2-[(1aR,2aS,5S,5aR,7aS)-2a,7a-dimethyl-1a,2,3,4,5,5a,6,7-octahydroazuleno[5,6-b]oxiren-5-yl]but-3-en-2-ol | 461663-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(1aR,2aS,5S,5aR,7aS)-2a,7a-dimethyl-1a,2,3,4,5,5a,6,7-octahydroazuleno[5,6-b]oxiren-5-yl]but-3-en-2-ol
• CAS: 461663-47-8
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: XQPIFPJSWZIHMM-DHNXDVFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1aR,2aS,5S,5aR,7aS)-2a,7a-dimethyl-1a,2,3,4,5,5a,6,7-octahydroazuleno[5,6-b]oxiren-5-yl]but-3-en-2-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以14.4 mg的产率得到13(15)-3β,4β-epoxy-17,18,19,20-tetranorsphenolob-13(15)-en-16-al
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)E,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)Z,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond

  摘要：

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.

  DOI：

  10.1021/jo020287d
• 作为产物：
  描述：

  3-[(1S)-1,4-dimethyl-7-triethylsilyloxycyclohept-3-en-1-yl]propyl 4-methylbenzenesulfonate 在 吡啶 、 氯化亚砜 、 jones reagent 、 18-冠醚-6 、 potassium tert-butylate 、 potassium carbonate 、 magnesium 、 N,N-二甲基甲酰胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 30.5h， 生成 2-[(1aR,2aS,5S,5aR,7aS)-2a,7a-dimethyl-1a,2,3,4,5,5a,6,7-octahydroazuleno[5,6-b]oxiren-5-yl]but-3-en-2-ol
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)E,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)Z,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond

  摘要：

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.

  DOI：

  10.1021/jo020287d

文献信息

• Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)<i>E</i>,16<i>E</i>-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)<i>Z</i>,16<i>E</i>-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond
  作者：Katsuyuki Nakashima、Kosuke Inoue、Masakazu Sono、Motoo Tori

  DOI：10.1021/jo020287d

  日期：2002.8.1

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.