methyl N-methylacetimidate | 52008-67-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: methyl N-methylacetimidate
• 英文别名: O-Methyl-N-Methylacetimidat
• CAS: 52008-67-0
• 化学式: C₄H₉NO
• 分子量: 87.1216
• InChiKey: ZVSTUQXCWRZVJO-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  6.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl N-methylacetimidate 、 环己胺 以 甲苯 为溶剂， 生成 N-cyclohexyl-N'-methyl-acetamidine
  参考文献：
  名称：

  Triazapentadienes as acaricides and insecticides

  摘要：

  描述了具有杀螨和杀虫特性的三氮杂戊二烯的制备。

  公开号：

  US04011343A1
• 作为产物：
  描述：

  (Z)-N-methyl-methoxyacetonitrilium fluorosulfonate 在 二异丙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以25%的产率得到methyl N-methylacetimidate
  参考文献：
  名称：

  Stereoselectivity of Additions to N-Methyl Acetonitrilium Fluorosulfonate

  摘要：

  Alkoxy-N-methyl-acetiminium salts were prepared by addition of CH3OH and C2H5OH to N-methyl acetonitrilium fluorosulfonate at low temperature. Analysis of the (5)J(HH) and (3)J(13)C-H coupling constants in the NMR spectra showed an anti addition with a diastereoselectivity of >9596. Deprotonation of these salts with (Z)-configuration gave the corresponding N-methyl-alkoxyacetimines with very high (E)-configuration. Upon protonation at -78 degrees C, these iminoesters gave the corresponding alkoxy-N-methyl-acetirninium salts with (E)-configuration. Computational analyses of the iminoesters and the corresponding iminium cations including the conformations give insight into the relative stability. Nitrilium salts can be used as reagents, exemplified by some esterifications between simple acids and alcohols.

  DOI：

  10.1021/jo301983s

文献信息

• Use of NOE difference spectra to determine configurations and conformations of imidate esters
  作者：David E. Gallis、Delanson R. Crist

  DOI：10.1002/mrc.1260250604

  日期：1987.6

  A new method for determining conformations and configurations of imidate esters was developed based on NOE difference spectra in CDCI3. As a test of the method, methyl N‐methylacetimidate was determined to exist in the E configuration, ap conformation, in agreement with assignments by homoallylic coupling and dipole moment data. Methyl N‐tert‐butylformimidate, for which existing methods were not suitable

  基于 CDCI3 中的 NOE 差异光谱，开发了一种确定亚胺酸酯构象和构型的新方法。作为该方法的测试，确定 N-甲基乙酰亚胺酸甲酯以 E 构型、p 构象存在，与同烯丙基耦合和偶极矩数据的分配一致。现有方法不适合的 N-叔丁基甲酰亚胺甲酯也被确定为 E-ap。研究了两种苯甲酸甲酯，即 N-甲基衍生物 2，即 E-ap，和 N-叔丁基衍生物 6，其在室温（Tc = 24°C）下表现出异常容易的 E/Z 异构化。在 ‐58 °C 时，解析光谱显示 E/Z 异构体 6 的比例为 40:60。从 NOE 数据确定 (E)-6 主要作为 ap 构象异构体存在，(Z)-6 作为 sp 构象异构体存在。这些结果，