(3aS,7R,8R,8aS)-7,8-二羟基-2,2-二甲基六氢-4H-[1,3]二氧杂环戊并[4,5-c]氮杂卓-4-酮 | 479412-95-8

• 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: (3aS,7R,8R,8aS)-7,8-二羟基-2,2-二甲基六氢-4H-[1,3]二氧杂环戊并[4,5-c]氮杂卓-4-酮
• 英文名称: 1,6-dideoxy-2,3-O-isopropylidene-1,6-imino-D-mannonolactam
• 英文别名: (3aS,7R,8R,8aS)-7,8-dihydroxy-2,2-dimethyl-3a,5,6,7,8,8a-hexahydro-[1,3]dioxolo[4,5-c]azepin-4-one
• CAS: 479412-95-8
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: DPJLDHKWDXEKSQ-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,7R,8R,8aS)-7,8-二羟基-2,2-二甲基六氢-4H-[1,3]二氧杂环戊并[4,5-c]氮杂卓-4-酮 在 硼烷四氢呋喃络合物 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 44.0h， 以80%的产率得到(3R,4R,5R,6R)-氮杂环庚烷-3,4,5,6-四醇盐酸盐
  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：

  D-甘露糖-1,4-内酯 在 palladium on activated charcoal 叠氮化锂 、 四溴化碳 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 (3aS,7R,8R,8aS)-7,8-二羟基-2,2-二甲基六氢-4H-[1,3]二氧杂环戊并[4,5-c]氮杂卓-4-酮
  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

• 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.