(R)-1-Trityl-aziridine-2-carboxylic acid benzyl ester | 126496-78-4

• 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: (R)-1-Trityl-aziridine-2-carboxylic acid benzyl ester
• 英文别名: benzyl (2R)-1-tritylaziridine-2-carboxylate
• CAS: 126496-78-4
• 化学式: C₂₉H₂₅NO₂
• 分子量: 419.523
• InChiKey: QGOFOWMHAYEUGY-NHQUYOMTSA-N

物化性质

• 沸点：
  521.8±50.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-Trityl-aziridine-2-carboxylic acid benzyl ester 在 zinc trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 18.0h， 生成 Z-D-色氨酸苄酯
  参考文献：
  名称：

  Construction of optically pure tryptophans from serine derived aziridine-2-carboxylates

  摘要：

  DOI：

  10.1016/s0040-4039(00)99325-0
• 作为产物：
  描述：

  N-三苯甲基-D-丝氨酸-甲酯 在 甲基磺酰氯 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 75.5h， 生成 (R)-1-Trityl-aziridine-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  10.17344/acsi.2022.6673

  摘要：

  DOI：

  10.17344/acsi.2022.6673

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.
• SATO, K.;KOZIKOWSKI, ALAN P., TETRAHEDRON LETT., 30,(1989) N1, C. 4073-4076
  作者：SATO, K.、KOZIKOWSKI, ALAN P.

  DOI：——

  日期：——
• Construction of optically pure tryptophans from serine derived aziridine-2-carboxylates
  作者：Kazuo Sato、Alan P. Kozikowski

  DOI：10.1016/s0040-4039(00)99325-0

  日期：1989.1
• 10.17344/acsi.2022.6673
  作者：Kuzmič, Samo、Hrast, Martina、Frlan, Rok

  DOI：10.17344/acsi.2022.6673

  日期：——