(1S,2R,3S,7R,10S,11R)-5,5-dimethyl-4,6-dioxatetracyclo-[9.2.1.0.^2,100^3,7]tetradec-12-en-9-one | 1560848-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3S,7R,10S,11R)-5,5-dimethyl-4,6-dioxatetracyclo-[9.2.1.0.^2,100^3,7]tetradec-12-en-9-one
• CAS: 1560848-75-0
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: UBDXOZGGROZHTE-XAPBCISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,7R,10S,11R)-5,5-dimethyl-4,6-dioxatetracyclo-[9.2.1.0.^2,100^3,7]tetradec-12-en-9-one 在 4-二甲氨基吡啶 、 迭氮酸 、 1,10-菲罗啉 、 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 、 sodium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 四氯化碳 、 二苯醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 28.5h， 生成 N-[(1R,5R,6S)-5-[(tert-butyldimethylsilyl)oxy]-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
• 作为产物：
  描述：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 、 环戊二烯 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 0.42h， 以88%的产率得到(1S,2R,3S,7R,10S,11R)-5,5-dimethyl-4,6-dioxatetracyclo-[9.2.1.0.^2,100^3,7]tetradec-12-en-9-one
  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