7-methyl-5-undecanone | 7127-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-methyl-5-undecanone
• 英文别名: 7-methylundecan-5-one；7-methyl-undecan-5-one
• CAS: 7127-23-3
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: AVEDPHRIFXICPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-己酮 在 氢气 作用下， 以 水 为溶剂， 349.84 ℃ 、500.01 kPa 条件下， 生成 7-methyl-5-undecanone
  参考文献：
  名称：

  Vapour-phase C–C coupling reactions of biomass-derived oxygenates over Pd/CeZrOx catalysts

  摘要：

  Studies of aldol condensation/hydrogenation reactions of 2-hexanone were carried out over Pd/CeZrOx and CeZrOx catalysts at temperatures between 573 and 673 K, and pressures of 5-26 bar. These studies were formulated to address the catalytic upgrading to transportation fuels of the mono-functional oxygenated compounds (consisting primarily of C-4-C-6 ketones, alcohols, carboxylic acids and heterocyclics) formed by the catalytic conversion of polyols over a Pt-Re/C catalyst. Characterization by XRD, TPR and NH3/CO2-TPD showed that Pd/CeZrOx catalyst consists of a partially reducible solid solution of cerium and zirconium oxides, and possesses both acidic and basic functionalities. Reaction kinetics studies show that in addition to the expected C-12 condensation product (7-methyl-5-undecanone), the CeZrOx-based catalysts produce C-18 and C-9 secondary species, along with light alkanes (<= C-7). Low loadings of Pd (e.g., 0.25 wt%) lead to optimal activity and selectivity for the production of C12 species. The high apparent activation energy of the formation of C-9 (140 kJ/mol) compared to the formation of C-12 and C-18 species (15 and 28 kJ/mol, respectively) indicates that these species may be formed as a result of the decomposition of heavier condensation products. The self-coupling of 2-hexanone was found to be positive order in both 2-hexanone and hydrogen. The addition of primary alcohols and carboxylic acids as well as water and CO2 to the feed was found to reversibly inhibit the self-coupling activity of 2-hexanone. This inhibition is strongest in the presence of CO2, and TPSR studies indicate that CO2 is removed from the surface by conversion to CO in the presence of reduced ceria species. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2009.06.014

文献信息

• Self-coupling of secondary alcohols by Ni/CeO2 catalyst
  作者：Katsuya Shimura、Kenichi Kon、S.M.A. Hakim Siddiki、Ken-ichi Shimizu

  DOI：10.1016/j.apcata.2013.04.040

  日期：2013.7

  heterogeneous catalytic system for the self-coupling of secondary alcohols under mild conditions. Effects of support material and oxidation state of Ni on the activity are studied and it is found that both CeO2 and metallic Ni are indispensable for the reaction. A possible reaction mechanism is proposed, in which ketones, formed by dehydrogenation of alcohol, undergone Aldol condensation to give α,β-unsaturated

  研究了负载型镍催化剂在N 2气氛下无添加剂条件下脂族仲醇的液相C C自偶联。在各种Ni催化剂中，在H 2中预先还原的1或3 wt％Ni / CeO 2催化剂显示1-辛醇在130°C时自偶合的二聚产物（较高的酮）收率最高（94％）。 ，并且催化剂被重复使用。该催化剂对于各种仲醇的自偶联也是有效的，为温和条件下仲醇的自偶联提供了第一个非均相催化体系。研究了载体材料和Ni的氧化态对活性的影响，发现CeO 2金属镍对于该反应是必不可少的。提出了一种可能的反应机理，其中将由醇脱氢形成的酮进行醛醇缩合反应，生成α，β-不饱和酮，最后将其通过原位形成的Ni H物种进行氢化。
• [EN] METHODS FOR PRODUCING CYCLIC AND ACYCLIC KETONES<br/>[FR] PROCÉDÉS DE PRODUCTION DE CÉTONES CYCLIQUES ET ACYCLIQUES
  申请人：UNIV CALIFORNIA

  公开号：WO2015148412A3

  公开（公告）日：2015-11-19
• Ruthenium-Catalyzed Self-Coupling of Primary and Secondary Alcohols with the Liberation of Dihydrogen
  作者：Ilya S. Makarov、Robert Madsen

  DOI：10.1021/jo4008699

  日期：2013.7.5

  The dehydrogenative self-condensation of primary and secondary alcohols has been studied in the presence of RuCl2(IiPr)(p-cymene). The conversion of primary alcohols into esters has been further optimized by using magnesium nitride as an additive, which allows the reaction to take place at a temperature and catalyst loading lower than those described previously. Secondary alcohols were dimerized into racemic ketones by a dehydrogenative Guerbet reaction with potassium hydroxide as the additive. The transformation gave good yields of the ketone diners with a range of alkan-2-ols, whereas more substituted secondary alcohols were unreactive. The reaction proceeds by dehydrogenation to the ketone, followed by an aldol reaction and hydrogenation of the resulting enone.
• Munch-Petersen,J., Bulletin de la Societe Chimique de France, 1966, p. 471 - 480
  作者：Munch-Petersen,J.

  DOI：——

  日期：——
• Kindt-Larsen,T. et al., Acta Chemica Scandinavica (1947), 1963, vol. 17, # 5, p. 1426 - 1432
  作者：Kindt-Larsen,T. et al.

  DOI：——

  日期：——