methyl (1S,4aS,5S,8aR)-5-[(E)-2-(5,8-dimethoxynaphthalen-2-yl)ethenyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate | 949592-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (1S,4aS,5S,8aR)-5-[(E)-2-(5,8-dimethoxynaphthalen-2-yl)ethenyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 949592-38-5
• 化学式: C₂₉H₃₆O₄
• 分子量: 448.602
• InChiKey: JHRSADYIQPWSIK-DYMHJMOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl mirceocommunate 、 硫酸二甲酯 、 对苯醌 在 三氟化硼乙醚 、 sodium hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 乙醇 、 苯 为溶剂， 反应 24.5h， 以11%的产率得到methyl (1S,4aS,5S,8aR)-5-[(E)-2-(5,8-dimethoxynaphthalen-2-yl)ethenyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
  参考文献：
  名称：

  New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid

  摘要：

  Diterpenylquinone/hydroquinone derivatives were prepared through Diels-Alder cycloaddition between natural myrcecommunic acid or its methyl ester and p-benzoquinone (p-BQ), using BF3 center dot Et2O as catalyst or under microwave (Mw) irradiation. Acetyl, methyl and benzyl derivatives of several diterpenyinaplithohydroquinone were prepared from cycloadducts following two basic synthetic strategies, either protection before aromatisation or viceversa. Some of them were further functionalised at the B-ring of the decaline core. Most of the new compounds were evaluated and some of them resulted cytotoxic against several tumour cell lines with IC50 values tinder the mu M level. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.005