1-methyl-trans-2,3-diphenylaziridine | 104156-51-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-methyl-trans-2,3-diphenylaziridine
• 英文别名: trans-1-methyl-2,3-diphenylaziridine；(2S,3S)-1-methyl-2,3-diphenylaziridine
• CAS: 104156-51-6
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: WLBLGOSZSFSCLD-GJZGRUSLSA-N

物化性质

• 沸点：
  120-125 °C(Press: 0.25 Torr)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二苯基甲烷硫酮 、 1-methyl-trans-2,3-diphenylaziridine 以 甲苯 为溶剂， 反应 0.75h， 以66%的产率得到cis-3-methyl-2,4,5,5-tetraphenyl-1,3-thiazolidine
  参考文献：
  名称：

  反式-1-甲基-2-3,2-二苯基氮丙啶与CS和CC双极性亲热剂的[2 + 3]-环热加成反应：富马酸二甲酯的意外反应

  摘要：

  的热反应的反式-1-甲基-2,3- diphenylaziridine（反式- 1A与芳族和脂环族硫酮）2在沸腾的甲苯，得到相应的顺式-2,4-二苯基-1,3-噻唑烷的顺式- 4 经由conrotatory的开环反式- 1A和中间的一致[2 + 3] -环（ê，ê）构型的偶氮甲碱内鎓盐3a中（方案1）。cis ‐ 1a与乙炔二甲酸二甲酯的类似反应（5），得到二甲基反式-2,5-二氢-1-甲基-2,5-二苯基吡咯-3,4-二羧酸二乙酯（反式- 6与轨道对称控制的反应一致）（方案2）。在另一方面，的反应顺式- 1A和反式- 1A与二甲dicyanofumarate（图7a），以及其的顺式- 1A和二甲基dicyanomaleate（图7b），导致了同样的两种立体异构二甲酯的混合物3,4-二氰基-1-甲基-2,5-二苯基吡咯烷-3,4-二羧酸酯8a和8b（方案3）。该结果必须通过逐步反应机理来解

  DOI：

  10.1002/hlca.200900236
• 作为产物：
  描述：

  Stilbene oxide 在 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 1-methyl-trans-2,3-diphenylaziridine
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)

  摘要：

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.

  DOI：

  10.1021/jm00161a019

文献信息

• Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)
  作者：Wayne K. Anderson、Arnold S. Milowsky

  DOI：10.1021/jm00161a019

  日期：1986.11

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.
• Thermal [2+3]-Cycloadditions of trans-1-Methyl-2,3-diphenylaziridine with CS and CC Dipolarophiles: An Unexpected Course with Dimethyl Dicyanofumarate
  作者：Grzegorz Mlostoń、Katarzyna Urbaniak、Małgorzata Domagała、Arno Pfitzner、Manfred Zabel、Heinz Heimgartner

  DOI：10.1002/hlca.200900236

  日期：2009.12

  orbital‐symmetry‐controlled reactions (Scheme 2). On the other hand, the reactions of cis‐1a and trans‐1a with dimethyl dicyanofumarate (7a), as well as that of cis‐1a and dimethyl dicyanomaleate (7b), led to mixtures of the same two stereoisomeric dimethyl 3,4‐dicyano‐1‐methyl‐2,5‐diphenylpyrrolidine‐3,4‐dicarboxylates 8a and 8b (Scheme 3). This result has to be explained via a stepwise reaction mechanism, in which

  的热反应的反式-1-甲基-2,3- diphenylaziridine（反式- 1A与芳族和脂环族硫酮）2在沸腾的甲苯，得到相应的顺式-2,4-二苯基-1,3-噻唑烷的顺式- 4 经由conrotatory的开环反式- 1A和中间的一致[2 + 3] -环（ê，ê）构型的偶氮甲碱内鎓盐3a中（方案1）。cis ‐ 1a与乙炔二甲酸二甲酯的类似反应（5），得到二甲基反式-2,5-二氢-1-甲基-2,5-二苯基吡咯-3,4-二羧酸二乙酯（反式- 6与轨道对称控制的反应一致）（方案2）。在另一方面，的反应顺式- 1A和反式- 1A与二甲dicyanofumarate（图7a），以及其的顺式- 1A和二甲基dicyanomaleate（图7b），导致了同样的两种立体异构二甲酯的混合物3,4-二氰基-1-甲基-2,5-二苯基吡咯烷-3,4-二羧酸酯8a和8b（方案3）。该结果必须通过逐步反应机理来解