(2S,3S)-3-hydroxymethylaziridine-2-carboxylic acid ethyl ester | 1021177-31-0

• 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: (2S,3S)-3-hydroxymethylaziridine-2-carboxylic acid ethyl ester
• 英文别名: (S,S)-3-hydroxymethylaziridine-2-carboxylic acid ethyl ester；(2S,3S)-ethyl 3-(hydroxymethyl)aziridine-2-carboxylate；(S,S) 3-hydroxymethylaziridine-2-carboxylic acid ethyl ester；ethyl (2S,3S)-3-(hydroxymethyl)aziridine-2-carboxylate
• CAS: 1021177-31-0
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: AVOLZWQNUOCGGJ-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxymethylaziridine-2-carboxylic acid ethyl ester 在 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 6-(tert-butyldimethylsilanyloxymethyl)-2-[3-(tert-butyldimethylsilanyloxymethyl)-aziridin-2-yl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
  参考文献：
  名称：

  Readily Available Unprotected Amino Aldehydes

  摘要：

  We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a high barrier imposed on this process by the aziridine ring strain. The resulting amino aldehydes exist as dimers and in the solid state. They are stable to epimerization and contain two orthogonal reaction centers, namely, an amine/aziridine and an aldehyde. Their ability to act as linchpins has been evaluated in complex heterocycle synthesis. For instance, pentacyclic frameworks can be made in one simple operation using N-benzyltryptamine as the reaction partner. Construction of other molecular skeletons with minimal use of protecting group manipulations should be feasible.

  DOI：

  10.1021/ja065898s
• 作为产物：
  描述：

  L-(+)-酒石酸二乙酯 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 27.75h， 生成 (2S,3S)-3-hydroxymethylaziridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Readily Available Unprotected Amino Aldehydes

  摘要：

  We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a high barrier imposed on this process by the aziridine ring strain. The resulting amino aldehydes exist as dimers and in the solid state. They are stable to epimerization and contain two orthogonal reaction centers, namely, an amine/aziridine and an aldehyde. Their ability to act as linchpins has been evaluated in complex heterocycle synthesis. For instance, pentacyclic frameworks can be made in one simple operation using N-benzyltryptamine as the reaction partner. Construction of other molecular skeletons with minimal use of protecting group manipulations should be feasible.

  DOI：

  10.1021/ja065898s

文献信息

• Aziridine aldehydes, aziridine-conjugated amino derivatives, aziridine-conjugated biomolecules and processes for their preparation
  申请人：The Governing Council of the University of Toronto

  公开号：US08143375B2

  公开（公告）日：2012-03-27

  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.

  本发明涉及未保护的氨基醛及其应用。更具体地说，本发明涉及新型环氧丙烷醛和制备这些新化合物的过程。本发明还涉及环氧丙烷醛偶联的氨基衍生物以及制备它们的过程。可以使用本发明的环氧丙烷醛制备五环化合物，本发明涉及这些化合物以及制备它们的过程。本发明还涉及环氧丙烷醛偶联的生物活性分子，例如氨基酸和肽，以及制备这些化合物的过程。
• AZIRIDINE ALDEHYDES, AZIRIDINE-CONJUGATED AMINO DERIVATIVES, AZIRIDINE-CONJUGATED BIOMOLECULES AND PROCESSES FOR THEIR PREPARATION
  申请人：Yudin Andrei K.

  公开号：US20100317832A1

  公开（公告）日：2010-12-16

  The present invention 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.

  本发明适用于同类领域。更具体地说，本发明涉及新型环氧丙烷醛和制备这些新化合物的方法。本发明还涉及环氧丙烷醛偶联的氨基衍生物以及制备它们的方法。可以使用本发明的环氧丙烷醛制备五环化合物，并且本发明涉及这些化合物以及制备它们的方法。本发明还涉及环氧丙烷醛偶联的生物活性分子，例如氨基酸和肽，以及制备这些化合物的方法。
• WO2008/46232
  申请人：——

  公开号：——

  公开（公告）日：——
• Amphoteric Amino Aldehydes Enable Rapid Assembly of Unprotected Amino Alcohols
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1002/anie.200705776

  日期：2008.5.19
• Hili, Ryan; Rai, Vishal; Yudin, Andrei K., Journal of the American Chemical Society, 2010, vol. 132, p. 2889 - 2891
  作者：Hili, Ryan、Rai, Vishal、Yudin, Andrei K.

  DOI：——

  日期：——