methyl mirceocommunate

• 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 mirceocommunate
• 英文别名: methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(3-methylidenepent-4-enyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: FHQUKAJSXNCFAA-ZSXPUABSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl mirceocommunate 在 sodium periodate 、 四氧化锇 、 sodium 作用下， 以 水 、 叔丁醇 为溶剂， 反应 160.0h， 生成 13-oxo-14,15-dinorlabd-8(17)-en-19-oic acid methyl ester
  参考文献：
  名称：

  Barrero, A. F.; Alvarez-Manzaneda, E. J.; Altarejos, J., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 700 - 707

  摘要：

  DOI：

文献信息

• New Selective Cytotoxic Diterpenylquinones and Diterpenylhydroquinones
  作者：José M Miguel del Corral、Marina Gordaliza、M Angeles Castro、M Mar Mahiques、Pablo Chamorro、Aurora Molinari、M Dolores García-Grávalos、Howard B. Broughton、Arturo San Feliciano

  DOI：10.1021/jm001048q

  日期：2001.4.1

  considered in relation to the cytotoxicity toward neoplastic cells and the selectivity of these diterpenylnaphthoquinones/hydroquinones and anthraquinones. Several compounds showed IC50 values under the micromolar level, and four of these derivatives were evaluated at the NCI screening panel. The results showed an important selectivity toward renal cancer lines, identifying these compounds as a very promising

  通过在三个拉丹二萜类化合物（肉豆蔻酸，甲基肉豆蔻酸甲酯和肉豆蔻酸乙酸酯）和对苯醌或1,4-萘醌之间的狄尔斯-阿尔德环加成反应制备了一系列新的二萜烯醌/对苯二酚。考虑到对肿瘤细胞的细胞毒性以及这些二萜烯基萘醌/对苯二酚和蒽醌的选择性，考虑了醌/对苯二酚片段和其他结构特征（如萜烯核中不同功能）的影响。几种化合物在微摩尔水平下显示出IC50值，在NCI筛选小组中评估了其中的四种衍生物。结果显示出对肾癌细胞系的重要选择性，将这些化合物鉴定为非常有希望的抗肿瘤药。
• 13C NMR data for labdane diterpenoids
  作者：Alejandro F. Barrero、Joaquin Altarejos

  DOI：10.1002/mrc.1260310317

  日期：1993.3

  The analysis of the 13C NMR spectra of 91 labdane‐type compounds, classified into ten different series, is reported.

  报告了 91 种拉丹型化合物的 13C NMR 谱分析，分为十个不同系列。
• Natural and thermal isomers of methyl trans-communate
  作者：P.W. Atkinson、W.D. Crow

  DOI：10.1016/s0040-4020(01)92769-3

  日期：1970.1

  A new diterpene acid, isolated as its methyl ester from Callitris columellaris F. Muell., is shown to be Δ13(17)-communic acid. Another new isomer of communic acid is shown to result from thermal rearrangement of trans-communic acid methyl ester on gas chromatography, and is tentatively assigned the structure methyl labda-8(14)-trans-11(12)-cis-13(15)-trien-19-oate on the basis of spectroscopic and

  从Callitris columellaris F. Muell。分离出的一种新的二萜烯酸为甲酯，显示为Δ13 （17）-交流酸。显示了另一种新的甲酸的异构体，是由反式-甲酸甲酯在气相色谱上的热重排产生的，并被暂定为甲基结构化甲基labda-8（14）-反式-11（12）-顺式-13（15） ）-trien-19-oate基于光谱和机械学考虑。
• An easy route to pentacyclic terpenylquinones
  作者：M. Angeles Castro、José M. Miguel del Corral、M. Lucena Rodríguez、Arturo San Feliciano

  DOI：10.1016/j.tetlet.2011.11.080

  日期：2012.2

  Cyclisation of terpenylnaphthohydroquinone derivatives or terpenylquinone cycloadducts, obtained from methyl myrcecommunate, was performed in the presence of HI, I-2 or BF3 center dot OEt2 and provides efficient synthetic strategies for the preparation of pentacyclic terpenylquinones. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.