1-Carbomethoxy-2-methoxy-hexamethylenimine | 84839-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 1-Carbomethoxy-2-methoxy-hexamethylenimine
• 英文别名: methyl 2-methoxyazepane-1-carboxylate
• CAS: 84839-66-7
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: PJLLUBKXXQSUPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  1-Carbomethoxy-2-methoxy-hexamethylenimine 在 氯化铵 作用下， 生成 N-(甲氧羰基)氮杂-2-环庚烯
  参考文献：
  名称：

  Ring Contraction of α,β-Unsaturated Cyclic Amines with cis-Dihydroxylation at the α,β-Position

  摘要：

  alpha,beta-Unsaturated cyclic amines are oxidized by OsO(4) to afford alpha,beta-cis-dihydroxylated compounds which are thermodynamically transformed into ring-opened keto-alcohols. The keto-alcohols are then cyclized to form synthetically useful ring-contracted cyclic amines.

  DOI：

  10.3987/com-08-s(f)18
• 作为产物：
  描述：

  N-methoxycarbonylhexamethyleneimine 以 甲醇 为溶剂， 以89%的产率得到1-Carbomethoxy-2-methoxy-hexamethylenimine
  参考文献：
  名称：

  Electroorganic chemistry. 82. .beta.-Amino acid esters from .alpha.-methoxycarbamates and ketene silyl acetals; cyclization to .beta.-lactams

  摘要：

  DOI：

  10.1021/jo00180a020

文献信息

• Electrochemical Deallylation of α-Allyl Cyclic Amines and Synthesis of Optically Active Quaternary Cyclic Amino Acids
  作者：Peter G. Kirira、Masami Kuriyama、Osamu Onomura

  DOI：10.1002/chem.200903512

  日期：2010.4.6

  Electrochemical oxidation of α‐allylated and α‐benzylated N‐acylated cyclic amines by using a graphite anode easily affords the corresponding α‐methoxylated products with up to 76 % yield. Ease of oxidation was affected by the type of electrode, the size of cyclic amine, and the nature of the protecting group. This method was successfully applied to the synthesis of optically active N‐acylated α‐alkyl‐α‐amino

  通过使用石墨阳极对α-烯丙基化和α-苄基化N-酰化的环状胺进行电化学氧化，可以轻松获得相应的α-甲氧基化产物，收率高达76％。电极的类型，环胺的大小和保护基的性质会影响氧化的难易程度。该方法已成功应用于合成具有高达99％ee的旋光性N酰化的α-烷基-α-氨基酸酯 。
• A NEW SYNTHETIC METHOD OF 1-AZABICYCLO[4.<i>n</i>.0]SYSTEMS
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenji Tsubata、Kenji Inoue、Ryoichi Nishida

  DOI：10.1246/cl.1983.21

  日期：1983.1.5

  A new method for the synthesis of bicyclic pyridinium salts from alicyclic amines and reduction of the salts to 1-azabicyclo[4.n.0]systems has been exploited.

  已经开发了一种从脂环胺合成双环吡啶鎓盐并将盐还原为 1-氮杂双环 [4.n.0] 系统的新方法。
• A Convenient Method for Synthesis of Enantiomerically Enriched Methylphenidate from <i>N</i>-Methoxycarbonylpiperidine
  作者：Yoshihiro Matsumura、Yasuhisa Kanda、Kimihiro Shirai、Osamu Onomura、Toshihide Maki

  DOI：10.1021/ol9905046

  日期：1999.7.1

  [formula: see text] This report describes a new method to prepare optically active methylphenidate starting from piperidine. The method consists of a transformation of N-methoxycarbonylpiperidine to the corresponding alpha-methoxylated carbamate I by utilizing electrochemical oxidation followed by the coupling reaction with optically active Evans imides II to produce optically active methylphenidate

  [公式：见正文]该报告介绍了一种从哌啶开始制备旋光哌醋甲酯的新方法。该方法包括通过利用电化学氧化将N-甲氧基羰基哌啶转化为相应的α-甲氧基化氨基甲酸酯I，然后与旋光的Evans酰亚胺II偶联反应，以生产具有高立体选择性苏氨酸-（2R，2可以通过三步轻松地从III制备R'-哌醋甲酯（IV； Ar = Ph；利他林）。
• Expedient Preparation of Nazlinine and a Small Library of Indole Alkaloids Using Flow Electrochemistry as an Enabling Technology
  作者：Mikhail A. Kabeshov、Biagia Musio、Philip R. D. Murray、Duncan L. Browne、Steven V. Ley

  DOI：10.1021/ol502201d

  日期：2014.9.5

  An expedient synthesis of the indole alkaloid nazlinine is reported. Judicious choice of flow electrochemistry as an enabling technology has permitted the rapid generation of a small library of unnatural relatives of this biologically active molecule. Furthermore, by conducting the key electrochemical Shono oxidation in a flow cell, the loading of electrolyte can be significantly reduced to 20 mol

  据报道，吲哚生物碱纳兹林碱的简便合成方法。明智地选择流动电化学作为一种使能技术，可以快速生成这种生物活性分子的非天然亲戚的小型文库。此外，通过在流通池中进行关键的电化学Shono氧化，可以将电解质的负载显着降低至20 mol％，同时保持稳定，广泛适用的过程。
• 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.