2-aziridin-2-yl-3-oxa-1-aza-bicyclo[3.1.0]hexan-4-ol | 1000072-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-aziridin-2-yl-3-oxa-1-aza-bicyclo[3.1.0]hexan-4-ol
• 英文别名: (2S,4S,5R)-2-[(2R)-aziridin-2-yl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
• CAS: 1000072-77-4
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: WLKQLTSLRNRVSR-OEGLBHDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-phenylalanine allyl ester 、 异氰酸叔丁酯 、 2-aziridin-2-yl-3-oxa-1-aza-bicyclo[3.1.0]hexan-4-ol 、 苯硫酚 在 三乙酰氧基硼氢化钠 、 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 4.0h， 以36%的产率得到(2R,3S,6R)-6-benzyl-N-tert-butyl-5-oxo-3-[(phenylsulfanyl)methyl]piperazine-2-carboxamide trifluoroacetate
  参考文献：
  名称：

  Solid-Phase Synthesis of Piperazinones via Disrupted Ugi Condensation

  摘要：

  The first application of aziridine aldehyde dimers in solid-phase synthesis is reported. The solid-supported disrupted Ugi condensation between an aziridine aldehyde dimer, isonitrile, and backbone-anchored amino acids delivered N-acyl aziridine intermediates, which were reacted with nucleophiles to yield the corresponding piperazinones. Subsequent cleavage from the resin provided a diverse set of 2,3,6-trisubstituted piperazinones starting from various amino acids, aziridine aldehydes, and nucleophiles.

  DOI：

  10.1021/ol5023118
• 作为产物：
  描述：

  (R)-propyl aziridine-2-carboxylate 在 二异丁基氢化铝 、 甲醇 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以57%的产率得到2-aziridin-2-yl-3-oxa-1-aza-bicyclo[3.1.0]hexan-4-ol
  参考文献：
  名称：

  WO2008/46232

  摘要：

  公开号：

文献信息

• Solid-Phase Parallel Synthesis of Functionalised Medium-to-Large Cyclic Peptidomimetics through Three-Component Coupling Driven by Aziridine Aldehyde Dimers
  作者：Adam P. Treder、Jennifer L. Hickey、Marie-Claude J. Tremblay、Serge Zaretsky、Conor C. G. Scully、John Mancuso、Annie Doucet、Andrei K. Yudin、Eric Marsault

  DOI：10.1002/chem.201500068

  日期：2015.6.15

  solid‐phase parallel synthesis of macrocyclic peptides using three‐component coupling driven by aziridine aldehyde dimers is described. The method supports the synthesis of 9‐ to 18‐membered aziridine‐containing macrocycles, which are then functionalized by nucleophilic opening of the aziridine ring. This constitutes a robust approach for the rapid parallel synthesis of macrocyclic peptides.

  描述了使用氮丙啶醛二聚体驱动的三组分偶联的大环肽的首次固相平行合成。该方法支持合成9至18元含氮丙啶的大环，然后通过氮丙啶环的亲核开环将其官能化。这构成了快速并行合成大环肽的可靠方法。
• [EN] AZIRIDINE ALDEHYDES, AZIRIDINE-CONJUGATED AMMO DERIVATIVES, AZIRIDINE-CONJUGATED BIOMOLECULES AND PROCESSES FOR THEIR PREPARATION<br/>[FR] ALDÉHYDES AZIRIDINE, DÉRIVÉS AMINÉS À CONJUGAISON AZIRIDINE, BIOMOLÉCULES À CONJUGAISON AZIRIDINE ET PROCÉDÉS POUR LES PRÉPARER
  申请人：YUDIN ANDREI K

  公开号：WO2008046232A1

  公开（公告）日：2008-04-24

  [EN] The present invention relates to unprotected amino aldehydes and applications for same. More particularly, the present invention relates to novel aziridine aldehydes and processes for preparing these novel compounds. The invention also relates to aziridine-conjugated amino derivatives, and processes for preparing the same. Pentacyclic compounds may be prepared using the aziridine aldehydes of the present invention, and the invention relates to these compounds and the processes by which they are made. The invention also relates to aziridine-conjugated bioactive molecules, such as amino acids and peptides, and processes for preparing such compounds.
  [FR] La présente invention concerne des aldéhydes aminés non protégés et leurs applications. L'invention concerne plus particulièrement de nouveaux aldéhydes aziridine ainsi que des procédés pour les préparer. L'invention concerne également des dérivés aminés à conjugaison Aziridine, ainsi que des procédés pour les préparer. Il est possible de préparer des composés pentacycliques à partir des aldéhydes aziridine de la présente invention, laquelle concerne également lesdits composés pentacycliques et les procédés permettant de les préparer. L'invention concerne en outre des molécules bioactives à conjugaison aziridine, par exemple des acides aminés et des peptides, ainsi que des procédés pour les préparer.
• WO2008/46232
  申请人：——

  公开号：——

  公开（公告）日：——
• Solid-Phase Synthesis of Piperazinones via Disrupted Ugi Condensation
  作者：Adam P. Treder、Marie-Claude Tremblay、Andrei K. Yudin、Eric Marsault

  DOI：10.1021/ol5023118

  日期：2014.9.5

  The first application of aziridine aldehyde dimers in solid-phase synthesis is reported. The solid-supported disrupted Ugi condensation between an aziridine aldehyde dimer, isonitrile, and backbone-anchored amino acids delivered N-acyl aziridine intermediates, which were reacted with nucleophiles to yield the corresponding piperazinones. Subsequent cleavage from the resin provided a diverse set of 2,3,6-trisubstituted piperazinones starting from various amino acids, aziridine aldehydes, and nucleophiles.