6-Amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-D-allonolactam | 145372-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 6-Amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-D-allonolactam
• 英文别名: (1R,2R,6R,7R)-4,4-dimethyl-3,5,11-trioxa-9-azatricyclo[5.3.1.02,6]undecan-8-one
• CAS: 145372-89-0
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: HRASSOIKVFMWKW-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Methyl 2,5-anhydro-6-azido-6-deoxy-3,4-O-isopropylidene-D-allonate 在 钯 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到6-Amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-D-allonolactam
  参考文献：
  名称：

  Tetrahydrofuran amino acids: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid

  摘要：

  报道了一种D-allo-5-(叠氮甲基)四氢呋喃-2-羧酸酯的合成，该化合物作为氨基酸前驱体（其羧酸与叠氮甲基取代基为顺式，与二醇部分为反式）。文中描述了该单体的寡聚化，生成二聚体、四聚体和八聚体的碳肽类化合物。同时，对环己烯基保护的寡聚体和一个解保护的四聚体（具有八个自由羟基）在溶液中的结构进行了NMR研究。

  DOI：

  10.1039/b002996n

文献信息

• The ring contraction of δ-lactones with leaving group α-substituents: a strategy for the synthesis of 2,5-disubstituted highly functionalised homochiral tetrahydrofurans
  作者：Sik-Man S. Choi、Paul M. Myerscough、Antony J. Fairbanks、Ben M. Skead、Claire J. F. Bichard、Simon J. Mantell、Jong Chan Son、George W. J. Fleet、John Saunders、David Brown

  DOI：10.1039/c39920001605

  日期：——

  Treatment of derivatives of δ-lactones having a leaving group at C-2 with methanol in the presence of base gives methyl tetrahydrofuran-α-carboxylates in good to excellent yield with a high degree of stereocontrol of the carbon substituents at C-2 and C-5.

  在碱存在下，用甲醇处理C-2位带有保护基的γ-内酯衍生物，可以得到甲基四氢呋喃-γ-羧酸酯，收率良好到极佳，且C-2和C-5位碳取代基具有高度的立体选择性。
• From sequencamers to foldamers? Tetrameric furanose carbopeptoids from cis- and trans-5-aminomethyl-tetrahydrofuran-2-carboxylates
  作者：Daniel D. Long、Natasha L. Hungerford、Martin D. Smith、Dominic E.A. Brittain、Daniel G. Marquess、Timothy D.W. Claridge、George W.J. Fleet

  DOI：10.1016/s0040-4039(99)00110-0

  日期：1999.3

  The synthesis of three stereoisomeric cis- and trans-5-azidomelhyl-tetrahydrofuran-2-carboxylates in which a ketal-protected cis-diol unit is present is described. The monomers undergo efficient oligomerisation to tetrameric carbopeptoids in which the diol protection facilitates ready purification by chromatography which augurs well for the formation of homogeneous higher polymers. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Tetrahydrofuran amino acids: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid
  作者：Natasha L. Hungerford、Timothy D. W. Claridge、Mark P. Watterson、Robin T. Aplin、Andres Moreno、George W. J. Fleet

  DOI：10.1039/b002996n

  日期：——

  The synthesis of a D-allo-5-(azidomethyl)tetrahydrofuran-2-carboxylate as an amino acid precursor (in which the carboxylic acid is cis to the azidomethyl substituent and trans to the diol moiety) is reported from D-ribose. The oligomerisation of this monomer to dimeric, tetrameric and octameric carbopeptoids is described. NMR studies into the solution structures of cyclohexylidene-protected oligomers and of a deprotected tetramer with eight free hydroxy groups are described.

  报道了一种D-allo-5-(叠氮甲基)四氢呋喃-2-羧酸酯的合成，该化合物作为氨基酸前驱体（其羧酸与叠氮甲基取代基为顺式，与二醇部分为反式）。文中描述了该单体的寡聚化，生成二聚体、四聚体和八聚体的碳肽类化合物。同时，对环己烯基保护的寡聚体和一个解保护的四聚体（具有八个自由羟基）在溶液中的结构进行了NMR研究。