(4R,5S)-1,5-dimethyl-3-[(2S,3R)-3-methylaziridine-2-carbonyl]-4-phenylimidazolidin-2-one | 183074-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-1,5-dimethyl-3-[(2S,3R)-3-methylaziridine-2-carbonyl]-4-phenylimidazolidin-2-one
• CAS: 183074-26-2
• 化学式: C₁₅H₁₉N₃O₂
• 分子量: 273.335
• InChiKey: FGYJWSNDJJIDAC-URBCHYCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-1,5-dimethyl-3-[(2S,3R)-3-methylaziridine-2-carbonyl]-4-phenylimidazolidin-2-one 在 三氟化硼乙醚 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 {(S)-1-[(1S,2R)-1-((4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-imidazolidine-1-carbonyl)-2-hydroxy-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of optically pure threonine-containing dipeptides by regio- and stereo-controlled ring expansion of aziridine-2-imide derivatives

  摘要：

  本文描述了手性N-(α-氨基酰基)氮丙啶-2-亚胺向恶唑啉的环-和立体选择性环扩张，以及随后向具有所需立体化学结构的光学纯的含苏氨酸二肽的环开放。

  DOI：

  10.1039/a807063f
• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenyl-3-[(3R)-3-(phenylmethoxyamino)butanoyl]imidazolidin-2-one 在 四氯化钛 、 三乙胺 作用下， 生成 (4R,5S)-1,5-dimethyl-3-[(2S,3R)-3-methylaziridine-2-carbonyl]-4-phenylimidazolidin-2-one
  参考文献：
  名称：

  Cardillo, Giuliana; Casolari, Sonia; Gentilucci, Luca, Angewandte Chemie, 1996, vol. 108, # 16, p. 1939 - 1941

  摘要：

  DOI：

文献信息

• Synthesis of Enantiomerically Pure Aziridine-2-imides by Cyclization of Chiral 3‘-Benzyloxyamino Imide Enolates
  作者：Alessandro Bongini、Giuliana Cardillo、Luca Gentilucci、Claudia Tomasini

  DOI：10.1021/jo971254e

  日期：1997.12.1

  Aziridine-2-imides are prepared both in high yield and high diastereoselectivity from chiral 3'-benzyloxyamino imides 2, 3, and 8 by treatment with triethylamine in the presence of either TiCl4 or AlMe2Cl. 2 and 3 are easily obtained by a diastereoselective conjugate addition of O-benzylhydroxylamine promoted by Lewis acids to alpha,beta-unsaturated imides 1. The synthesis of 3'-(benzyloxyamino)propanoyl 8 is performed by addition to the acryloyl compound 6 of N-BOC O-benzylhydroxylamine followed by deprotection. The cyclization of 2 and 3 affords complete trans selectivity and yields up to 97% of the corresponding 3'-alkyl aziridines 4 and 5, while the cyclization of 8 affords a mixture of diasteroisomers 11, 12 in 86/14 ratio and a 95% yield. A mechanistic study has been made to rationalize the trans selectivity observed in the cyclization of 2 and 3. AM1 computations allow us to deduce that the reaction proceeds through cyclic titanium or aluminum enolate formation, and they reveal that enolates leading to trans aziridines are more stable than those leading to cis.
• A New Selective Synthesis of the Ile-<i>a</i><i>llo</i>-Thr-Gly Tripeptide Fragment of Lysobactin
  作者：Silvia Armaroli、Giuliana Cardillo、Luca Gentilucci、Massimo Gianotti、Alessandra Tolomelli

  DOI：10.1021/ol005659o

  日期：2000.4.1

  trans-Aziridine-2-carboxylic acid derivatives are useful intermediates for the synthesis of threonine or allo-threonine through ring expansion and S(N)2 displacement, respectively. We describe here the preparation of the Ile-allo-Thr-Gly 11 fragment of Lysobactin via the aziridine 9 intermediate.