N-[(1R,5S,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide | 1560849-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(1R,5S,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide
• 英文别名: 4-epi-MT 35214
• CAS: 1560849-00-4
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: ROYHAMHLVIVHPH-ARDNSNSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 在 4-二甲氨基吡啶 、 迭氮酸 、 1,10-菲罗啉 、 氢氟酸 、 双氧水 、 碘 、 苄基三甲基氢氧化铵 、 caesium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 19.33h， 生成 N-[(1R,5S,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide
  参考文献：
  名称：

  Use of Aziridines for the Stereocontrolled Synthesis of (−)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214

  摘要：

  Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.

  DOI：

  10.1021/jo402535j

文献信息

• Use of Aziridines for the Stereocontrolled Synthesis of (−)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214
  作者：Christopher D. Maycock、Paula Rodrigues、M. Rita Ventura

  DOI：10.1021/jo402535j

  日期：2014.3.7

  Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.