p-nitrophenyl (-)-(1'S,2'R,5'R)-(2',7'-epoxy-2'-isopropyl-5'-methylcyclohex-1'-yl)acetate | 862159-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: p-nitrophenyl (-)-(1'S,2'R,5'R)-(2',7'-epoxy-2'-isopropyl-5'-methylcyclohex-1'-yl)acetate
• 英文别名: (4-nitrophenyl) 2-[(3R,4S,6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-yl]acetate
• CAS: 862159-04-4
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: KPOCIRNYPFGQKC-FHSNZYRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl (-)-(1'S,2'R,5'R)-(2',7'-epoxy-2'-isopropyl-5'-methylcyclohex-1'-yl)acetate 在 高氯酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (1S,4R,6S)-1-(1'-hydroxy-1'-methylethyl)-4-methyl-9-oxabicyclo[4.3.0]nonan-8-one 、 (1R,6S,8R)-1-hydroxy-2,2,8-trimethyl-3-oxabicyclo[4.4.0]decan-4-one
  参考文献：
  名称：

  Lactones 23: Synthesis of cis-fused bicyclic hydroxy lactones with a p-menthane system

  摘要：

  Enantiomeric pairs of cis-fused bicyclic hydroxy lactones with a p-menthane system were obtained in a several step synthesis from enantiornerically pure isomers of (+)-(R)- and (-)-(S)-pulegone. One-pot allyl-Claisen rearrangement of cis-pulegols, epoxidation of gamma,delta-unsaturated p-nitrophenyl esters and acidic lactonization of epoxy esters are key synthetic steps. The structures of the compounds were confirmed by both spectroscopic and crystallographic methods. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.020
• 作为产物：
  描述：

  (5'R)-(2'-isopropylidene-5'-methylcyclohex-1'-yl)acetic acid 在 五氯化磷 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 p-nitrophenyl (-)-(1'S,2'R,5'R)-(2',7'-epoxy-2'-isopropyl-5'-methylcyclohex-1'-yl)acetate
  参考文献：
  名称：

  Lactones 23: Synthesis of cis-fused bicyclic hydroxy lactones with a p-menthane system

  摘要：

  Enantiomeric pairs of cis-fused bicyclic hydroxy lactones with a p-menthane system were obtained in a several step synthesis from enantiornerically pure isomers of (+)-(R)- and (-)-(S)-pulegone. One-pot allyl-Claisen rearrangement of cis-pulegols, epoxidation of gamma,delta-unsaturated p-nitrophenyl esters and acidic lactonization of epoxy esters are key synthetic steps. The structures of the compounds were confirmed by both spectroscopic and crystallographic methods. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.020