1-epi-cubenol | 81939-29-9

• 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: 1-epi-cubenol
• 英文别名: (+)-epicubenol；(+)-ent-epicubenol；epi-α-cubenol；(1R,4S,4aR,8aS)-4,7-dimethyl-1-propan-2-yl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-4a-ol
• CAS: 81939-29-9
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: COGPRPSWSKLKTF-GBJTYRQASA-N

物化性质

• 沸点：
  303.4±21.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)
• 保留指数：
  1623;1626;1618;1606;1623;1625;1616

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-epi-cubenol 在 吡啶 、 氯化亚砜 作用下， 反应 0.5h， 生成 cubenene
  参考文献：
  名称：

  (+)-Ent-epicubenol from the liverwort Scapania undulata

  摘要：

  DOI：

  10.1016/0031-9422(82)80055-1
• 作为产物：
  描述：

  farnesyl pyrophosphate 在 epicubenol synthase from Streptomyces sp. LL-B-7 、 magnesium chloride 作用下， 反应 2.0h， 生成 1-epi-cubenol
  参考文献：
  名称：

  Biosynthesis of (+)-epicubenol

  摘要：

  Incubation of [6-H-2]FPP (14a) with epicubenol synthase isolated from Streptomyces sp. LL-B7 gave epicubenol (1c) labeled at D-9 as established by 2H NMR. These results confirm the involvement of a predicted 1,2-hydride shift in the mechanism of formation of 1.

  DOI：

  10.1016/s0040-4039(00)73498-8

文献信息

• A Case of Convergent Evolution: The Bacterial Sesquiterpene Synthase for 1‐<i>epi</i>‐Cubenol from <i>Nonomuraea coxensis</i>
  作者：Jeroen S. Dickschat、Zhiyang Quan、Gregor Schnakenburg

  DOI：10.1002/cbic.202300581

  日期：2023.12

  A terpene synthase from Nonomuraea coxensis was identified as (+)‐1‐epi‐cubenol synthase. The enzyme is phylogenetically unrelated to the known enzyme of the same function that is widespread in streptomycetes. Isotopic labelling experiments were performed to unambiguously assign the NMR data and to investigate hydrogen migrations during terpene cyclisations. Epoxidations of (+)‐1‐epi‐cubenol and of the plant derived compounds (−)‐cubenol and (−)‐1‐epi‐cubenol confirmed the structure of a natural product isolated from the brown alga Dictyopteris divaricata and allowed to conclude on its absolute configuration. The crystal structures of the epoxides from (+)‐ and (−)‐1‐epi‐cubenol and the acid catalysed conversion into an isomeric ketone are reported.

  摘要 从 Nonomuraea coxensis 中鉴定出一种萜烯合成酶，即 (+)-1-epi-cubenol 合成酶。该酶在系统发育上与已知的广泛存在于链霉菌中的具有相同功能的酶无关。为了明确核磁共振数据的归属，并研究萜烯环化过程中的氢迁移，我们进行了同位素标记实验。(+)-1-epi-cubenol 的环氧化作用以及植物衍生化合物 (-)-cubenol 和 (-)-1-epi-cubenol 的环氧化作用证实了从褐藻 Dictyopteris divaricata 中分离出来的天然产物的结构，并得出了其绝对构型的结论。报告了 (+)- 和 (-)-1-epi-cubenol 环氧化物的晶体结构以及酸催化转化为异构酮的过程。
• Biosynthesis of (+)-cubenene and (+)-epicubenol by cell-free extracts of cultured cells of Heteroscyphus planus and cyclization of [2H]farnesyl diphosphates
  作者：Kensuke Nabeta、Kazuyoshi Kigure、Masaru Fujita、Tomomi Nagoya、Takehiro Ishikawa、Hiroshi Okuyama、Toshihide Takasawa

  DOI：10.1039/p19950001935

  日期：——

  The absolute stereochemistry of cubenene and epicubenol from cultured cells of Heteroscyphus planus was determined as both (+)-isomers by H-1 and C-13 NMR spectroscopy, GLC using a chiral capillary column, and optical rotations. Incubation of two geometrical isomers of deuteriated farnesyl diphosphate (FPP) with a cell-free extract from cultured cells indicated that both compounds were specifically formed from (2E,6E)-FPP. Gas-liquid chromatography-mass spectrometry (GLC-MS) and H-2 NMR analyses of(+)-cubenene and (+)-epicubenol generated from [1,1-H-2(2)]- and [6-H-2]-FPP confirmed the presence of 1,2- and 1,3-hydride shifts in their formation.
• Biosynthesis of (+)-epicubenol
  作者：David E. Cane、Manish Tandon

  DOI：10.1016/s0040-4039(00)73498-8

  日期：1994.7

  Incubation of [6-H-2]FPP (14a) with epicubenol synthase isolated from Streptomyces sp. LL-B7 gave epicubenol (1c) labeled at D-9 as established by 2H NMR. These results confirm the involvement of a predicted 1,2-hydride shift in the mechanism of formation of 1.
• (+)-Ent-epicubenol from the liverwort Scapania undulata
  作者：Joseph D. Connolly、William R. Phillips、Siegfried Huneck

  DOI：10.1016/0031-9422(82)80055-1

  日期：1982.1