6-Amino-6-deoxy-D-gluconolactam | 14199-62-3

• 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-6-deoxy-D-gluconolactam
• 英文别名: 6-amino-6-deoxy-gluconolactam；6-amino-6-deoxy-D-glucono-1,6-lactam；3R,4S,5R,6R-tetrahydroxyazepan-2-one；6-Amino-6-desoxy-D-glucono-ε-lactam；(3R,4S,5R,6R)-3,4,5,6-tetrahydroxyazepan-2-one
• CAS: 14199-62-3
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: REUKDNVLJSOKNV-SQOUGZDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  12
• 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：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Amino-6-deoxy-D-gluconolactam 在 dimethyl sulfide borane 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.17h， 生成 1,6-dideoxy-1,6-imino-(2S,3R,4R,5R)-D-glucitol hydrochloride
  参考文献：
  名称：

  Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-glucitol)

  摘要：

  Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00757-3
• 作为产物：
  描述：

  methyl 6-deoxy-6-iodo-2,3,4,5-tetra-O-acetyl-D-gluconate 在 potassium cyanide 、 叠氮化锂 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、303.98 kPa 条件下， 反应 86.0h， 生成 6-Amino-6-deoxy-D-gluconolactam
  参考文献：
  名称：

  Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-glucitol)

  摘要：

  Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00757-3

文献信息

• Kefurt, Karel; Kefurtova, Zdenka; Jary, Jiri, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 11, p. 2665 - 2673
  作者：Kefurt, Karel、Kefurtova, Zdenka、Jary, Jiri

  DOI：——

  日期：——
• Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-glucitol)
  作者：Cosam C Joseph、Henk Regeling、Binne Zwanenburg、Gordon J.F Chittenden

  DOI：10.1016/s0040-4020(02)00757-3

  日期：2002.8

  Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.