(1R,4aS,6S,8R,8aS)-8-Hydroxy-6,8a-dimethyl-5-methylene-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde | 875572-94-4

• 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: (1R,4aS,6S,8R,8aS)-8-Hydroxy-6,8a-dimethyl-5-methylene-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde
• 英文别名: (1R,4aS,6S,8R,8aS)-8-hydroxy-6,8a-dimethyl-5-methylidene-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
• CAS: 875572-94-4
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: AKSBEXNBIJAHCH-MKJLKUPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4aS,6S,8R,8aS)-8-Hydroxy-6,8a-dimethyl-5-methylene-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde 、 碘甲烷 在 silver(l) oxide 作用下， 反应 2.0h， 以14%的产率得到(1R,4aS,6S,8R,8aS)-8-Methoxy-6,8a-dimethyl-5-methylene-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde
  参考文献：
  名称：

  Fungicidal Sesquiterpene Dialdehyde Cinnamates from Pseudowintera axillaris

  摘要：

  Bioactivity-directed separation of a foliage extract from the New Zealand shrub Pseudowintera axillaris led to a compound with fungicidal activity against the plant pathogen Phytophthora infestans. This was identified as a new sesquiterpene dialdehyde cinnamate named paxidal. Two 6-hydroxy derivatives were present at lower levels in the extract. A further nine derivatives were synthesized from these natural products for a structure-activity study against a range of important food crop pathogens. The cinnamate group was important for fungicidal effects, and protection of the dialdehyde as a dimethyl acetal gave more potent, broader spectrum activity.

  DOI：

  10.1021/jf052585s
• 作为产物：
  描述：

  (E)-3-Phenyl-acrylic acid (1R,3S,5aS,7S,9R,9aS,9bR)-1,3-dimethoxy-7,9a-dimethyl-6-methylene-1,3,5,5a,6,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-9-yl ester 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 20.33h， 生成 (1R,4aS,6S,8R,8aS)-8-Hydroxy-6,8a-dimethyl-5-methylene-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde
  参考文献：
  名称：

  Fungicidal Sesquiterpene Dialdehyde Cinnamates from Pseudowintera axillaris

  摘要：

  Bioactivity-directed separation of a foliage extract from the New Zealand shrub Pseudowintera axillaris led to a compound with fungicidal activity against the plant pathogen Phytophthora infestans. This was identified as a new sesquiterpene dialdehyde cinnamate named paxidal. Two 6-hydroxy derivatives were present at lower levels in the extract. A further nine derivatives were synthesized from these natural products for a structure-activity study against a range of important food crop pathogens. The cinnamate group was important for fungicidal effects, and protection of the dialdehyde as a dimethyl acetal gave more potent, broader spectrum activity.

  DOI：

  10.1021/jf052585s

文献信息

• Fungicidal Sesquiterpene Dialdehyde Cinnamates from <i>Pseudowintera axillaris</i>
  作者：Nerida J. Brennan、Lesley Larsen、Stephen D. Lorimer、Nigel B. Perry、Eleanor L. Chapin、Todd L. Werk、Matthew J. Henry、Donald R. Hahn

  DOI：10.1021/jf052585s

  日期：2006.1.1

  Bioactivity-directed separation of a foliage extract from the New Zealand shrub Pseudowintera axillaris led to a compound with fungicidal activity against the plant pathogen Phytophthora infestans. This was identified as a new sesquiterpene dialdehyde cinnamate named paxidal. Two 6-hydroxy derivatives were present at lower levels in the extract. A further nine derivatives were synthesized from these natural products for a structure-activity study against a range of important food crop pathogens. The cinnamate group was important for fungicidal effects, and protection of the dialdehyde as a dimethyl acetal gave more potent, broader spectrum activity.