pinane | 303801-38-9

• 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: pinane
• 英文别名: (1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane
• CAS: 303801-38-9
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: XOKSLPVRUOBDEW-NPPUSCPJSA-N

物化性质

• 沸点：
  157.0±7.0 °C(Predicted)
• 密度：
  0.844±0.06 g/cm3(Predicted)
• 熔点：
  -53.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  pinane 在 氧气 、 cobalt(II) acetate 、 manganese(II) acetate 、 溴化铵 作用下， 以 氯苯 为溶剂， 反应 16.5h， 生成 3,6,6-三甲基双环-3,1,1-庚烷-2-酮 、 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 、 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 、 α-松油醇 、 isopinocamphone 、 (1alpha,2alpha,5alpha)-2,6,6-三甲基双环[3.1.1]庚烷-3-酮
  参考文献：
  名称：

  Transition-Metal Catalyzed Autoxidation of cis- and trans-Pinane to a Mixture of Diastereoisomeric Pinanols

  摘要：

  Autoxidations of the pinanes, obtained after hydrogenation of naturally occurring Pinus elliottii oil, were performed with or Without solvent, using the catalytic system Co(OAc)(2)/Mn(OAc)(2)/NH4Br in a 9:1:5 molar ratio, and dioxygen as the oxidant. The best selectivity for the pinanols was 71% (cis:trans ratio, 3:1) with 17% conversion. Autoxidations were also carried out in the absence of catalyst. The hydroperoxides formed with 17% conversion were decomposed with Na2SO3 and PPh3, resulting in 62% pinanols (cis:trans ratio, 5:1). The pyrolysis of the pinanols at 600 degrees C and a contact time of 1.15 x 10(-2) s/mol yielded 54% of linalool. The side products were mainly due to an ''ene'' reaction, giving diastereoisomeric 1,2-dimethyl-3-isopropenylcyclopentanols.

  DOI：

  10.1021/jf960472q
• 作为产物：
  描述：

  2-蒎烯聚合物 在 钌 作用下， 生成 pinane
  参考文献：
  名称：

  Hydrogenation of .alpha.-pinene to cis-pinane

  摘要：

  钌被发现是一种立体选择性催化剂，可用于将α-蒎烯氢化为顺式蒎烷。

  公开号：

  US04310714A1

文献信息

• Alkene Hydrogenations by Soluble Iron Nanocluster Catalysts
  作者：Tim N. Gieshoff、Uttam Chakraborty、Matteo Villa、Axel Jacobi von Wangelin

  DOI：10.1002/anie.201612548

  日期：2017.3.20

  sustainable synthesis. Alkene hydrogenations have so far been most effectively performed by noble metal catalysts. This study reports an iron‐catalyzed hydrogenation protocol for tri‐ and tetra‐substituted alkenes of unprecedented activity and scope under mild conditions (1–4 bar H2, 20 °C). Instructive snapshots at the interface of homogeneous and heterogeneous iron catalysis were recorded by the isolation

  贵金属技术的替代以及利用地球上丰富的金属实现新的反应性是可持续合成的核心。迄今为止，烯烃加氢最有效地是通过贵金属催化剂进行的。本研究报道了一种铁催化的三取代和四取代烯烃氢化方案，该方案在温和条件（1-4 bar H 2，20 °C）下具有前所未有的活性和范围。通过分离充当催化剂库和颗粒生长的可溶种子的新型铁纳米簇结构，记录了均相和非均相铁催化界面的指导性快照。
• Catalytic hydrogenation of olefins in biphasic water-liquid system
  作者：Chantal Larpent、René Dabard、Henri Patin

  DOI：10.1016/s0040-4039(00)95453-4

  日期：1987.1

  Cyclic and linear olefins and polyenes with or without functional groups are hydrogenated under very mild reaction conditions. Emphasis is put on the advantages of this method which requires no solvent and a water-soluble non air-sensitive catalyst.

  在非常温和的反应条件下将具有或不具有官能团的环状和线性烯烃和多烯氢化。强调了该方法的优点，该方法不需要溶剂和水溶性的非空气敏感性催化剂。
• Olefin-Stabilized Cobalt Nanoparticles for C=C, C=O, and C=N Hydrogenations
  作者：Sebastian Sandl、Felix Schwarzhuber、Simon Pöllath、Josef Zweck、Axel Jacobi von Wangelin

  DOI：10.1002/chem.201705366

  日期：2018.3.7

  hazardous reductants, special reaction conditions, and the formation of highly unstable pre‐catalysts. Reduction of CoBr2 with LiEt3BH in the presence of alkenes led to the formation of hydrogenation catalysts that effected clean conversions of alkenes, carbonyls, imines, and heteroarenes at mild conditions (3 mol % cat., 2–10 bar H2, 20–80 °C). Poisoning studies and nanoparticle characterization by

  结合了易接近性和高选择性的钴催化剂的开发构成了在氢化反应中替代贵金属催化剂的有前途的方法。本报告介绍了一种用户友好的规程，避免了复杂的配体，危险的还原剂，特殊的反应条件以及高度不稳定的预催化剂的形成。在烯烃存在下用LiEt 3 BH还原CoBr 2导致形成加氢催化剂，该催化剂在温和条件下（3 mol％的催化剂，2-10 bar H 2，可实现烯烃，羰基，亚胺和杂芳烃的干净转化）20–80°C）。通过TEM，EDX和DLS进行的中毒研究和纳米颗粒表征支持了异位催化机制的概念。
• Fine-Bubble–Slug-Flow Hydrogenation of Multiple Bonds and Phenols
  作者：Nobuyuki Mase、Takuya Iio、Kohei Nagai、Tomoki Kozuka、Akhtar Mst Sammi、Kohei Sato、Tetsuo Narumi

  DOI：10.1055/s-0040-1705948

  日期：2020.12

  We describe a promising method for the continuous hydrogenation of alkenes or alkynes by using a newly developed fine-bubble generator. The fine-bubble-containing slug-flow system was up to 1.4 times more efficient than a conventional slug-flow method. When applied in the hydrogenation of phenols to the corresponding cyclohexanones, the fine bubble–slug-flow method suppressed over-reduction. As this

  我们描述了一种使用新开发的细气泡发生器连续氢化烯烃或炔烃的有前途的方法。含细气泡的段塞流系统的效率比传统的段塞流方法高 1.4 倍。当应用于苯酚加氢生成相应的环己酮时，细泡-段塞流法抑制了过度还原。由于该方法不需要使用过量气体，因此有望广泛应用于提高气体介导流动反应的效率。
• A Mild Radical Procedure for the Reduction of <i>B</i>-Alkylcatecholboranes to Alkanes
  作者：Davide Pozzi、Eoin M. Scanlan、Philippe Renaud

  DOI：10.1021/ja055691j

  日期：2005.10.1

  A mild radical-mediated reduction of organoboranes is reported. The reducing agent is methanol complexed by the Lewis acidic B-methoxycatecholborane.

  据报道，有机硼烷的轻度自由基介导的还原。还原剂是与路易斯酸性 B-甲氧基儿茶酚硼烷络合的甲醇。