solavetivone | 54878-25-0

• 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: solavetivone
• CAS: 54878-25-0
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: FGCUSSRGQNHZRW-ILWWEHDPSA-N

物化性质

• 沸点：
  321.4±42.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  solavetivone 在 Amberlyst IR-15 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以42.2%的产率得到(+/-)-10-epi-β-vetivone
  参考文献：
  名称：

  WO2008/116056

  摘要：

  公开号：
• 作为产物：
  描述：

  premnaspirodiene 在 3,5-二甲基吡唑 、 二氯氧化铬 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 以71%的产率得到solavetivone
  参考文献：
  名称：

  Silicon-promoted ring contractions in the formation of carbocyclic spiro compounds. Total synthesis of (-)-solavetivone

  摘要：

  A new method involving silicon-promoted ring contraction was developed for the synthesis of carbocyclic spiro compounds. In the presence of a Lewis acid, (trimethylsilyl)decalinol 12 and (trimethylsilyl)declain expoide 11 underwent ring contraction in a highly stereoselective manner to afford spiro[4.5]dec-6-enes 14 and 19, respectively. The first total synthesis of optically active solavetivone ((-)-1) was accomplished in 13 steps by use of this new type of reaction as the key step. Utilization of the silicon-promoted ring contraction solves three problems associated with spiro compound synthesis: (1) efficient generation of the quaternary carbon spiro center, (2) full control of the stereoconfiguration of the spiro center during its formation, and (3) stereospecific establishment of chiral centers on both rings of the spiro unit.

  DOI：

  10.1021/jo00029a025

文献信息

• OXYSOLAVETIVONE. A NEW BIOSYNTHETIC PRECURSOR OF LUBIMIN IN POTATO
  作者：Akio Murai、Yuko Yoshizawa、Nobukatsu Katsui、Shingo Sato、Tadashi Masamune

  DOI：10.1246/cl.1986.771

  日期：1986.5.5

  The title compound, isolated newly as a metabolite from solavetivone, was converted into lubimin in potato.

  该复合物是新近从索拉维酮中分离出的代谢产物，在马铃薯中转化为鲁米诺。
• 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.
• WO2008/116056
  申请人：——

  公开号：——

  公开（公告）日：——
• Silicon-promoted ring contractions in the formation of carbocyclic spiro compounds. Total synthesis of (-)-solavetivone
  作者：Jih Ru Hwu、John M. Wetzel

  DOI：10.1021/jo00029a025

  日期：1992.1

  A new method involving silicon-promoted ring contraction was developed for the synthesis of carbocyclic spiro compounds. In the presence of a Lewis acid, (trimethylsilyl)decalinol 12 and (trimethylsilyl)declain expoide 11 underwent ring contraction in a highly stereoselective manner to afford spiro[4.5]dec-6-enes 14 and 19, respectively. The first total synthesis of optically active solavetivone ((-)-1) was accomplished in 13 steps by use of this new type of reaction as the key step. Utilization of the silicon-promoted ring contraction solves three problems associated with spiro compound synthesis: (1) efficient generation of the quaternary carbon spiro center, (2) full control of the stereoconfiguration of the spiro center during its formation, and (3) stereospecific establishment of chiral centers on both rings of the spiro unit.