1-benzyloxy-3-(S)-hydroxymethylaziridine-2-(R)-carboxylic acid tert-butyl ester | 264147-90-2

• 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: 1-benzyloxy-3-(S)-hydroxymethylaziridine-2-(R)-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S)-3-(hydroxymethyl)-1-phenylmethoxyaziridine-2-carboxylate
• CAS: 264147-90-2
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: FPHKMHHHKMJREA-SXMVJOELSA-N

物化性质

• 沸点：
  384.9±52.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-3-(S)-hydroxymethylaziridine-2-(R)-carboxylic acid tert-butyl ester 在 2,6-二甲基吡啶 、 二异丁基氢化铝 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 121.5h， 生成 3-[1-benzyloxy-3-(R)-(tert-butyldimethylsilanyloxymethyl)aziridin-2-(S)-ylmethoxy]pyridine
  参考文献：
  名称：

  Design and synthesis of MMP inhibitors using N -arylsulfonylaziridine hydroxamic acids as constrained scaffolds

  摘要：

  The synthesis of cis- and trans-aziridine hydroxamic acid derivatives as MMP inhibitors is described using enantio- and diastereoselective methods for the formation of trisubstituted aziridines. Their preliminary inhibitory activity is reported and discussed in the context of modeling studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00641-x
• 作为产物：
  描述：

  (E)-1-benzyloxy-3-(R)-[2-(1,3-dimethyl-2-oxo-4-(R)-5-(R)-[octahydro-2λ⁵-benzo[1.3.2]diazaphosphol-2-yl)vinyl]aziridine]-2-(R)-carboxylic acid tert-butyl ester 在 臭氧 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以94%的产率得到1-benzyloxy-3-(S)-hydroxymethylaziridine-2-(R)-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  The synthesis of enantiomerically pure disubstituted aziridines and N-alkoxy aziridines

  摘要：

  The addition of a chloroallyl phosphonamide anion to oximes has allowed the preparation of a variety of cis-disubstituted N-alkoxy aziridines in enantiomerically pure form. Oxidative cleavage of the chiral auxiliary followed by derivatization of the products has allowed the preparation of enantiopure N-alkoxy aziridines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02211-x

文献信息

• The synthesis of enantiomerically pure disubstituted aziridines and N-alkoxy aziridines
  作者：Stephen Hanessian、Louis-David Cantin

  DOI：10.1016/s0040-4039(99)02211-x

  日期：2000.2

  The addition of a chloroallyl phosphonamide anion to oximes has allowed the preparation of a variety of cis-disubstituted N-alkoxy aziridines in enantiomerically pure form. Oxidative cleavage of the chiral auxiliary followed by derivatization of the products has allowed the preparation of enantiopure N-alkoxy aziridines. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Design and synthesis of MMP inhibitors using N -arylsulfonylaziridine hydroxamic acids as constrained scaffolds
  作者：Stephen Hanessian、Nicolas Moitessier、Louis-David Cantin

  DOI：10.1016/s0040-4020(01)00641-x

  日期：2001.8

  The synthesis of cis- and trans-aziridine hydroxamic acid derivatives as MMP inhibitors is described using enantio- and diastereoselective methods for the formation of trisubstituted aziridines. Their preliminary inhibitory activity is reported and discussed in the context of modeling studies. (C) 2001 Elsevier Science Ltd. All rights reserved.