methyl (2S,1'R)-1-(1'-phenylethyl)-aziridine-2-carboxylate | 68820-70-2

• 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: methyl (2S,1'R)-1-(1'-phenylethyl)-aziridine-2-carboxylate
• 英文别名: methyl 1-(1R-phenylethyl)-aziridine-2S-carboxylate；Srmsdiadujogry-pphwzaggsa-；methyl (2S)-1-[(1R)-1-phenylethyl]aziridine-2-carboxylate
• CAS: 68820-70-2
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: SRMSDIADUJOGRY-PPHWZAGGSA-N

物化性质

• 沸点：
  259.4±33.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  methyl (2S,1'R)-1-(1'-phenylethyl)-aziridine-2-carboxylate 在 sodium tetrahydroborate 、 lithium chloride 作用下， 反应 16.0h， 以79%的产率得到(S)-1-[(R)-α-甲基苄基]氮杂环丙烷-2-甲醇
  参考文献：
  名称：

  Synthesis of the four enantiomers of diethyl 1,2-di(N-Boc-amino)propylphosphonates

  摘要：

  A simple and efficient synthetic strategy to all four enantiomerically pure diethyl 1,2-di(N-Boc-amino) propylphosphonates has been elaborated starting from the corresponding N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes, employing a one-pot three-components Kabachnik-Fields reaction followed by the hydrogenolytic removal of the chiral auxiliary and aziridine ring opening with simultaneous protection of the amino groups as the N-Boc derivatives. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.09.003
• 作为产物：
  描述：

  重氮乙酸甲酯 、 1,3,5-tri([R]-α-methylbenzyl)-1,3,5-triazine 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl (2S,1'R)-1-(1'-phenylethyl)-aziridine-2-carboxylate 、 methyl (2R,1'R)-1-(1'-phenylethyl)-aziridine-2-carboxylate
  参考文献：
  名称：

  在氯化锡（IV）存在下六氢-1,3,5-三嗪与烷基重氮乙酸酯的反应合成氮丙啶-2-羧酸酯的新方法

  摘要：

  在路易斯酸催化剂存在下，由六氢-1,3,5-三嗪与烷基重氮乙酸酯反应制备氮丙啶-2-羧酸酯。

  DOI：

  10.1016/0040-4039(96)01554-7

文献信息

• A new synthesis of aziridine-2-carboxylates by reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of tin(IV) chloride
  作者：Hyun-Joon Ha、Kyung-Ho Kang、Jang-Min Suh、Young-Gil Ahn

  DOI：10.1016/0040-4039(96)01554-7

  日期：1996.9

  Aziridine-2-carboxylates were prepared from the reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of Lewis acid catalyst in high yield.

  在路易斯酸催化剂存在下，由六氢-1,3,5-三嗪与烷基重氮乙酸酯反应制备氮丙啶-2-羧酸酯。
• Synthesis and configurational assignment of an unusual bicylic amino acid
  作者：Saleem Farooa、William E. Swain、Richard Daeppen、Grety Rihs

  DOI：10.1016/s0957-4166(00)82312-5

  日期：1992.1

  A synthesis leading to the racemic bicyclic amino acid 1 is described. Similarly, the two enantiomers of 1 have been synthesised and their configuration determined.
• Synthesis of four enantiomers of 2-acetamido-1-hydroxypropylphosphonates
  作者：Andrzej E. Wróblewski、Joanna Drozd

  DOI：10.1016/j.tetasy.2007.04.021

  日期：2007.5

  Enantiomerically pure diethyl 2-acetamido-1-hydroxypropylphosphonates were synthesised from N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes via phosphonylation followed by acetylation of the hydroxy groups and the simultaneous hydrogenolytic cleavage of the aziridine rings and the removal of the chiral auxiliaries. In addition, enantiomerically pure diethyl (1S,2R)- and (1R,2S)-2-amino-1-hydroxypropylphosphonates (the phosphonate analogues of isothreonine) were separated. (C) 2007 Elsevier Ltd. All rights reserved.
• A new synthesis of aziridine-2-carboxylates: Reaction of hexahydro-1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of lewis acid
  作者：Hyun-Joon Ha、Jang-Min Suh、Kyung-Ho Kang、Young-Gil Ahn、Oksoo Han

  DOI：10.1016/s0040-4020(97)10358-1

  日期：1998.1

  Aziridine-2-carboxylates were prepared from the reaction of hexahydro-1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid catalyst in high yield. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Synthesis of the four enantiomers of diethyl 1,2-di(N-Boc-amino)propylphosphonates
  作者：Iwona E. Głowacka、Dorota G. Piotrowska、Andrzej E. Wróblewski、Aleksandra Trocha

  DOI：10.1016/j.tetasy.2017.09.003

  日期：2017.11

  A simple and efficient synthetic strategy to all four enantiomerically pure diethyl 1,2-di(N-Boc-amino) propylphosphonates has been elaborated starting from the corresponding N-[(R)-(1-phenylethyl)]aziridine-(2S)- and N-[(S)-(1-phenylethyl)]aziridine-(2R)-carboxaldehydes, employing a one-pot three-components Kabachnik-Fields reaction followed by the hydrogenolytic removal of the chiral auxiliary and aziridine ring opening with simultaneous protection of the amino groups as the N-Boc derivatives. (C) 2017 Elsevier Ltd. All rights reserved.