(+/-)-trans-calamanene | 73209-42-4

• 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: (+/-)-trans-calamanene
• 英文别名: trans-calamenene；calamenene；(1S,4R)-1,6-dimethyl-4-propan-2-yl-1,2,3,4-tetrahydronaphthalene
• CAS: 73209-42-4
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: PGTJIOWQJWHTJJ-QWHCGFSZSA-N

物化性质

• 沸点：
  285.0±20.0 °C(Predicted)
• 密度：
  0.900±0.06 g/cm3(Predicted)
• LogP：
  6.227 (est)
• 保留指数：
  1508;1512;1510;1509;1511;1518;1515;1523;1495;1510;1511;1511;1511;1515;1514;1513;1524;1516;1505;1505;1514;1511;1505;1516;1517;1532;1507;1515;1514;1514;1510;1513;1509;1579;1505

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  magnesium,2-methylpentane,bromide 在 phosphorus pentoxide 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (+/-)-trans-calamanene
  参考文献：
  名称：

  Cyclization-rearrangement of alkylstyrenes. 1. A. 1-Phenyl-1-pentene and homologs. B. A short synthesis of calamenene

  摘要：

  DOI：

  10.1021/jo01298a053

文献信息

• Total Synthesis of (+)-Erogorgiaene Using Lithiation–Borylation Methodology, and Stereoselective Synthesis of Each of Its Diastereoisomers
  作者：Tim G. Elford、Stefan Nave、Ravindra P. Sonawane、Varinder K. Aggarwal

  DOI：10.1021/ja207869f

  日期：2011.10.26

  A short (8 steps) synthesis of (+)-erogorgiaene in 44% overall yield from p-methylacetophenone is described. Key steps include lithiation/borylation-protodeboronation to build up the molecule and control the stereochemistry at C1 and C4. The C11 stereochemistry was similarly set up by using lithiation/borylation methodology. The use of a mixed, unhindered borane in the lithiation/borylation reaction

  描述了从对甲基苯乙酮中以 44% 的总产率合成 (+)-erogorgiaene 的短（8 步）合成。关键步骤包括锂化/硼化-原去硼化以构建分子并控制 C1 和 C4 的立体化学。通过使用锂化/硼化方法类似地建立了 C11 立体化学。事实证明，在锂化/硼化反应中使用混合的、不受阻碍的硼烷对于四氢萘酮衍生的氨基甲酸酯控制 C4 立体化学反应的成功至关重要。试剂控制方法的力量在 (+)-erogorgiaene 的所有非对映异构体的立体控制合成中得到了说明。
• Sesquiterpene constituents from the essential oil of the liverwort Plagiochila asplenioides
  作者：Adewale Martins Adio、Wilfried A. König

  DOI：10.1016/j.phytochem.2005.01.015

  日期：2005.3

  The essential oil of the liverwort Plagiochila asplenioides from two different locations in Northern Germany were investigated by chromatographic and spectroscopic methods. Seven compounds were isolated by preparative gas chromatography (GC) and their structures investigated by mass spectrometry (MS), NMR techniques and chemical correlations in combination with enantioselective GC. In addition to known

  通过色谱法和光谱法研究了来自德国北部两个不同地点的地衣 Plagiochila asplenioides 的精油。通过制备型气相色谱 (GC) 分离出七种化合物，并通过质谱 (MS)、核磁共振技术和化学相关性结合对映选择性 GC 研究了它们的结构。除了已知成分，aromadendra-1(10),3-diene，两种芳香倍半萜烃，bisabola-1,3,5,7(14)-tetraene 和 bisabola-1,3,5,7-tetraene，三种除 ent-4-epi-maaliol 外，倍半萜醚、muurolan-4,7-peroxide、plagiochilines W 和 X 还首次被鉴定为天然化合物。
• Biotransformation of cubenene to 7-hydroxycalamenene in cultured cells of the liverwort, Heteroscyphus planus
  作者：Makoto Hashimoto、Reiko Hozumi、Masateru Yamamoto、Kensuke Nabeta

  DOI：10.1016/s0031-9422(98)00737-7

  日期：1999.6

  The biosynthesis of 7-hydroxycalamenene using suspension cultured cells of the liverwort, Heteroscyphus planus, is described. The biotransformation of cubenene, but not calamenene, to 7-hydroxycalamenene suggests that it is formed via hydroxylation of the methylene carbon between its unconjugated double bonds. Thus followed by oxidation, thereby explaining the formation of 7-hydroxycalamenene without

  描述了使用地草 Heteroscyphus planus 的悬浮培养细胞生物合成 7-羟基木瓜烯。苦木烯（而不是木瓜烯）生物转化为 7-羟基木瓜烯表明它是通过亚甲基碳在其非共轭双键之间的羟基化形成的。因此随后进行氧化，从而解释了 7-羟基木瓜烯的形成而不引起 NIH 位移。
• Cadinane-type sesquiterpenoids from the liverwort Scapania undulata
  作者：Fumihiro Nagashima、Keiko Suda、Yoshinori Asakawa

  DOI：10.1016/s0031-9422(00)90406-0

  日期：1994.11

  Abstract Three new cadinane-type sesquiterpenoids, (+)-4-muurolen-6α-ol, scapanol and ent-T-muurolol, were isolated from the liverwort Scapania undulata together with the previously known (+)-ent-epicubenol and phytol, and their structures determined by extensive NMR techniques.

  摘要 三种新的卡地烷型倍半萜类化合物 (+)-4-muurolen-6α-ol、scapanol 和 ent-T-muurolol 与先前已知的 (+)-ent-epicubenol 和 phytol 一起从苔草 Scapania undulata 中分离出来，以及它们的结构由广泛的核磁共振技术确定。
• Chemistry of Khusinol: A Sesquiterpenoid Isolated from Vetiver Oil
  作者：Urvashi Bhardwaj、K.K. Chahal、Ramandeep Kaur

  DOI：10.14233/ajchem.2016.20017

  日期：——

  Vetiver essential oil was obtained from roots of Vetiveria zizanioides by hydrodistillation method. The unique feature of oil is the presence of antipodal terpenoids of which khusinol may be mentioned as representative. Khusinol, a white crystalline solid (m.p. 87 °C) isolated by column chromatography from vetiver oil was subjected to chemical transformations to afford khusinol oxides, cadina-4a,10b-diol and trans-calamenene derivatives. The structures of khusinol and its derivatives were elucidated using spectroscopic techniques.

  香根草精油是通过水蒸气蒸馏法从香根草的根中提取的。这种精油的独特之处在于其中含有对映萜类化合物，其中以库辛醇为代表。库辛醇是一种白色结晶固体（熔点87°C），通过柱色谱法从香根草油中分离出来，经过化学转化后得到库辛醇氧化物、cadina-4a,10b-diol和反式-calamenene衍生物。库辛醇及其衍生物的结构通过光谱技术得以阐明。