1,1-ethylenedioxy-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene | 131613-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-ethylenedioxy-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene
• 英文别名: 3,5,6,7,8,8a-Hexahydro-5,5,8a-trimethyl-1(2H)-naphthalinon-aethylenketal；4',4',8'a-trimethylspiro[1,3-dioxolane-2,8'-2,3,6,7-tetrahydro-1H-naphthalene]
• CAS: 131613-91-7
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: MHGHAUXYVXKHAW-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1-ethylenedioxy-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one
  参考文献：
  名称：

  烷基烯醇醚的二氯卡宾加合物作为呋喃的前体：在呋喃倍半萜烯（±）-pallescensin A的全合成中的应用

  摘要：

  从已知的反式-十氢萘酸酯2合成标题天然产物1时，已经采用了一种将呋喃环化成酮的新方法，其中涉及用碱处理衍生的甲基烯醇醚的二氯卡宾加合物。

  DOI：

  10.1016/j.tetlet.2006.07.068
• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 二乙二醇 为溶剂， 反应 4.0h， 生成 1,1-ethylenedioxy-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene
  参考文献：
  名称：

  Correction of the Structure of a New Sesquiterpene from Cistus creticus ssp. creticus

  摘要：

  In an attempt to identify the structure of a sesquiterpene from Cistus creticus ssp. creticus proposed in the literature as 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4alpha,5,8,8alpha-octahydronaphthalene, the synthesis of its cis isomer 2 was carried out in 11 steps and 9.5% yield. Comparison of the spectra of 2 and those reported earlier for the synthetic trans isomer 1 with the spectral profile of the isolated natural product indicated that the latter was not compatible with either 1 or 2. The correct structure was assigned, by detailed spectroscopic analysis of the natural product, as 6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (3).

  DOI：

  10.1021/np0498556

文献信息

• Dichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A
  作者：Jonathan S. Foot、Andrew T. Phillis、Phillip P. Sharp、Anthony C. Willis、Martin G. Banwell

  DOI：10.1016/j.tetlet.2006.07.068

  日期：2006.9

  A novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2.

  从已知的反式-十氢萘酸酯2合成标题天然产物1时，已经采用了一种将呋喃环化成酮的新方法，其中涉及用碱处理衍生的甲基烯醇醚的二氯卡宾加合物。
• Correction of the Structure of a New Sesquiterpene from <i>Cistus</i> <i>c</i><i>reticus</i> ssp. <i>c</i><i>reticus</i>
  作者：Konstantinos Hatzellis、Georgia Pagona、Apostolos Spyros、Costas Demetzos、Haralambos E. Katerinopoulos

  DOI：10.1021/np0498556

  日期：2004.12.1

  In an attempt to identify the structure of a sesquiterpene from Cistus creticus ssp. creticus proposed in the literature as 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4alpha,5,8,8alpha-octahydronaphthalene, the synthesis of its cis isomer 2 was carried out in 11 steps and 9.5% yield. Comparison of the spectra of 2 and those reported earlier for the synthetic trans isomer 1 with the spectral profile of the isolated natural product indicated that the latter was not compatible with either 1 or 2. The correct structure was assigned, by detailed spectroscopic analysis of the natural product, as 6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (3).