(2R,5S)-2-Isopropenyl-6-methyl-spiro[4.5]dec-7-en-6-ol | 186357-54-0

• 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: (2R,5S)-2-Isopropenyl-6-methyl-spiro[4.5]dec-7-en-6-ol
• CAS: 186357-54-0
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: KDXZDZOSZNPKSK-YIOYIWSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2-Isopropenyl-6-methyl-spiro[4.5]dec-7-en-6-ol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(-)-(2R,5R)-2-isopropenyl-6-methylspiro[4.5]dec-6-en-8-one
  参考文献：
  名称：

  Total synthesis of (–)-solavetivone using enantioselective copper-catalysed conjugate addition of Me₃Al to a cyclohexa-2,5-dienone intermediate

  摘要：

  By applying a new enantioselective Cu-catalysed conjugate addition of Me(3)Al, (-)-solavetivone 1 is synthesized stereoselectively from cyclohexa-2,5-dienone 4, prepared from a chiral compound 6 using a regioselective Hg-II-mediated cyclopropyl ring-opening, subsequent Pd-II-mediated spiroannulation of 7, and a stereoselective Pd-0-catalysed hydrogenation of an allylic formate 5 as key reactions.

  DOI：

  10.1039/cc9960001655
• 作为产物：
  描述：

  [(2E)-2-[(5S)-10-(4-methylphenyl)sulfonylspiro[4.5]dec-9-en-3-ylidene]propyl] formate 在 叔丁基过氧化氢 、 bis(acetylacetonato)palladium(II) 、 三丁基膦 、 potassium hydride 、 甲酸:三乙胺 1:1 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 苯 为溶剂， 反应 76.0h， 生成 (2R,5S)-2-Isopropenyl-6-methyl-spiro[4.5]dec-7-en-6-ol
  参考文献：
  名称：

  Total synthesis of (–)-solavetivone using enantioselective copper-catalysed conjugate addition of Me₃Al to a cyclohexa-2,5-dienone intermediate

  摘要：

  By applying a new enantioselective Cu-catalysed conjugate addition of Me(3)Al, (-)-solavetivone 1 is synthesized stereoselectively from cyclohexa-2,5-dienone 4, prepared from a chiral compound 6 using a regioselective Hg-II-mediated cyclopropyl ring-opening, subsequent Pd-II-mediated spiroannulation of 7, and a stereoselective Pd-0-catalysed hydrogenation of an allylic formate 5 as key reactions.

  DOI：

  10.1039/cc9960001655

文献信息

• Total synthesis of (–)-solavetivone using enantioselective copper-catalysed conjugate addition of Me₃Al to a cyclohexa-2,5-dienone intermediate
  作者：Yoshiji Takemoto、Satoru Kuraoka、Taiichi Ohra、Yasuhiro Yonetoku、Chuzo Iwata

  DOI：10.1039/cc9960001655

  日期：——

  By applying a new enantioselective Cu-catalysed conjugate addition of Me(3)Al, (-)-solavetivone 1 is synthesized stereoselectively from cyclohexa-2,5-dienone 4, prepared from a chiral compound 6 using a regioselective Hg-II-mediated cyclopropyl ring-opening, subsequent Pd-II-mediated spiroannulation of 7, and a stereoselective Pd-0-catalysed hydrogenation of an allylic formate 5 as key reactions.