dihydroisoparthenin | 28625-39-0

• 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: dihydroisoparthenin
• 英文别名: (6S,6aR,9aS,9bR)-6a-hydroxy-3,6,9a-trimethyl-4,5,6,7,8,9b-hexahydroazuleno[8,7-b]furan-2,9-dione
• CAS: 28625-39-0
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: AEVZZALQJYKVBB-VLBDWWMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dihydroisoparthenin 在 甲酸 作用下， 反应 9.0h， 以73%的产率得到anhydrodihydroisoparthenin
  参考文献：
  名称：

  Charminarone, a seco-pseudoguaianolide from Parthenium hysterophorus

  摘要：

  A novel sesquiterpenoid, charminarone, the first seco-pseudoguaianolide, has been isolated along with several known compounds from the whole plant of Parthenium hysterophorus. The structure of the new compound has been settled as 1,10-seco-dihydro-isoparthenin 1, 10-dione from its spectral data as well as from its conversion by reductive coupling reaction with Zn/TiCl4 reagent to the known compound, anhydrodihydroisoparthenin. The reagent Zn/TiCl4 has been used here for the first time to construct the seven membered ring of a pseudoguaianolide sesquiterpenoid. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00147-x
• 作为产物：
  描述：

  银胶菊宁 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以70%的产率得到dihydroisoparthenin
  参考文献：
  名称：

  Enantioselective synthesis of neoambrosin, parthenin, and dihydroisoparthenin

  摘要：

  Enantioselective synthesis of the titled ambrosanolides is described. Use of the trimethylsilyl group as an anchor contributed to the stereoselective introduction of two methyl groups.

  DOI：

  10.1016/0040-4020(95)00068-j

文献信息

• Occurrence of hysterin and dihydroisoparthenin in Parthenium hysterophorus
  作者：Anna K. Picman、Felipe Balza、G.H. Neil Towers

  DOI：10.1016/s0031-9422(82)85070-x

  日期：1982.1
• Enantioselective synthesis of neoambrosin, parthenin, and dihydroisoparthenin
  作者：Morio Asaoka、Taketoshi Ohkubo、Hirotsune Itahana、Takatoshi Kosaka、Hisashi Takei

  DOI：10.1016/0040-4020(95)00068-j

  日期：1995.3

  Enantioselective synthesis of the titled ambrosanolides is described. Use of the trimethylsilyl group as an anchor contributed to the stereoselective introduction of two methyl groups.
• Charminarone, a seco-pseudoguaianolide from Parthenium hysterophorus
  作者：B. Venkataiah、C. Ramesh、N. Ravindranath、Biswanath Das

  DOI：10.1016/s0031-9422(03)00147-x

  日期：2003.6

  A novel sesquiterpenoid, charminarone, the first seco-pseudoguaianolide, has been isolated along with several known compounds from the whole plant of Parthenium hysterophorus. The structure of the new compound has been settled as 1,10-seco-dihydro-isoparthenin 1, 10-dione from its spectral data as well as from its conversion by reductive coupling reaction with Zn/TiCl4 reagent to the known compound, anhydrodihydroisoparthenin. The reagent Zn/TiCl4 has been used here for the first time to construct the seven membered ring of a pseudoguaianolide sesquiterpenoid. (C) 2003 Elsevier Science Ltd. All rights reserved.