(5S,6R)-5,6-二羟基-2-氮杂环庚酮 | 230307-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: (5S,6R)-5,6-二羟基-2-氮杂环庚酮
• 英文名称: 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam
• 英文别名: (5S,6R)-5,6-dihydroxyazepan-2-one
• CAS: 230307-31-0
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: ZQBBYLAQPWMOAV-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙酮 、 (5S,6R)-5,6-二羟基-2-氮杂环庚酮 在 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 (5S,6R)-5,6-O-isopropylidene-azepane-2-one
  参考文献：
  名称：

  Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (−)-balanol

  摘要：

  Sugar lactones were converted to 3,4-disubstituted azepanes and caprolactam derivatives by selective deoxygenation, functionalization and reductive cyclization. The cyclization proved troublesome with 6-azidolactols but led to good results with the corresponding lactones. A formal synthesis of (+)- and (-)-balanol is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00466-8
• 作为产物：
  描述：

  6-azido-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到(5S,6R)-5,6-二羟基-2-氮杂环庚酮
  参考文献：
  名称：

  Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam

  摘要：

  Solid-state conformations of 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation C-4(1,N) was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the similar to 1:1 equilibrium of the conformers C-4(1,N) and C-1,N(4). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00319-5

文献信息

• Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (−)-balanol
  作者：Claus Herdeis、Rafat M Mohareb、Reinhard B Neder、Franz Schwabenländer、Joachim Telser

  DOI：10.1016/s0957-4166(99)00466-8

  日期：1999.12

  Sugar lactones were converted to 3,4-disubstituted azepanes and caprolactam derivatives by selective deoxygenation, functionalization and reductive cyclization. The cyclization proved troublesome with 6-azidolactols but led to good results with the corresponding lactones. A formal synthesis of (+)- and (-)-balanol is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam
  作者：Michaela Hamernı́ková、Svetlana Pakhomova、Jaroslav Havlı́ček、Hana Votavová、Karel Kefurt

  DOI：10.1016/s0008-6215(99)00319-5

  日期：2000.3

  Solid-state conformations of 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation C-4(1,N) was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the similar to 1:1 equilibrium of the conformers C-4(1,N) and C-1,N(4). (C) 2000 Elsevier Science Ltd. All rights reserved.