N-benzyl-cis-3,4-dihydroxy-2-oxoazepane

• 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: N-benzyl-cis-3,4-dihydroxy-2-oxoazepane
• 英文别名: (3R,4R)-1-benzyl-3,4-dihydroxyazepan-2-one
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: RHQNGZIOEQLEGR-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-cis-3,4-dihydroxy-2-oxoazepane 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 sodium azide 、 三氟甲磺酸酐 、 三氟化硼乙醚 、 水 、 苄基三甲基溴化铵 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 [(3R,4R)-1-benzyl-3-[(4-phenylmethoxybenzoyl)amino]azepan-4-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Balanol¹

  摘要：

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.

  DOI：

  10.1021/jo952280k
• 作为产物：
  描述：

  己内酰胺 在 四氧化锇 、 双氧水 、 sodium hydride 、 N-甲基吗啉氧化物 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 丙酮 、 paraffin 、 叔丁醇 为溶剂， 反应 45.5h， 生成 N-benzyl-cis-3,4-dihydroxy-2-oxoazepane
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Balanol¹

  摘要：

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.

  DOI：

  10.1021/jo952280k

文献信息

• Two efficient syntheses of (±)-anti-N-benzyl-3-amino-4-hydroxyhexahydroazepine
  作者：Hong Hu、G. Erik Jagdmann、Philip F. Hughes、Jeffrey B. Nichols

  DOI：10.1016/0040-4039(95)00623-k

  日期：1995.5

  Functionalization of ε-caprolactam (3) or Beckmann rearrangement of the syn-oxime derivative of 3-ethoxy-2-cyclohexen-1-one (12) provided efficient and high-yielding syntheses of (±)-anti-N-benzyl-3-amino-4-hydroxyhexahydroazepine (2), a key intermediate for the syntheses of racemic balanol and its analogs.

  ε-己内酰胺（3）的功能化或3-乙氧基-2-环己烯-1-酮（12）的肟肟衍生物的贝克曼重排提供了（±）-抗-N-苄基-的高效高产合成3-氨基-4-羟基六氢a庚因（2），是外消旋巴拉诺醇及其类似物合成的关键中间体。
• Total Synthesis of (−)- and (+)-Balanol¹
  作者：John W. Lampe、Philip F. Hughes、Christopher K. Biggers、Shelley H. Smith、Hong Hu

  DOI：10.1021/jo952280k

  日期：1996.1.1

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.