β-bromo-α-methoxy-N-(methoxycarbonyl)piperidine | 113718-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: β-bromo-α-methoxy-N-(methoxycarbonyl)piperidine
• 英文别名: β-bromo-α-methoxy-N-methoxycarbonylpiperidine；3-bromo-2-methoxy-1-methoxycarbonylpiperidine；Methyl 3-bromo-2-methoxypiperidine-1-carboxylate
• CAS: 113718-34-6
• 化学式: C₈H₁₄BrNO₃
• 分子量: 252.108
• InChiKey: YSZAMLRAOVWDMX-UHFFFAOYSA-N

物化性质

• 沸点：
  289.6±40.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  β-bromo-α-methoxy-N-(methoxycarbonyl)piperidine 在 溴化铵 electrochem. generated 2-pyrrolidine anion 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 25.0~100.0 ℃ 、13.33 kPa 条件下， 反应 2.0h， 生成 1,2-二氢-1-吡啶羧酸甲酯
  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
• 作为产物：
  描述：

  甲基3,4-二氢-1(2H)-吡啶羧酸酯 以80%的产率得到
  参考文献：
  名称：

  SHONO, TATSUYA;TERAUCHI, JUN;OHKI, YOSHIHISA;MATSUMURA, YOSHIHIRO, TETRAHEDRON LETT., 31,(1990) N4, C. 6385-6386

  摘要：

  DOI：

文献信息

• Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
  作者：Tatsuya Shono、Jun Terauchi、Kenji Kitayama、Yo-ichiro Takeshima、Yoshihiro Masumura

  DOI：10.1016/s0040-4020(01)80493-2

  日期：——

  Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.

  当在含有Et 4 NOTs作为支持电解质的非质子传递溶剂（DMF或MeCN）中将Zn用作阴极材料时，腈的电还原得到相应的脱氰产物。通过使胺在α位氰化，然后将所得的α-氨基腈进行α-烷基化，然后进行电还原脱氰作用，可以有效地实现α-位胺的烷基化。
• A New Method for Introducing Some Active Methylene or Methine Groups to the 3-Position of Pyrrolidine or Piperidine Skeleton, and Its Application to Preparation of a Key Intermediate for (±)-Eburnamonine Synthesis
  作者：Tatsuya Shono、Yoshihiro Matsumura、Masaru Ogaki、Osamu Onomura

  DOI：10.1246/cl.1987.1447

  日期：1987.7.5

  A new method for introducing a bis(methoxycarbonyl)methyl or 2-oxopropyl group to the 3-position of pyrrolidine or piperidine skeleton has been exploited, and this method could be used in the synthesis of a key intermediate for the (±)-eburnamonine synthesis.

  开发了一种在吡咯烷或哌啶骨架的3-位引入双(甲氧基羰基)甲基或2-氧代丙基的新方法，该方法可用于合成(±)-乙丙氨酮的关键中间体合成。
• A convenient route to β-aryl-substituted cyclic enamines as key synthetic intermediates of sceletium and amaryllidaceae alkaloids
  作者：Yoshihiro Matsumura、Jun Terauchi、Takashi Yamamoto、Takashi Konno、Tatsuya Shono

  DOI：10.1016/s0040-4020(01)96258-1

  日期：1993.9

  Aryl groups were introduced into the position β to the nitrogen atom of cyclic amines by carrying out the anodic α-methoxylation of cyclic amine derivatives, the elimination of methanol from the oxidized products, the halomethoxylation of the resulting α,β-unsaturated cyclic amine derivatives, the replacement of the α-methoxy group with an aryl group, and the silver ion-promoted migration of the α-aryl

  通过进行环胺衍生物的阳极α-甲氧基化，从氧化产物中除去甲醇，所得α，β-不饱和环胺衍生物的卤代甲氧基化，将芳基引入到环胺氮原子的β位。 ，用芳基取代α-甲氧基，以及银离子促进α-芳基向β位置的迁移。该方法被用于一些生物碱的合成，如（±）-中间膜。
• A Convenient Method for Synthesis of Optically Active Methylphenidate from N-Methoxycarbonylpiperidine by Utilizing Electrochemical Oxidation and Evans Aldol-type Reaction
  作者：Yoshihiro Matsumura、Yasuhisa Kanda、Kimihiro Shirai、Osamu Onomura、Toshihide Maki

  DOI：10.1016/s0040-4020(00)00653-0

  日期：2000.9

  A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding alpha-methoxylated carbamate utilizing electrochemical oxidation followed by the coupling reaction with optically active Evans imides to produce optically active methylphenidate derivatives with high stereoselectivity (erythrolthreo=5.3/94.7, the three isomer; 99.6%ee). (C) 2000 Elsevier Science 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