clovan-2,9-dione | 215663-13-1

• 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: clovan-2,9-dione
• 英文别名: (1S,5S,8R)-4,4,8-trimethyltricyclo[6.3.1.01,5]dodecane-2,9-dione
• CAS: 215663-13-1
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: FGHWBFRAAVLHJZ-VQISRLSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  clovan-2,9-dione 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 ((3aR)-5c-carboxy-1,1,5t-trimethyl-3-oxo-(7ac)-octahydro-inden-3ar-yl)-acetic acid
  参考文献：
  名称：

  丁香和β-石竹烯醇

  摘要：

  DOI：

  10.1039/jr9540002265
• 作为产物：
  描述：

  丁香三环烷二醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以86%的产率得到clovan-2,9-dione
  参考文献：
  名称：

  The Biotransformation of Some Clovanes by Botrytis cinerea

  摘要：

  The metabolism of the fungistatic agent 2 beta-methoxyclovan-9 alpha-ol (2) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 2 yielded compounds 3-5, 7, and 9. The major metabolites of compound 2 each show much reduced biological activity when compared with the parent compound. Also studied were the effects of B. cinerea on the metabolism of the related compounds 2 beta-methoxyclovan-9-one (3), 2 beta-methoxyclovan-9 beta-ol (4), and clovan-2,9-dione (6). Compounds 3, 4, 8, and 9 are described for the first time.

  DOI：

  10.1021/np9801054

文献信息

• Asymmetric Total Synthesis of (−)-Clovan-2,9-dione Using Rh(I)-Catalyzed [3 + 2 + 1] Cycloaddition of 1-Yne-vinylcyclopropane and CO
  作者：Jun Yang、Wenbo Xu、Qi Cui、Xing Fan、Lu-Ning Wang、Zhi-Xiang Yu

  DOI：10.1021/acs.orglett.7b02656

  日期：2017.11.17

  The asymmetric total synthesis of clovan-2,9-dione with a [6.3.1.01,5]dodecane skeleton has been achieved. The synthesis features a Rh(I)-catalyzed [3 + 2 + 1] cycloaddition of 1-yne-vinylcyclopropane (1-yne-VCP) with CO and an intramolecular aldol reaction to obtain the skeleton of the target molecule.

  已经实现了具有[6.3.1.0 1,5 ]十二烷骨架的clovan-2,9-dione的不对称全合成。该合成的特征在于，Rh（I）催化1-炔-乙烯基环丙烷（1-炔-VCP）与CO的[3 + 2 +1]环加成反应以及分子内羟醛反应获得目标分子的骨架。
• Aebi et al., Journal of the Chemical Society, 1954, p. 4659,4663
  作者：Aebi et al.

  DOI：——

  日期：——
• Aebi et al., Journal of the Chemical Society, 1953, p. 3124,3127
  作者：Aebi et al.

  DOI：——

  日期：——
• Clovene and β-caryophyllene alcohol
  作者：Albert W. Lutz、Evans B. Reid

  DOI：10.1039/jr9540002265

  日期：——
• The Biotransformation of Some Clovanes by <i>Botrytis cinerea</i>
  作者：Isidro G. Collado、James R. Hanson、Antonio J. Macías-Sánchez、D. Mobbs

  DOI：10.1021/np9801054

  日期：1998.11.1

  The metabolism of the fungistatic agent 2 beta-methoxyclovan-9 alpha-ol (2) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 2 yielded compounds 3-5, 7, and 9. The major metabolites of compound 2 each show much reduced biological activity when compared with the parent compound. Also studied were the effects of B. cinerea on the metabolism of the related compounds 2 beta-methoxyclovan-9-one (3), 2 beta-methoxyclovan-9 beta-ol (4), and clovan-2,9-dione (6). Compounds 3, 4, 8, and 9 are described for the first time.