achalensolide | 87302-42-9

• 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: achalensolide
• 英文别名: (3aR,5S,5aS,9aR)-5,8-dimethyl-1-methylidene-4,5,5a,6,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2,7-dione
• CAS: 87302-42-9
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: UQNONRHPSCIIJO-SKVKQCJPSA-N

物化性质

• 熔点：
  175-177 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• 沸点：
  446.3±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  achalensolide 在 manganese(IV) oxide 、 sodium tetrahydroborate 作用下， 生成 1-Epi-desoxy-geigerin
  参考文献：
  名称：

  Crystal structure and stereochemistry of achalensolide, a new guaianolide from Stevia achalensis

  摘要：

  DOI：

  10.1021/jo00170a033
• 作为产物：
  描述：

  (3R,7R,9S,10S)-12-(tert-butyldimethylsiloxy)-9,13-dimethyl-4-methylene-6-oxatricyclo[8.3.0.0^3,7]tetradec-13-en-5-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以81%的产率得到achalensolide
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y

文献信息

• Late‐stage Rh(II)‐catalyzed Nitrene Transfer for the Synthesis of Guaianolide Analogs with Enhanced Antiproliferative Activity
  作者：Sebastián J. Castro、José M. Padrón、Benjamin Darses、Viviana E. Nicotra、Philippe Dauban

  DOI：10.1002/ejoc.202100074

  日期：2021.3.26

  Application of rhodium(II)‐catalyzed intermolecular nitrene transfers to naturally‐occurring guaianolide compounds led to isolating nine new derivatives that possess an amino functional group at C‐1, C‐2, C‐10, C‐11, and/or C‐13 positions. The relevance of a late‐stage C−H amination strategy in medicinal chemistry is demonstrated by the improved antiproliferative activity of the C‐2 aminated analogs

  铑（II）催化的分子间氮烯转移到天然存在的愈创木酚内酯化合物上导致分离出9个在C-1，C-2，C-10，C-11和/或C处具有氨基官能团的新衍生物‐13个职位。新型C–H胺化策略在药物化学中的相关性由愈创木酚内酯产品的C–2胺化类似物的抗增殖活性提高证明。
• Guaiane sesquiterpenes from Decachaeta scabrella
  作者：Mahmut Miski、Doris H. de Luengo、Tom J. Mabry

  DOI：10.1016/s0031-9422(00)81511-3

  日期：1986.12

  Abstract From the dichloromethane extract of leaves of Decachaeta scabrella , in addition to three known guaianolides and two flavonoids, a new guaianolide, 11α, 13-dihydroxerantholide, and two new guaiane acids, pechueloic acid and 11,13-dihydropechueloic acid, were characterized. The structures of the new compounds were determined by spectral and chemical methods.

  摘要 从 Decachaeta scabrella 叶子的二氯甲烷提取物中，除了三种已知的愈创木酚内酯和两种黄酮类化合物外，还表征了一种新的愈创木酚内酯、11α, 13-二氢杂豆内酯和两种新的愈创木酸、pechueloic acid 和 11,13-dihydropechueloic acid。新化合物的结构是通过光谱和化学方法确定的。
• Castro, Victor; Ciccio, Francisco; Alvarado, Sandra, Liebigs Annalen der Chemie, 1983, # 6, p. 974 - 981
  作者：Castro, Victor、Ciccio, Francisco、Alvarado, Sandra、Bohlmann, Ferdinand、Schmeda-Hirschmann, Guillermo、Jakupovic, Jasmin

  DOI：——

  日期：——