-1,2,3,4-四氢吡啶2，收率令人满意（79-94%）；该方法可用于合成哌啶、吡咯烷、吗啉和哌嗪衍生物。

表征谱图