(+)-(2R,5S)-2-isopropenyl-6-methylspiro-[4.5]dec-6,9-dien-8-one | 61167-63-3

• 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-methylspiro-[4.5]dec-6,9-dien-8-one
• 英文别名: (3R,5S)-10-methyl-3-prop-1-en-2-ylspiro[4.5]deca-6,9-dien-8-one
• CAS: 61167-63-3
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: WARYNZAAYWNCLP-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (+)-(2R,5S)-2-isopropenyl-6-methylspiro-[4.5]dec-6,9-dien-8-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 三甲基氯硅烷 、 三乙胺 、 palladium diacetate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 5.0h， 以90%的产率得到(+)-anhydro-β-rotunol
  参考文献：
  名称：

  Enantiospecific total synthesis of phytoalexins, (+)-solanascone, (+)-dehydrosolanascone, and (+)-anhydro-β-rotunol

  摘要：

  Enantiospecific total synthesis of the phytoalexins, solavetivone, anhydro-beta-rotunol, solailascone, and dehydrosolanascone, starting from the readily available monoterpene, (R)-carvone has been accomplished. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.124
• 作为产物：
  描述：

  (-)-(2R,5R)-2-isopropenyl-6-methylspiro[4.5]dec-6-en-8-one 生成 (+)-(2R,5S)-2-isopropenyl-6-methylspiro-[4.5]dec-6,9-dien-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

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.
• Enantiospecific total synthesis of phytoalexins, (+)-solanascone, (+)-dehydrosolanascone, and (+)-anhydro-β-rotunol
  作者：A. Srikrishna、S.S.V. Ramasastry

  DOI：10.1016/j.tetlet.2005.08.124

  日期：2005.10

  Enantiospecific total synthesis of the phytoalexins, solavetivone, anhydro-beta-rotunol, solailascone, and dehydrosolanascone, starting from the readily available monoterpene, (R)-carvone has been accomplished. (c) 2005 Elsevier Ltd. All rights reserved.