methyl (1S,4aR,5R,7R,8aR)-5-[2-(5,8-dimethoxynaphthalen-2-yl)ethyl]-7-hydroxy-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate | 949592-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (1S,4aR,5R,7R,8aR)-5-[2-(5,8-dimethoxynaphthalen-2-yl)ethyl]-7-hydroxy-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 949592-51-2
• 化学式: C₂₉H₃₈O₅
• 分子量: 466.618
• InChiKey: VMDWODNGHZJIOY-RCUSWNFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1S,4aR,5R,7R,8aR)-5-[2-(5,8-dimethoxynaphthalen-2-yl)ethyl]-7-hydroxy-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以70%的产率得到methyl (1S,4aR,5R,8aR)-5-[2-(5,8-dimethoxynaphthalen-2-yl)ethyl]-1,4a-dimethyl-6-methylidene-7-oxo-2,3,4,5,8,8a-hexahydronaphthalene-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
• 作为产物：
  描述：

  methyl (1S,4aR,5S,8aR)-5-[2-(5,8-dimethoxynaphthalen-2-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以67%的产率得到methyl (1S,4aR,5R,7R,8aR)-5-[2-(5,8-dimethoxynaphthalen-2-yl)ethyl]-7-hydroxy-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

文献信息

• New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid
  作者：José M. Miguel del Corral、M. Angeles Castro、M. Lucena Rodrı´guez、Pablo Chamorro、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1016/j.bmc.2007.06.005

  日期：2007.9.1

  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.