9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one

• 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: 9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one
• 英文别名: (+/-)-hydroxyatractylolide；atractylenolide III；(4aR,8aS,9aR)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: FBMORZZOJSDNRQ-BYCMXARLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one 在 CoCl(PPh₃)2 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.5h， 生成 (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione
  参考文献：
  名称：

  Biomimetic Synthesis of Biatractylolide and Biepiasterolide

  摘要：

  graphicThe biomimetic synthesis of the bisesquiterpenoids biatractylolide 1 and bieplasterolide 2 is reported.

  DOI：

  10.1021/ol035022f
• 作为产物：
  描述：

  苍术酮 在 air 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 858.5h， 生成 9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one
  参考文献：
  名称：

  Dimerization of Butenolide Structures. A Biomimetic Approach to the Dimeric Sesquiterpene Lactones (±)-Biatractylolide and (±)-Biepiasterolide

  摘要：

  The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

  DOI：

  10.1021/jo0488053

文献信息

• Regioselectivity of dimerisation of butenolides via captodative stabilised radicaloid intermediates
  作者：Sharanjeet K. Bagal、Robert M. Adlington、Rohan A.B. Brown、Jack E. Baldwin

  DOI：10.1016/j.tetlet.2005.04.125

  日期：2005.7

  The regioselective outcome observed during dimerisation of butenolides to dimeric structures via captodative stabilised radicaloids has been studied. The captodative stabilised radicaloids were generated by initial conversion of butenolides to chlorobutenolides via the corresponding hydroxybutenolides, followed by treatment with CoCl(PPh3)3.

  研究了在丁烯内酯通过capdodative稳定的基团二聚化为二聚体结构过程中观察到的区域选择性结果。通过将丁烯内酯通过相应的羟基丁烯内酯初步转化为氯丁烯内酯，然后用CoCl（PPh 3）3处理，生成了具有captodative稳定性的自由基。
• A general, concise, ‘collective’ approach to eudesmanolide sesquiterpenoids: total synthesis of bioactive atractylenolides I–IV and related natural products
  作者：Subburethinam Ramesh、Goverdhan Mehta

  DOI：10.1016/j.tetlet.2015.08.045

  日期：2015.10

  Total synthesis of seven bioactive atractylenolide-type eudesmanolides from Hagemann’s ester, following, a short, scalable, adaptable, and diversity oriented protocol, has been accomplished. This effort opens a gateway to access through synthesis an exceptionally potent and promising group of natural products and their congeners of contemporary interest.

  按照一个简短，可扩展，适应性强和面向多样性的方案，由哈格曼酯完成了七个生物活性白术内酯型大麦醇内酯的全合成。这项工作为通过合成获得一组异常有效和有前途的天然产物及其具有当代意义的同类产品打开了大门。