9-十八酮 | 18394-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 9-十八酮
• 英文名称: 9-octadecanone
• 英文别名: 9-octadecanal；octadecan-9-one；(Z)-9-octadecanal；Octadecan-9-on；Octyl-nonyl-keton
• CAS: 18394-00-8
• 化学式: C₁₈H₃₆O
• 分子量: 268.483
• InChiKey: RPUZRNKKZZATGV-UHFFFAOYSA-N

物化性质

• 熔点：
  51.5°C (estimate)
• 沸点：
  336.64°C (estimate)
• 密度：
  0.8453 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914190090

反应信息

• 作为反应物：
  描述：

  9-十八酮 在 lithium aluminium deuteride 作用下， 生成
  参考文献：
  名称：

  Enantiomeric Analysis of Homologous Series of Secondary Alcohols by Deuterium NMR Spectroscopy in a Chiral Nematic Liquid Crystal: Influence of Molecular Geometry on Chiral Discrimination

  摘要：

  NMR measurements of the differential ordering effect (DOE) are presented for homologous series of 22 chiral secondary aliphatic alcohols dissolved in a poly-(gamma-benzyl-L-glutamate) (PBLG)/dichloromethane liquid-crystalline solvent. The quadrupolar splittings of the solutes, which were deuterated at their chiral centres, were measured as a function of the PBLG concentration and temperature. The proton dipolar splittings of the dichloromethane in each sample were also measured and used as a reference. The results are analysed qualitatively in terms of the structures of the molecules and their asymmetric (or chiral) characteristics. Emphasis is put on comparative analysis of the chiral discrimination in members of each particular homologous series and on evaluating the Limits of the technique for molecules that have two very similar groups attached to their stereogenic centres.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1142::aid-chem1142>3.0.co;2-q
• 作为产物：
  描述：

  9-十八烯 在 zinc(II) iodide 、 2,3,4,5,6-五氯苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 9-十八酮
  参考文献：
  名称：

  由9,10-环氧十八烷和苯基异氰酸酯形成恶唑烷酮的研究

  摘要：

  AbstractThe formation of oxazolidone from 9,10‐epoxyoctadecane and phenylisocyanate was studied. One branch of epoxidized vegetable oil with one epoxy group per chain corresponds to 9,10‐epoxyoctadecane. This model could explain the probability of oxazolidone formation from natural oil‐derived epoxides. Epoxidized natural oils are TG consisting of glycerin and three FA with or without one to three epoxy groups in the middle of the chain. To study oxazolidone formation from an internal epoxy group without possible interference from the side reactions on the ester group, 9,10‐epoxyoctadecane was selected as the most appropriate model compound. Epoxy groups in the middle of allong aliphatic chain are of low reactivity toward isocyanates, and preparation of oxazolidones requires fairly harsh conditions such as high temperatures and catalysts, which also promote side reactions. The dominant side reaction is rearrangement of the epoxy groups. We found that the direction and magnitude of the rearrangement and the yield of any particular product depended on the catalyst used. Lithium chloride, aluminum trichloride, and zinc iodide catalyzed oxazolidone formation, along with the catalysis of side reactions such as ketone and carbonate formation. Aluminum trichloride showed the highest conversion of 9,10‐epoxyoctadecane to oxazolidone. Aluminum triisopropoxide, triphenylantimony iodide, and imidazole did not catalyze the formation of oxazolidone. They were effective as catalysts of epoxy group rearrangement and promoted the formation of hydroxyl, ketone, and carbonate compounds. Hydroxyl groups reacted with isocyanate to produce urethane.

  DOI：

  10.1007/s11746-003-0744-7

文献信息

• A General Approach to Intermolecular Olefin Hydroacylation through Light‐Induced HAT Initiation: An Efficient Synthesis of Long‐Chain Aliphatic Ketones and Functionalized Fatty Acids
  作者：Subhasis Paul、Joyram Guin

  DOI：10.1002/chem.202004946

  日期：2021.3

  hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.

  本文介绍了一种通过使用光诱导氢原子转移（HAT）引发对未活化底物进行分子间自由基加氢酰化的操作简单，对环境无害且有效的方法。使用可商购和廉价的光引发剂（Ph 2 CO和NHPI）使该方法具有吸引力。烯烃加氢酰化方案适用于多种带有许多官能团和许多复杂结构单元的底物。该反应证明是可扩展的（最大5 g）。可以使用该方案合成不同的官能化脂肪酸，石化产品和天然存在的烷烃。自由基链机制与该过程有关。
• Reductive couplings of acid chlorides mediated by SmI2
  作者：J. Collin、F. Dallemer、J.L. Namy、H.B. Kagan

  DOI：10.1016/s0040-4039(00)70710-6

  日期：1989.1

  Reductive couplings of acid chlorides and of acid chlorides with aldehydes or ketones in presence of an excess of SmI2 produce ketones in moderate to good yields.

  在过量的SmI 2的存在下，酰氯和酰氯与醛或酮的还原偶联以中等至良好的产率产生酮。
• Mild reduction of α-halo ketones to ketones promoted by PI3 or P2I4
  作者：J.N. Denis、A. Krief

  DOI：10.1016/s0040-4039(01)90341-7

  日期：1981.1

  PI3 and P2I4 clearly reduce α-bromo and α-iodo ketones

  PI 3和P 2 I 4明显还原α-溴和α-碘酮
• Production of Distillate Fuels from Biomass-Derived Polyoxygenates
  申请人：VIRENT, INC.

  公开号：US20130263498A1

  公开（公告）日：2013-10-10

  The present invention provides methods, reactor systems and catalysts for converting biomass and biomass-derived feedstocks to C 8+ hydrocarbons using heterogenous catalysts. The product stream may be separated and further processed for use in chemical applications, or as a neat fuel or a blending component in jet fuel and diesel fuel, or as heavy oils for lubricant and/or fuel oil applications.

  本发明提供了将生物质和生物质衍生原料转化为C8+烃的方法、反应器系统和催化剂，使用的是异质催化剂。产品流可以分离并进一步加工，用于化学应用，或作为纯净燃料或混合组分用于喷气燃料和柴油燃料，或作为润滑剂和/或燃油应用的重质油。
• CATALYSTS FOR HYDRODEOXYGENATION OF OXYGENATED HYDROCARBONS
  申请人：Blank Brian

  公开号：US20140051872A1

  公开（公告）日：2014-02-20

  The present invention provides catalysts, methods, and reactor systems for converting oxygenated hydrocarbons to oxygenated compounds. The invention includes methods for producing cyclic ethers, monooxygenates, dioxygenates, ketones, aldehydes, carboxylic acids, and alcohols from oxygenated hydrocarbons, such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like, using catalysts containing palladium, molybdenum, tin, and tungsten. The oxygenated compounds produced are useful in the production of liquid fuels, chemicals, and other products.

  本发明提供了将含氧碳氢化合物转化为含氧化合物的催化剂、方法和反应器系统。该发明包括利用含有钯、钼、锡和钨的催化剂从含氧碳氢化合物（如碳水化合物、糖类、糖醇、糖降解产物等）生产环氧醚、单氧化物、双氧化物、酮、醛、羧酸和醇的方法。生产的含氧化合物可用于生产液体燃料、化学品和其他产品。

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