(3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylenedecahydronaphtho[1,2-b]furan-2(3H)-one | 1058170-20-9

• 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: (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylenedecahydronaphtho[1,2-b]furan-2(3H)-one
• 英文别名: (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
• CAS: 1058170-20-9
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: OCZYALGLUPTEFV-JHZZJYKESA-N

物化性质

• 沸点：
  382.4±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylenedecahydronaphtho[1,2-b]furan-2(3H)-one 在 臭氧 作用下， 以 氯仿 为溶剂， -78.0 ℃ 、2.53 MPa 条件下， 生成 (3'R,3'aS,5'aR,9'aS,9'bS)-3'-(methoxymethyl)-5'a-methylspiro[1,2,4-trioxolane-3,9'-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran]-2'-one
  参考文献：
  名称：

  A new sesquiterpene lactone from the roots of Saussurea lappa: Structure–anticancer activity study

  摘要：

  The dried roots of Saussurea lappa, called costus roots, are used in the traditional system of medicine for the treatment of cancer. In our investigation for the anticancer constituents from the hexane extract of this plant, a new sesquiterpene (1) was isolated along with the known compounds costunolide ( 2), beta-cyclocostunolide (3), dihydro costunolide (4) and dehydro costuslactone (5). Their structures were established by the extensive spectroscopic analyses. In addition, costunolide and beta-cyclocostunolide derivatives were synthesized using Michael-type addition reaction of NaOMe to the alpha-methylene-gamma-lactone moiety. All the compounds were tested for their in vitro cytotoxic activity. Compound 1 exhibited potent cytotoxic activity and other compounds displayed moderate activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.008
• 作为产物：
  描述：

  木香烃内酯 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylenedecahydronaphtho[1,2-b]furan-2(3H)-one 、 (3S,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylenedecahydronaphtho[1,2-b]furan-2(3H)-one
  参考文献：
  名称：

  容易获得倍半萜内酯的烷氧基，氨基，氨基甲酰基，羟基和硫醇衍生物及其对寄生杂草的生物活性评估

  摘要：

  假设倍半萜内酯的α-亚甲基-γ-内酯部分是其生物活性的关键单元。结果，这些化合物的修饰集中在该片段上。在本文报道的工作中，选择了两个倍半萜烯内酯，即脱氢木香内酯和β-环木香烯内酯，这是通过木香内酯的受控环化获得的一种马地内酯，通过在C-13处的迈克尔加成进行修饰。将此反应应用于两种化合物时，可以引入官能团烷氧基，氨基，氨基甲酰基，羟基和硫醇，以高至高收率得到产物，具体取决于所用的碱和溶剂。特别是，两种化合物都在C-13处引入了硫醇基，收率很高（> 90％），这对于这些倍半萜内酯是前所未有的。Orobanche cumana和Phelipanche ramosa。讨论了构效关系。

  DOI：

  10.1021/acs.jafc.9b03098

文献信息

• Easy Access to Alkoxy, Amino, Carbamoyl, Hydroxy, and Thiol Derivatives of Sesquiterpene Lactones and Evaluation of Their Bioactivity on Parasitic Weeds
  作者：Antonio Cala、Jesús G. Zorrilla、Carlos Rial、José M. G. Molinillo、Rosa M. Varela、Francisco A. Macías

  DOI：10.1021/acs.jafc.9b03098

  日期：2019.9.25

  C-13. On applying this reaction to both compounds, it was possible to introduce the functional groups alkoxy, amino, carbamoyl, hydroxy, and thiol to give products in good to high yields, depending on the base and solvent employed. In particular, the introduction of a thiol group at C-13 in both compounds was achieved with outstanding yields (>90%) and this is unprecedented for these sesquiterpene lactones

  假设倍半萜内酯的α-亚甲基-γ-内酯部分是其生物活性的关键单元。结果，这些化合物的修饰集中在该片段上。在本文报道的工作中，选择了两个倍半萜烯内酯，即脱氢木香内酯和β-环木香烯内酯，这是通过木香内酯的受控环化获得的一种马地内酯，通过在C-13处的迈克尔加成进行修饰。将此反应应用于两种化合物时，可以引入官能团烷氧基，氨基，氨基甲酰基，羟基和硫醇，以高至高收率得到产物，具体取决于所用的碱和溶剂。特别是，两种化合物都在C-13处引入了硫醇基，收率很高（> 90％），这对于这些倍半萜内酯是前所未有的。Orobanche cumana和Phelipanche ramosa。讨论了构效关系。
• A new sesquiterpene lactone from the roots of Saussurea lappa: Structure–anticancer activity study
  作者：A. Robinson、T. Vijay Kumar、E. Sreedhar、V.G.M. Naidu、Sistla Rama Krishna、K. Suresh Babu、P.V. Srinivas、J. Madhusudana Rao

  DOI：10.1016/j.bmcl.2008.06.008

  日期：2008.7

  The dried roots of Saussurea lappa, called costus roots, are used in the traditional system of medicine for the treatment of cancer. In our investigation for the anticancer constituents from the hexane extract of this plant, a new sesquiterpene (1) was isolated along with the known compounds costunolide ( 2), beta-cyclocostunolide (3), dihydro costunolide (4) and dehydro costuslactone (5). Their structures were established by the extensive spectroscopic analyses. In addition, costunolide and beta-cyclocostunolide derivatives were synthesized using Michael-type addition reaction of NaOMe to the alpha-methylene-gamma-lactone moiety. All the compounds were tested for their in vitro cytotoxic activity. Compound 1 exhibited potent cytotoxic activity and other compounds displayed moderate activity. (c) 2008 Elsevier Ltd. All rights reserved.