甲基6-甲氧基-3,6-二氢-1(2H)-吡啶羧酸酯 | 114523-69-2

• 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6-甲氧基-3,6-二氢-1(2H)-吡啶羧酸酯
• 英文名称: 1-methoxycarbonyl-2-methoxy-1,2,5,6-tetrahydropyridine
• 英文别名: 3,4-didehydro-2-methoxy-1-methoxycarbonylpiperidine；3,4-didehydro-N-methoxycarbonyl-2-methoxypiperidine；methyl 6-methoxy-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 114523-69-2
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: GUJONRXISVYHIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基6-甲氧基-3,6-二氢-1(2H)-吡啶羧酸酯 在 镍 氢气 、 四氯化钛 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Dimethyl 2-(1-methoxycarbonylpiperidin-4-yl)propanedioate
  参考文献：
  名称：

  区域和立体选择性地将双（甲氧基羰基）甲基引入哌啶骨架的γ位

  摘要：

  探索了将双（甲氧基羰基）-甲基区域选择性地引入哌啶骨架的4-位的新方法，并将该方法用于制备从-开始的顺式和反式-2,4-二取代的哌啶2-哌啶羧酸。该方法的关键步骤涉及氨基甲酸酯的电化学氧化。

  DOI：

  10.1016/0040-4039(96)01208-7
• 作为产物：
  描述：

  甲基3,4-二氢-1(2H)-吡啶羧酸酯 在 溴 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 甲基6-甲氧基-3,6-二氢-1(2H)-吡啶羧酸酯
  参考文献：
  名称：

  区域选择性合成2-取代的1-（甲氧羰基）-1，2-二氢吡啶的新方法

  摘要：

  由2-取代的哌啶通过三种中间体，即（a）1,2,3,4-四氢吡啶，（b）5-溴-6-，区域选择性地制备包括光学活性的2-取代的1,2-二氢吡啶。甲氧基哌啶，和（c）1,2,3,6-四氢-6-甲氧基吡啶。

  DOI：

  10.1016/s0040-4039(01)83864-8

文献信息

• A new method for regioselective synthesis of 2-substituted 1-(methoxycarbonyl)-1,2-dihydropyridines
  作者：Tatsuya Shono、Yoshihiro Matsumura、Osamu Onomura、Yasufu Yamada

  DOI：10.1016/s0040-4039(01)83864-8

  日期：1987.1

  2-Substituted 1,2-dihydropyridines including an optically active one were regioselectively prepared from 2-substituted piperidines through three intermediates, that is, (a) 1,2,3,4-tetrahydropyridines, (b) 5-bromo-6-methoxypiperidines, and (c) 1,2,3,6-tetrahydro- 6-methoxypyridines.

  由2-取代的哌啶通过三种中间体，即（a）1,2,3,4-四氢吡啶，（b）5-溴-6-，区域选择性地制备包括光学活性的2-取代的1,2-二氢吡啶。甲氧基哌啶，和（c）1,2,3,6-四氢-6-甲氧基吡啶。
• Indium-mediated nucleophilic substitution reaction of β,γ-unsaturated α-methoxypiperidine derivative in water
  作者：Yoshihiro Matsumura、Osamu Onomura、Hideaki Suzuki、Shigeru Furukubo、Toshihide Maki、Chao-Jun Li

  DOI：10.1016/s0040-4039(03)01042-6

  日期：2003.7

  Water as a solvent was found to accelerate the indium-mediated Barbier type allylation and benzylation of beta,gamma-unsaturated piperidinium ion which was generated from beta,gamma-unsaturated alpha-methoxy-N-methoxycarbonylpiperidine, while ring-opened allylated product was obtained in a case using beta,gamma-saturated alpha-methoxy-N-methoxycarbonylpiperidine. Other solvents than water resulted in low yield of the allylated and benzylated products, suggesting that water is essential to generate the piperidinium ion intermediate from beta,gamma-unsaturated alpha-methoxy-N-methoxycarbonylpiperidine. (C) 2003 Published by Elsevier Science Ltd.
• Stereoselective synthesis of azasugars by electrochemical oxidation
  作者：Shigeru Furukubo、Noriaki Moriyama、Osamu Onomura、Yoshihiro Matsumura

  DOI：10.1016/j.tetlet.2004.09.036

  日期：2004.10

  A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was Successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
  作者：Noriaki Moriyama、Yoshihiro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2009.11.028

  日期：2009.12

  A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxpiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-(3-triacetoxy-(5S)-methylpiperidine. (C) 2009 Elsevier Ltd. All rights reserved.
• Regioselective introduction of alkyl groups to the position α or γ to nitrogen atom of piperidine skeletons using anodic oxidation in a key step
  作者：Tatsuya Shono、Sun Terauchi、Yoshihisa Ohki、Yoshihiro Matsumura

  DOI：10.1016/s0040-4039(00)97071-0

  日期：1990.1