(2S)-2-(3-hydroxypropyl)-2,5-dimethylcyclohept-4-en-1-ol | 679804-46-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-2-(3-hydroxypropyl)-2,5-dimethylcyclohept-4-en-1-ol
• CAS: 679804-46-7
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: SIBTZSANRXQCAG-KIYNQFGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-(3-hydroxypropyl)-2,5-dimethylcyclohept-4-en-1-ol 在 吡啶 、 氯化亚砜 、 jones reagent 、 18-冠醚-6 、 potassium tert-butylate 、 magnesium 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 29.0h， 生成 (1S,7R)-8-acetyl-1,4-dimethylbicyclo[5.3.0]dec-3-ene
  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：

  1,4-dimethyl-7-triethylsilyloxy-3-cycloheptenecarboxylate 在 氢氧化钾 、 lithium aluminium tetrahydride 、 jones reagent 、 (S)-(-)- α-甲基苄胺 、 对甲苯磺酸 作用下， 以 乙醚 、 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 99.5h， 生成 (2S)-2-(3-hydroxypropyl)-2,5-dimethylcyclohept-4-en-1-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