cis 1-benzyl-3-methylaziridine-2-carboxylic acid ethyl ester

• 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: cis 1-benzyl-3-methylaziridine-2-carboxylic acid ethyl ester
• 英文别名: cis-ethyl 1-benzyl-3-methylaziridine-2-carboxylate；ethyl (2S,3S)-1-benzyl-3-methylaziridine-2-carboxylate
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: QTTGHNQPTOLCIM-RJXBTYEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  cis 1-benzyl-3-methylaziridine-2-carboxylic acid ethyl ester 在 dicobalt octacarbonyl 、 一氧化碳 作用下， 以 乙二醇二甲醚 为溶剂， 110.0 ℃ 、3.45 MPa 条件下， 反应 18.0h， 以73%的产率得到ethyl (Z)-3-(benzylamino)-2-butenoate
  参考文献：
  名称：

  Carbonylation of Silylated Hydroxymethyl Aziridines to β-Lactams

  摘要：

  Functionalized beta-lactams are synthesized by carbonylative ring expansion of silylated hydroxymethyl aziridines catalyzed by dicobalt octacarbonyl, a process that proceeds with inversion of configuration. Ring opening and elimination occurs on attempted carbonylation of aziridine carboxylates.

  DOI：

  10.1021/jo981568h
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 在 溴 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 24.0h， 生成 cis 1-benzyl-3-methylaziridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  以氮丙啶为模板：2-氮杂环丁烷酮立体定向合成的一般策略

  摘要：

  已经描述了获得各种氮丙啶-2-羧酸盐的各种途径，并且已经通过光谱法确定了这些化合物的立体化学。此外，β内酰胺类的更大的多样性通过由一般的，有效和直接的立体有择方法获得的这些azridines -2-羧酸酯的扩环。

  DOI：

  10.1002/jhet.5570430103

文献信息

• Stereospecific synthesis of 2,3-disubstituted aziridines from β-alkylamino phenylselenides
  作者：Stéphane Boivin、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4039(99)02159-0

  日期：2000.1

  Reduction of α-phenylselanyl imines derived from β-phenylselanyl α-oxoesters or PhSeCl assisted nucleophilic addition of primary amines to α,β-unsaturated esters have led to β-alkylamino phenylselenides 4, 5, 12 and 13 which were cyclised into aziridines 8, 9 and 14 after selenium activation. threo-Amino selenides led stereospecifically to cis-2,3-disubstituted aziridines. Depending on the structure

  从β-phenylselanylα-oxoesters或PhSeCl衍生α-phenylselanyl亚胺的还原辅助亲核加成伯胺与α，β不饱和酯导致β -烷基氨基phenylselenides 4，5，12和13，其被环化成氮丙啶8，硒活化后的图9和14。苏-氨基硒化物立体定向地生成顺式-2,3-二取代的氮丙啶。取决于结构，非官能化氨基硒化物19 - 20也被环化成氮丙啶21 - 22。
• Diastereoselective synthesis of aziridine esters via amino selanyl esters
  作者：Catherine Miniejew、Francis Outurquin、Xavier Pannecoucke

  DOI：10.1016/j.tet.2005.12.030

  日期：2006.3

  A synthesis of aziridine esters based on the cyclisation of amino selanyl esters induced by the selanyl group activation was developed with either the Meerwein salt or NBS. Two asymmetric approaches are proposed: the diastereoselective reductions of α-selanyl β-iminoesters derived from α-oxoesters, which lead to cis chiral aziridine esters 6 and 6′; and the diastereoselective conjugate additions of

  用Meerwein盐或NBS开发了基于由硒基活化引起的氨基硒基酯环化的氮丙啶酯的合成方法。提出了两种不对称方法：衍生自α-氧代酯的α-硒基β-亚氨基酯的非对映选择性还原，产生顺式手性氮丙啶酯6和6 '；并且将手性酰胺非对映选择性共轭加成到α，β-不饱和酯上，从而提供反式手性氮丙啶酯6和6 ''。
• Screening of electrophilic compounds yields an aziridinyl peptide as new active-site directed SARS-CoV main protease inhibitor
  作者：Erika Martina、Nikolaus Stiefl、Björn Degel、Franziska Schulz、Alexander Breuning、Markus Schiller、Radim Vicik、Knut Baumann、John Ziebuhr、Tanja Schirmeister

  DOI：10.1016/j.bmcl.2005.09.012

  日期：2005.12

  The coronavirus main protease, M-pro, is considered a major target for drugs suitable to combat coronavirus infections including the severe acute respiratory syndrome (SARS). In this study, comprehensive HPLC- and FRET-substrate-based screenings of various electrophilic compounds were performed to identify potential M-pro inhibitors. The data revealec that the coronaviral main protease is inhibited by aziridine- and oxirane-2-carboxylates. Among the trans-configured aziridine-2.3-dicarboxylates the Gly-Gly-containing peptide 2c was found to be the most potent inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.
• Aziridines as templates: A general strategy for the stereospecific synthesis of 2-azetidinones
  作者：S. D. Sharma、Seema Kanwar、Shivani Rajpoot

  DOI：10.1002/jhet.5570430103

  日期：2006.1

  stereochemistry of these compounds has been determined by spectroscopic methods. Further, greater diversity of β-lactams via ring expansion of these azridines-2-carboxylates were obtained by a general, efficient and direct stereospecific approach.

  已经描述了获得各种氮丙啶-2-羧酸盐的各种途径，并且已经通过光谱法确定了这些化合物的立体化学。此外，β内酰胺类的更大的多样性通过由一般的，有效和直接的立体有择方法获得的这些azridines -2-羧酸酯的扩环。
• Carbonylation of Silylated Hydroxymethyl Aziridines to β-Lactams
  作者：Paolo Davoli、Irene Moretti、Fabio Prati、Howard Alper

  DOI：10.1021/jo981568h

  日期：1999.1.1

  Functionalized beta-lactams are synthesized by carbonylative ring expansion of silylated hydroxymethyl aziridines catalyzed by dicobalt octacarbonyl, a process that proceeds with inversion of configuration. Ring opening and elimination occurs on attempted carbonylation of aziridine carboxylates.