3-(1-adamantyl)-1-triphenylmethylaziridin-2-one | 431946-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-(1-adamantyl)-1-triphenylmethylaziridin-2-one
• 英文别名: 3-(1-adamantyl)-1-triphenylmethylaziridinone；3-(1-Adamantyl)-1-tritylaziridin-2-one
• CAS: 431946-21-3
• 化学式: C₃₁H₃₁NO
• 分子量: 433.593
• InChiKey: JIYKYDWKQULBIF-UHFFFAOYSA-N

物化性质

• 沸点：
  573.2±60.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-(1-adamantyl)-1-triphenylmethylaziridin-2-one 反应 24.0h， 以89.4%的产率得到N-triphenylmethyl-2-(1-adamantyl)-2-methoxyacetamide
  参考文献：
  名称：

  About Four New Trityl-substituted a-Lactams

  摘要：

  This investigation comprises the synthesis, a description of the physical and spectroscopic properties, determination of the limits of thermal stability, and reactions with protic and aprotic nucleophiles of four new trityl-substituted alpha-lactams. With the exception of 3,3-dimethyl-1-tritylaziridin-2-one (4a), which is unstable at room temperature, all new compounds have been fully characterized.

  DOI：

  10.3987/com-01-9365
• 作为产物：
  描述：

  N-triphenylmethyl-2-bromoadamantanacetamide 在 sodium t-butanolate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以74%的产率得到3-(1-adamantyl)-1-triphenylmethylaziridin-2-one
  参考文献：
  名称：

  About Four New Trityl-substituted a-Lactams

  摘要：

  This investigation comprises the synthesis, a description of the physical and spectroscopic properties, determination of the limits of thermal stability, and reactions with protic and aprotic nucleophiles of four new trityl-substituted alpha-lactams. With the exception of 3,3-dimethyl-1-tritylaziridin-2-one (4a), which is unstable at room temperature, all new compounds have been fully characterized.

  DOI：

  10.3987/com-01-9365

文献信息

• About the Factors Which Govern the Ring-opening of a-Lactams with Benzylamine I. The Relative Stability of the a-Lactam and the Substituent on Nitrogen
  作者：István Lengyel、Victor Cesare、Sihao Chen、Tony Taldone

  DOI：10.3987/com-02-9453

  日期：——

  Eight α-lactams (aziridinones) of varying stability, one of them previously unreported, were synthesized and reacted with benzylamine. Three of the α-lactams, 1-(1-adamantyl)-3,3-dimethylaziridinone (2j), 3,3-dimethyl-1-triphenylmethylaziridinone (2m), and 3-phenyl-1-triphenylmethyl-aziridinone (20) gave α-benzylaminoamides (3j, 3m, 3o) as products, indicating C 3 -N bond cleavage. Four α-lactams, 1,

  合成了八种不同稳定性的α-内酰胺（氮丙啶酮），其中一种以前未报道过，并与苄胺反应。三种 α-内酰胺，1-(1-金刚烷基)-3,3-二甲基氮丙啶酮 (2j)、3,3-二甲基-1-三苯基甲基氮丙啶酮 (2m) 和 3-苯基-1-三苯基甲基-氮丙啶酮 (20)得到α-苄基氨基酰胺（3j，3m，3o）作为产物，表明C 3 -N键断裂。四种 α-内酰胺、1,3-二叔丁基氮丙啶酮 (2g)、1-叔丁基-3-三苯基甲基氮丙啶酮 (2i)、1-(1-金刚烷基)-3-叔丁基氮丙啶酮 (2k) 和 I -(I-金刚烷基)-3-三苯基甲基氮丙啶酮 (2l) 产生 N-苄基酰胺 (4g, 4i, 4k, 4l)，由 C 2 -N 键断裂产生。3-(1-金刚烷基)-1-三苯基甲基氮丙啶酮 (2n) 得到两种加合物 (3n, 4n) 的混合物。基于这些实验结果，
• About the Factors Which Govern the Ring-Opening of a-Lactams with Primary Amines: II. The Relative Basicity of the Amine
  作者：Victor Cesare、Tony Taldone、István Lengyel

  DOI：10.3987/com-02-9585

  日期：——

  3-tert-butyl-1-triphenylmethylaziridinone (1e), and 1-(1-adamantyl)-3-tert-butylaziridinone (1g) with some substituted benzylamines and other selected primary amines is described. It emerges from the experimental results that the relative basicity of the amine is a decisive factor in determining regioselectivity in the ring-opening.

  四种稳定的 α-内酰胺的开环反应，1-(1-金刚烷基)-3,3-二甲基氮丙啶酮 (1a), 3-(1-金刚烷基)-1-三苯基甲基-氮丙啶酮 (1d), 3-描述了叔丁基-1-三苯基甲基氮丙啶酮 (1e) 和 1-(1-金刚烷基)-3-叔丁基氮丙啶酮 (1g) 以及一些取代的苄胺和其他选定的伯胺。从实验结果可以看出，胺的相对碱性是决定开环区域选择性的决定性因素。