1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4-(1-methylethyl)naphthalene | 16728-99-7

• 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: 1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4-(1-methylethyl)naphthalene
• 英文别名: cadina-1,4-diene；cubenene；4-isopropyl-1,6-dimethyl-1,2,3,4,4a,7-hexahydronaphthalene；trans-cadina-1,4-diene；naphthalene, 1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4-(1-methylethyl)-；1,6-dimethyl-4-(1-methylethyl)-(1,2,3,4,4a,7)hexahydronaphthalene；1,2,3,4,6,8a-hexahydro-1-isopropyl-4,7-dimethyl-naphthalene；1,6-dimethyl-4-propan-2-yl-1,2,3,4,4a,7-hexahydronaphthalene
• CAS: 16728-99-7
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: JUQGWBAOQUBVFP-UHFFFAOYSA-N

物化性质

• 沸点：
  279.2±15.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)
• 保留指数：
  1515;1546;1519

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-epi-cubenol 在 吡啶 、 氯化亚砜 作用下， 反应 0.5h， 生成 cubenene 、 1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4-(1-methylethyl)naphthalene
  参考文献：
  名称：

  Biosynthesis of (+)-cubenene and (+)-epicubenol by cell-free extracts of cultured cells of Heteroscyphus planus and cyclization of [2H]farnesyl diphosphates

  摘要：

  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.

  DOI：

  10.1039/p19950001935

文献信息

• 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.

表征谱图