homodrimanic epoxide | 68804-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: homodrimanic epoxide
• 英文别名: 2-[(1aR,3aS,7aS,7bS)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]ethyl acetate
• CAS: 68804-46-6
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: SPSYTQBYLJXQJV-OWLYRPNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  homodrimanic epoxide 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以45%的产率得到(5S,8R,10S)-9-(2-acetoxyethyl)-austrodor-9-one
  参考文献：
  名称：

  Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid

  摘要：

  An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.024
• 作为产物：
  描述：

  2-[2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]ethyl acetate 在 吡啶 、 碘 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 homodrimanic epoxide
  参考文献：
  名称：

  Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid

  摘要：

  An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.024

文献信息

• Selectivity Control in Terpene Rearrangements: A Biomimetic Synthesis of the Halimanic Bicyclic Core
  作者：Tatiana Sîrbu、Vladilena Girbu、Petru Harghel、Vasile Rusu、Nicon Ungur、Veaceslav Kulciţki

  DOI：10.1055/s-0037-1610686

  日期：2019.5

  system. In particular, an acidic pillared clay selectively promoted this transformation. The bicyclic core of the halimanic framework is synthesized in optically active form by an acid-induced rearrangement of a homo­drimanic epoxide. The substrate can follow two different pathways under acidic treatment. Using fluorosulfonic acid as a promoter at low temperature favors ring contraction to a perhydrindanic

  抽象的 卤代骨架的双环核心是通过酸诱导的高锰酸环氧化物的旋光形式合成的。底物在酸性处理下可以遵循两种不同的途径。在低温下使用氟磺酸作为促进剂有利于环缩合为全氢茚满结构。相反，较高温度下的较弱酸主要导致甲基甲基迁移和卤代双环系统的形成。特别地，酸性带柱粘土选择性地促进了这种转变。 卤代骨架的双环核心是通过酸诱导的高锰酸环氧化物的旋光形式合成的。底物在酸性处理下可以遵循两种不同的途径。在低温下使用氟磺酸作为促进剂有利于环缩合为全氢茚满结构。相反，较高温度下的较弱酸主要导致甲基甲基迁移和卤代双环系统的形成。特别地，酸性带柱粘土选择性地促进了这种转变。
• Design, synthesis, and antimicrobial activity of some novel homodrimane sesquiterpenoids with diazine skeleton
  作者：Kaleria Kuchkova、Aculina Aricu、Elena Secara、Alic Barba、Pavel Vlad、Nicon Ungur、Cristina Tuchilus、Sergiu Shova、Gheorghita Zbancioc、Ionel I. Mangalagiu

  DOI：10.1007/s00044-013-0720-3

  日期：2014.3

  sesquiterpenoids with and without diazine skeleton has been evaluated. All the tested compounds have an excellent antibacterial activity against Gram-positive strains S. aureus and B. cereus. SAR correlations concerning antimicrobial activity are reported. Graphical AbstractThe design, synthesis, and in vitro antimicrobial activity of some novel homodrimane sesquiterpenoids with diazine skeleton are described

  摘要本文中，我们报告了关于一些具有二嗪骨架的新高等倍半萜类化合物的设计，合成和体外抗菌活性的可行研究。该反应途径是有效且直接的，包括将二嗪与带有酰氯或有机酸官能团的高锰酸二倍半萜类化合物直接进行N-酰化。给出了所获得化合物的可靠解释和可行的反应机理。已经评估了具有和不具有二嗪骨架的高同型倍半萜类化合物的体外抗菌活性。所有测试的化合物对革兰氏阳性菌株金黄色葡萄球菌和蜡状芽孢杆菌均具有优异的抗菌活性。报道了与抗菌活性有关的SAR相关性。 图形概要描述了一些具有二嗪骨架的新高同型倍半萜的设计，合成和体外抗菌活性。抗菌测试证明，一些高锰酸倍半萜具有出色的生物活性。
• Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid
  作者：Veaceslav Kulcitki、Nicon Ungur、Margherita Gavagnin、Marianna Carbone、Guido Cimino

  DOI：10.1016/j.tetasy.2003.10.024

  日期：2004.2

  An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.