methyl 2-methyl-1-aziridinecarboxylate | 109334-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丙烷
• 英文名称: methyl 2-methyl-1-aziridinecarboxylate
• 英文别名: N-Methoxycarbonyl-2-methylaziridine；Methyl 2-methylaziridine-1-carboxylate
• CAS: 109334-12-5
• 化学式: C₅H₉NO₂
• 分子量: 115.132
• InChiKey: USFAMHJUWLPPLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-1-aziridinecarboxylate 、 苯甲醛 在 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以17%的产率得到((E)-1-Methyl-3-phenyl-allyl)-carbamic acid methyl ester
  参考文献：
  名称：

  在不存在外源性碱的情况下进行的Wittig烯化：α-取代的伯烯丙基胺的新合​​成。

  摘要：

  据报道，通过N-酰基氮丙啶，三苯基膦和醛在回流的异丙醇中的反应原位生成和捕获内酰胺，可以合成α-取代的伯烯丙基胺。通过使用手性非外消旋N-酰基氮丙啶，可以对映选择性地制备这些化合物（> 94.6％ee）。

  DOI：

  10.1016/s0040-4039(00)94666-5
• 作为产物：
  描述：

  氯甲酸甲酯 、 2-甲基氮丙啶 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以85%的产率得到methyl 2-methyl-1-aziridinecarboxylate
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 1a-formyl and 1a-thioformyl derivatives of mitomycin C and 2-methylaziridine

  摘要：

  A select number of 1-formyl- and 1-thioformyl-2-methylaziridine derivatives and the corresponding 1a-substituted mitomycin C analogues were synthesized and tested for antineoplastic activity by using an in vivo test with murine P388 leukemia. Select compounds were also tested in vivo with murine melanoma B16. Several of the mitomycin C derivatives displayed activity and some of the mitomycin C analogues were comparable in activity to the parent compound.

  DOI：

  10.1021/jm00393a015

文献信息

• FISHBEIN, PAUL L.;KOHN, HAROLD, J. MED. CHEM., 30,(1987) N 10, 1767-1773
  作者：FISHBEIN, PAUL L.、KOHN, HAROLD

  DOI：——

  日期：——
• Synthesis and antineoplastic activity of 1a-formyl and 1a-thioformyl derivatives of mitomycin C and 2-methylaziridine
  作者：Paul L. Fishbein、Harold Kohn

  DOI：10.1021/jm00393a015

  日期：1987.10

  A select number of 1-formyl- and 1-thioformyl-2-methylaziridine derivatives and the corresponding 1a-substituted mitomycin C analogues were synthesized and tested for antineoplastic activity by using an in vivo test with murine P388 leukemia. Select compounds were also tested in vivo with murine melanoma B16. Several of the mitomycin C derivatives displayed activity and some of the mitomycin C analogues were comparable in activity to the parent compound.
• Wittig olefination in the absence of an exogenous base: A new synthesis of α-substituted primary allylic amines.
  作者：Joseph F. Dellaria、Kevin J. Sallin

  DOI：10.1016/s0040-4039(00)94666-5

  日期：1990.1

  A new synthesis of α-substituted primary allylic amines through the in situ generation and trapping of an ylide from the reaction of an N-acyl aziridine, triphenylphosphine, and an aldehyde in refluxing isopropanol is reported. These compounds can be prepared enantioselectively (>94.6% ee) by employing a chiral nonracemic N-acyl aziridine.

  据报道，通过N-酰基氮丙啶，三苯基膦和醛在回流的异丙醇中的反应原位生成和捕获内酰胺，可以合成α-取代的伯烯丙基胺。通过使用手性非外消旋N-酰基氮丙啶，可以对映选择性地制备这些化合物（> 94.6％ee）。