(8S)-isocaryolan-9-one | 203437-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8S)-isocaryolan-9-one
• 英文别名: (1S,2S,5R,8S)-1,4,4-trimethyltricyclo[6.3.1.02,5]dodecan-9-one
• CAS: 203437-38-1
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: YMEIZAGUTPNLQD-OXIQGZBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (8S)-isocaryolan-9-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (8S,9R)-isocaryolan-9-ol
  参考文献：
  名称：

  Phytotoxic Activity and Metabolism of Botrytis cinerea and Structure–Activity Relationships of Isocaryolane Derivatives

  摘要：

  Research has been conducted on the biotransformation Of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo [6.2.1.0(2'5)] uridecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)- Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3,4a, and 5a, together with. their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 are, described for the first time.

  DOI：

  10.1021/np3009013
• 作为产物：
  描述：

  caryophylla-4(12),8(13)-dien-5α-ol 在 氢溴酸 、 四氰基乙烯 作用下， 以 丙酮 为溶剂， 生成 (8S)-isocaryolan-9-one
  参考文献：
  名称：

  Phytotoxic Activity and Metabolism of Botrytis cinerea and Structure–Activity Relationships of Isocaryolane Derivatives

  摘要：

  Research has been conducted on the biotransformation Of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo [6.2.1.0(2'5)] uridecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)- Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3,4a, and 5a, together with. their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 are, described for the first time.

  DOI：

  10.1021/np3009013

文献信息

• Exploring the Chemical Space Accessed by Chiral Pool Terpenes. The (−)-Caryophyllene Oxide Paradigm
  作者：Theodora Athanasiadou、Georgia G. Bagkavou、Polymnia Karagianni、Christos I. Stathakis

  DOI：10.1021/acs.orglett.4c00132

  日期：2024.4.19

  Terpenes represent a flourishing source of structural motifs that can be converted into several more complex architectures. Realization of such transformations in a concise and efficient manner adds great value to the starting material. Herein, we study the case of (−)-caryophyllene oxide and convert it into natural sesquiterpenoids (rumphellolide K, rumphellaone A, and antipacid A), thus expanding

  萜烯代表了结构图案的丰富来源，可以转化为几种更复杂的结构。以简洁有效的方式实现这种转变为起始材料增加了巨大的价值。在此，我们研究了(−)-石竹烯氧化物的情况，并将其转化为天然倍半萜类化合物（rumphellolide K、rumphellaone A 和 antipacid A），从而扩大了其特权结构所访问的化学空间。我们的半合成很短，并且依赖于试剂决定的立体选择性和化学选择性。