(2S,3S)-1-tert-butyl 2-methyl 3-methylaziridine-1,2-dicarboxylate | 891202-55-4

• 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)-1-tert-butyl 2-methyl 3-methylaziridine-1,2-dicarboxylate
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S,3S)-3-methylaziridine-1,2-dicarboxylate
• CAS: 891202-55-4
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: PXBJPFOJMVJJQV-YKFGJVJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1-tert-butyl 2-methyl 3-methylaziridine-1,2-dicarboxylate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 methyl (4S,5S)-5-methyl-2-oxooxazolidine-4-carboxylate
  参考文献：
  名称：

  Novel Synthesis of 4-Carboxymethyl 5-Alkyl/Aryl Oxazolidin-2-ones by Rearrangement of 2-Carboxymethyl 3-Alkyl/Aryl N-tert-Butoxycarbonyl Aziridines

  摘要：

  A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of a carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc p-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio and stereoselectivity.

  DOI：

  10.1021/ol991225l
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (2S,3S)-1-tert-butyl 2-methyl 3-methylaziridine-1,2-dicarboxylate
  参考文献：
  名称：

  Novel Synthesis of 4-Carboxymethyl 5-Alkyl/Aryl Oxazolidin-2-ones by Rearrangement of 2-Carboxymethyl 3-Alkyl/Aryl N-tert-Butoxycarbonyl Aziridines

  摘要：

  A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of a carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc p-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio and stereoselectivity.

  DOI：

  10.1021/ol991225l

文献信息

• Regiospecific reductive ring cleavage of N-substituted aziridine-2-carboxylates and an aziridine-2-methanol via catalytic hydrogenation using Pd as a catalyst
  作者：Yeonhwa Lim、Won Koo Lee

  DOI：10.1016/0040-4039(95)01814-x

  日期：1995.11

  Regiospecific reductive ring cleavage was accomplished in the reaction of N-α-methylbenzyl substituted aziridine-2-carboxylate and aziridine-2-methanol under a catalytic hydrogenation condition. The regiospecificity was determined by the substituent at C-2.

  N -α-甲基苄基取代的氮丙啶-2-羧酸酯和氮丙啶-2-甲醇在催化氢化条件下的反应完成了区域特异性还原环的裂解。区域特异性由C-2上的取代基确定。
• Chiral Seleno-Amines from Indium Selenolates. A Straightforward Synthesis of Selenocysteine Derivatives
  作者：Antonio L. Braga、Paulo H. Schneider、Marcio W. Paixão、Anna M. Deobald、Clovis Peppe、Diana P. Bottega

  DOI：10.1021/jo060286b

  日期：2006.5.1

  A simple and efficient procedure for the synthesis of chiral beta-seleno-amines derivatives from a one-pot indium(I) iodide-mediated aziridine ring opening with diorganoyl diselenides has been developed. As an application, the synthesis of selenocysteine and selenotreonine derivatives has been accomplished.
• Novel Synthesis of 4-Carboxymethyl 5-Alkyl/Aryl Oxazolidin-2-ones by Rearrangement of 2-Carboxymethyl 3-Alkyl/Aryl <i>N</i>-<i>tert</i>-Butoxycarbonyl Aziridines
  作者：Claudia Tomasini、Andrea Vecchione

  DOI：10.1021/ol991225l

  日期：1999.12.1

  A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of a carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc p-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio and stereoselectivity.