C-((2S,3S)-3-Methyl-oxiranyl)-methylamine | 144406-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: C-((2S,3S)-3-Methyl-oxiranyl)-methylamine
• 英文别名: [(2S,3S)-3-methyloxiran-2-yl]methanamine
• CAS: 144406-02-0
• 化学式: C₄H₉NO
• 分子量: 87.1216
• InChiKey: DQFJZBVPOLGQMB-IMJSIDKUSA-N

物化性质

• 沸点：
  115.1±13.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  C-((2S,3S)-3-Methyl-oxiranyl)-methylamine 生成 (S)-(S)-1-Aziridin-2-yl-ethanol
  参考文献：
  名称：

  Rearrangement of primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols.

  摘要：

  Conditions were found to transform primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols which involve an intramolecular opening of the epoxide ring mediated by trimethylaluminum.

  DOI：

  10.1016/s0040-4039(00)79090-3
• 作为产物：
  描述：

  trans-C-(3-methyloxiranyl)methylazide 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到C-((2S,3S)-3-Methyl-oxiranyl)-methylamine
  参考文献：
  名称：

  Rearrangement of primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols.

  摘要：

  Conditions were found to transform primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols which involve an intramolecular opening of the epoxide ring mediated by trimethylaluminum.

  DOI：

  10.1016/s0040-4039(00)79090-3

文献信息

• Aza-Payne Rearrangement of Activated 2-Aziridinemethanols and 2,3-Epoxy Amines under Basic Conditions
  作者：Toshiro Ibuka、Kazuo Nakai、Hiromu Habashita、Yuka Hotta、Akira Otaka、Hirokazu Tamamura、Nobutaka Fujii、Norio Mimura、Yoshihisa Miwa、Yukiyasu Chounan、Yoshinori Yamamoto

  DOI：10.1021/jo00112a028

  日期：1995.4

  An aza-Payne rearrangement of activated 2-aziridinemethanols with t-BuOK, NaH, or KH at near 0 degrees C in common solvents such as THF, toluene, 1,2-dimethoxyethane, 1,4-dioxane, or a mixed solvent of THF-HMPA followed by quenching at -78 degrees C gives the corresponding epoxysulfonamides. Exposure of N-tosyl-(2S)-azetidinemethanol (36) and N-tosyl-(S)-prolinol (37) to NaH or KH in dichloromethane yielded only the respective dimeric compounds that resulted by joining 2 equiv of reactant through a methylene group. Reaction of N-tosyl-(2S,3S)-3-methyl-2-aziridinemethanol (9) and its (2R,3S)-isomer 23 with Gilman reagents (R(2)CuLi; R = Me and Bu) or ''higher order'' cuprates [R(2)Cu(CN)Li-2; R = Me and Bu] yielded the two expected aziridine ring-opening products. In sharp contrast, treatment of 9 and 23 with ''lower order'' cuprates afforded rearrangement-opened products. Thus, if the nucleophile is highly reactive, then the expected nucleophilic ring opening of the aziridine predominates. However, if the nucleophile is less reactive, then it becomes possible to cleave the resulting rearranged epoxide. Upon exposure of 2,3-epoxy amines to an equimolar mixture of t-BuOK-n-BuLi in a mixed solvent of THF and n-hexane at -78 degrees C, the equilibrium lies exclusively toward the hydroxy aziridine forming direction.