methyl 5-[2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate | 909297-15-0

• 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: methyl 5-[2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate
• 英文别名: (1S,4aR,5S,8aR)-5-[2-(2,5-Dimethoxy-2,5-dihydro-furan-3-yl)-ethyl]-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid methyl ester
• CAS: 909297-15-0
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: VRCWPAQOBJSOCP-KKSLKGIQSA-N

物化性质

• 沸点：
  463.8±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 5-[2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate 在 镍 氢气 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 0.25h， 生成 methyl 1,4a,6-trimethyl-5-[2-(1-methylpyrrol-3-yl)ethyl]decahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XIV. Synthesis of pyrrololabdanoids from lambertianic acid

  摘要：

  Treatment of lambertianic acid methyl ester with lead tetraacetate gave terpenoid 2,5-diacetoxydihydrofuran which reacted with primary amines to yield 3 -terpenyl -substituted pyrrol-2(5H)-ones; the reaction with bydrazine led to the corresponding pyridazine derivative. The obtained furanoterpenoids underwent oxidative methoxylation by the action of N-chlorobenzenesulfonamide or N-bromosuccinimide in methanol. 2,5-Dimethoxydihydrofurans thus formed were smoothly converted into 3-substituted furan-2(5H)-one in acid medium. Hydrogenation of 2,5-dimethoxydihydrofurans, followed by treatment with amines, gave 1,3-disubstituted pyrroles.

  DOI：

  10.1134/s1070428006060030
• 作为产物：
  描述：

  15,16-epoxylabda-8(17),13,14-trien-18-oic acid 在 chloramine-B 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 methyl 5-[2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Gram-scale synthesis of pinusolide and evaluation of its antileukemic potential

  摘要：

  Pinusolide (1), a known platelet-activating factor (PAF) receptor binding antagonist, was synthesized from lambertianic acid (2), a labdane-type diterpene readily accessible in multigram quantities from the Siberian pine tree. It was shown that 1 not only decreases the proliferation activity of tumor cells at relatively low concentrations but specifically induces apoptosis at 100 PM via the mitochondrial pathway in the Burkitt lymphoma cell line BJAB. Also, using primary lymphoblasts and leukemic cells from children with acute lymphoblastic leukemia (ALL) and acute myeloid leukemia (AML), a significant DNA fragmentation in pinusolide-treated cells could be detected in an ex vivo apoptosis assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.077