(2S,3R)-2,3-dimethyl-2-[(Z)-3-methylpent-2-en-4-ynyl]cyclohexan-1-one | 1191092-50-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3R)-2,3-dimethyl-2-[(Z)-3-methylpent-2-en-4-ynyl]cyclohexan-1-one
• CAS: 1191092-50-8
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: PZJKHDOKRHPSRJ-KRFXKNSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,3-dimethyl-2-[(Z)-3-methylpent-2-en-4-ynyl]cyclohexan-1-one 在 二氯二茂锆 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 、 (1S,2S,3R)-2,3-dimethyl-2-[(2Z)-3-methylpenta-2,4-dienyl]cyclohexan-1-ol
  参考文献：
  名称：

  Synthesis of (+)-striatene: confirmation of its stereostructure

  摘要：

  The first enantioselective synthesis of natural striatene (+)-1, isolated from liverwort Ptychanthus striatus, starting from commercially available (R)-Pulegone is described. Its stereostructure was confirmed by X-ray analysis of a 3,5-dinitrobenzoate derivative obtained from a key intermediate and its high optical purity was verified by chiral HPLC. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.138
• 作为产物：
  描述：

  (Z)-1-bromo-3-methylpent-2-en-4-yne 、 (R)-(2,3-dimethylcyclohex-1-enyloxy)trimethylsilane 在 甲基锂 作用下， 以 乙醚 、 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 13.0h， 以73%的产率得到(2S,3R)-2,3-dimethyl-2-[(Z)-3-methylpent-2-en-4-ynyl]cyclohexan-1-one
  参考文献：
  名称：

  Synthesis of (+)-striatene: confirmation of its stereostructure

  摘要：

  The first enantioselective synthesis of natural striatene (+)-1, isolated from liverwort Ptychanthus striatus, starting from commercially available (R)-Pulegone is described. Its stereostructure was confirmed by X-ray analysis of a 3,5-dinitrobenzoate derivative obtained from a key intermediate and its high optical purity was verified by chiral HPLC. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.138