methyl (1S,4aS,8aR)-5-(2-{2-[2-(ethoxycarbonyl)-3-(trimethylsiloxy)buta-1,3-dien-1-yl]furan-3-yl}ethyl)-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate | 1392438-74-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: methyl (1S,4aS,8aR)-5-(2-{2-[2-(ethoxycarbonyl)-3-(trimethylsiloxy)buta-1,3-dien-1-yl]furan-3-yl}ethyl)-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate
• CAS: 1392438-74-2
• 化学式: C₃₁H₄₆O₆Si
• 分子量: 542.788
• InChiKey: FWFPCHJEFHTOQG-UPHHSBJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74.97
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-溴-6-甲基-p-苯醌 、 methyl (1S,4aS,8aR)-5-(2-{2-[2-(ethoxycarbonyl)-3-(trimethylsiloxy)buta-1,3-dien-1-yl]furan-3-yl}ethyl)-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate 在 L-脯氨酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以32%的产率得到methyl (1S,4aS,8aR)-5-{2-[2-(7-ethoxycarbonyl-6-hydroxy-2-methyl-1,4-dioxo-1,4-dihydronaphthalen-8-yl)furan-3-yl]ethyl}-1,4a,6-trimethyloctahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XXVIII. Diels-Alder reactions of 16-(trimethylsiloxybutadienyl) labdanoids

  摘要：

  15,16-Epoxy-16-(3-trimethylsiloxybuta-1,3-dien-1-yl)labdanoids were synthesized, and their reactions with cyclic dienophiles (1,4-benzoquinone, 1,4-toluquinone, 2-bromo-6-methyl-1,4-benzoquinone, and N-methylmaleimide) were studied. The reactions with unsymmetrically substituted benzoquinones were not selective. Methods for the preparation of hybrid compounds containing furan diterpenoid and substituted naphthoquinone, octahydroisoindoletrione, or hexahydroisoindoledione fragments were proposed.

  DOI：

  10.1134/s1070428012060164
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 哌啶 、 (1S,2S)-2-甲氨基-1-苯基丙-1-醇 、 溶剂黄146 、 三乙胺 、 zinc(II) chloride 作用下， 以 乙腈 、 苯 为溶剂， 反应 21.0h， 生成 methyl (1S,4aS,8aR)-5-(2-{2-[2-(ethoxycarbonyl)-3-(trimethylsiloxy)buta-1,3-dien-1-yl]furan-3-yl}ethyl)-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XXVIII. Diels-Alder reactions of 16-(trimethylsiloxybutadienyl) labdanoids

  摘要：

  15,16-Epoxy-16-(3-trimethylsiloxybuta-1,3-dien-1-yl)labdanoids were synthesized, and their reactions with cyclic dienophiles (1,4-benzoquinone, 1,4-toluquinone, 2-bromo-6-methyl-1,4-benzoquinone, and N-methylmaleimide) were studied. The reactions with unsymmetrically substituted benzoquinones were not selective. Methods for the preparation of hybrid compounds containing furan diterpenoid and substituted naphthoquinone, octahydroisoindoletrione, or hexahydroisoindoledione fragments were proposed.

  DOI：

  10.1134/s1070428012060164

文献信息

• Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent
  作者：M. E. Mironov、E. E. Shults

  DOI：10.1007/s11172-023-4047-z

  日期：2023.10

  5]undecane-1,5,9-triones by the l-proline catalyzed three-component Knoevenagel—Diels—Alder reaction of diterpenoid enone, aldehyde, and the Meldrum’s acid were proposed. A diterpenoid analog of anticancer agents with an 11-(biphenyl-4-yl)-2,4-di-oxaspiro[5.5]undecanone substituent was synthesized by the Suzuki reaction of the obtained bromophenyl-substituted spirocyclic ketone with 3,4,5-(trimethoxyphenyl)boronic

  16-(3-三甲基甲硅烷氧基丁二烯基)呋喃二环己烷类化合物与5-亚甲基(亚芳基)-3,3-二甲基-2,4-二恶烷-1,5-二酮或5-亚甲基(亚芳基)-1,3的Diels-Alder反应-二甲基嘧啶-2,4,6(1 H ,3 H ,5 H )-三酮在L-脯氨酸 href=https://www.molaid.com/MS_37224 target="_blank">氨酸存在下区域选择性地进行并产生7-呋喃萜基取代的3,3-二甲基-2,4-二氧杂螺[5.5 ]-十一烷-1,5,9-三酮或2,4-二甲基-2,4-二氮杂螺[5.5]十一烷-1,3,5,9-四酮。L-脯氨酸催化二萜烯酮、醛和Meldrum's三组分Knoevenagel-Diels-Alder反应一锅合成萜基取代的二氧杂螺-[5.5]十一烷-1,5,9-三酮的条件提出了酸。通过所得溴苯基取代螺环酮与 3,4,5 的 Suzuki 反应合成了具有 11-(联苯-4-基)-2,4-二氧杂螺[5.5]十一烷酮取代基的抗癌剂二萜类似物-(三甲氧基苯基)硼酸。