1-(p-nosyl)aziridine-2R-carboxylic acid methyl ester | 1021495-51-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(p-nosyl)aziridine-2R-carboxylic acid methyl ester
• 英文别名: methyl (2R)-1-(4-nitrophenyl)sulfonylaziridine-2-carboxylate
• CAS: 1021495-51-1
• 化学式: C₁₀H₁₀N₂O₆S
• 分子量: 286.265
• InChiKey: TXTJASSWOJIKFC-BFHBGLAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-(p-nosyl)aziridine-2R-carboxylic acid methyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以81 %的产率得到
  参考文献：
  名称：

  CN115260128

  摘要：

  公开号：
• 作为产物：
  描述：

  对硝基苯磺酰氯 、 (r)-1-三苯甲游基-2-氮丙啶羧酸甲酯 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 24.67h， 生成 1-(p-nosyl)aziridine-2R-carboxylic acid methyl ester
  参考文献：
  名称：

  Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

  摘要：

  Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding beta-methyl azalanthionines have, so far, been unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.011

文献信息

• Microwave-Assisted Ring-Opening of Activated Aziridines with Resin-Bound Amines
  作者：François Crestey、Matthias Witt、Karla Frydenvang、Dan Stærk、Jerzy W. Jaroszewski、Henrik Franzyk

  DOI：10.1021/jo702612u

  日期：2008.5.1

  nosylamide-activated aziridines under microwave irradiation conditions in solid-phase synthesis (SPS). The effects of solvent, temperature, reaction time, and reagent ratio in SPS of partially protected triamines from aziridines and resin-bound diamines were investigated. The methodology was also optimized for the synthesis of novel amino acid derivatives.

  本文描述了在固相合成（SPS）中在微波辐射条件下，由Nosylamide活化的氮丙啶进行亲核开环的第一个研究。研究了溶剂，温度，反应时间和试剂比率对部分保护的三胺与氮丙啶和树脂结合的二胺的SPS的影响。还对该方法进行了优化，以合成新的氨基酸衍生物。
• Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates
  作者：Keith O’Brien、Keith ó Proinsias、Fintan Kelleher

  DOI：10.1016/j.tetlet.2013.02.096

  日期：2013.5

  Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or beta-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs). The required DAPs were also synthesised by ring-opening of N-protected aziridine 2-carboxylates with para-methoxybenzylamine. (C) 2013 Elsevier Ltd. All rights reserved.