十五烷-5-酮 | 92862-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十五烷-5-酮
• 英文名称: pentadecan-5-one
• 英文别名: Pentadecan-5-on；5-Pentadecanone
• CAS: 92862-23-2
• 化学式: C₁₅H₃₀O
• 分子量: 226.403
• InChiKey: NADMBULPSVEFAV-UHFFFAOYSA-N

物化性质

• 熔点：
  35.25°C (estimate)
• 沸点：
  293.03°C (estimate)
• 密度：
  0.8184 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  十五烷-5-酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 正十五烷
  参考文献：
  名称：

  通过光诱导的HAT引发分子间烯烃加氢酰化的一般方法：长链脂肪族酮和功能化脂肪酸的高效合成

  摘要：

  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。

  DOI：

  10.1002/chem.202004946
• 作为产物：
  描述：

  十一烷酰三甲基硅烷 在 四乙基对甲苯磺酸铵 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 0.08h， 生成 十五烷-5-酮
  参考文献：
  名称：

  Electrochemical oxidation of acylsilanes and their tosylhydrazones

  摘要：

  Oxidation potentials of acylsilanes were found to be much less positive than those of ketones and aldehydes. The effect of silicon is attributed to the rise of the HOMO level by the interaction between the C-Si sigma-orbital and the nonbonding p orbital of the carbonyl oxygen which in turn favors the electron transfer. Preparative electrochemical oxidation of acylsilanes proceeded smoothly, giving rise to facile cleavage of the C-Si bond and the introduction of nucleophiles such as alcohols, water, and carbamates onto the carbonyl carbon. Electrochemical properties of tosylhydrazones of acylsilanes were also investigated. A decrease in oxidation potential of tosylhydrazones caused by silyl substitution was found to be smaller than that for carbonyl compounds. Preparative electrochemical oxidation of tosylhydrazones of acylsilanes gave the corresponding nitriles with consumption of a catalytic amount of electricity.

  DOI：

  10.1021/jo00044a023

文献信息

• Ruthenium-catalyzed Isomerization of Alkenol into Alkanone in Water under Irradiation of Microwaves
  作者：Kenichi Ishibashi、Masaaki Takahashi、Yutaka Yokota、Koichiro Oshima、Seijiro Matsubara

  DOI：10.1246/cl.2005.664

  日期：2005.5

  Ruthenium catalyzed isomerization of alkenol into alkanone through a migration of C–C double bond was performed in water under irradiation of microwaves. When the reaction was performed in deuterium oxide instead of water, the trail of the migration was shown by H–D exchange reaction.

  在微波照射下，以铑为催化剂，通过C–C双键迁移过程，在水相中实现了烯醇向烷酮的异构化。当反应在重水而非普通水环境中进行时，通过H–D交换反应揭示了双键迁移的路径。
• Mild and direct conversion of esters to morpholine amides using diisobutyl(morpholino)aluminum: application to efficient one-pot synthesis of ketones and aldehydes from esters
  作者：Ah Ram Jeon、Min Eai Kim、Jae Kyo Park、Won Kyu Shin、Duk Keun An

  DOI：10.1016/j.tet.2014.03.045

  日期：2014.7

  Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83–95% yields and aldehydes quantitatively.

  吗啉酰胺中间体很容易通过各种酯与二异丁基（吗啉代）铝的氨解反应制得，它与有机锂和还原剂（DIBALH或LDBMA）反应，而无需分离氨解中间体，可以定量得到83-95％的酮和醛。
• Hydrogen transfer type oxidation of alcohols by rhodium and ruthenium catalyst under microwave irradiation
  作者：Masaaki Takahashi、Koichiro Oshima、Seijiro Matsubara

  DOI：10.1016/j.tetlet.2003.10.032

  日期：2003.12

  Secondary alcohols were converted into the corresponding ketones by methyl acrylate and rhodium catalyst efficiently under microwave irradiation. Treatment of primary alcohols with the same condition resulted in the recovery of the starting materials. Primary alcohols were converted into aldehydes by hydrogen transfer reaction using methyl vinyl ketone and ruthenium catalyst under microwave irradiation

  在微波辐射下，丙烯酸甲酯和铑催化剂可将仲醇有效转化为相应的酮。在相同条件下处理伯醇会导致原料的回收。在微波辐射下，使用甲基乙烯基酮和钌催化剂通过氢转移反应将伯醇转化为醛。
• An effective one-pot conversion of acid chlorides to aldehydes and ketones
  作者：Jae Kyo Park、Won Kyu Shin、Duk Keun An

  DOI：10.1016/j.tetlet.2013.04.041

  日期：2013.6

  Aldehydes and ketones were synthesized from their respective acid chlorides via a one-pot protocol. Morpholine amide intermediates that were readily prepared by the aminolysis of various acid chlorides with diisobutyl(morpholino)aluminum smoothly reacted with the reducing agent LDBMA and the organolithium reagents under mild reaction conditions (0 °C), giving almost excellent product yields of up to

  通过一锅法从各自的酰氯合成醛和酮。在各种温和的反应条件下（0°C），通过各种酰氯与二异丁基（吗啉代）铝的氨解反应容易制备的吗啉酰胺中间体可与还原剂LDBMA和有机锂试剂平稳地反应，从而获得高达95的几乎优异的产品收率％。
• Chemoselective Conversion of Conjugated Nitroalkenes into Ketones by Sodium Borohydride-Hydrogen Peroxide: A New Synthesis of 4-Oxoalkanoic Acids, Dihydrojasmone and (±)-<i>exo</i>-Brevicomin
  作者：Roberto Ballini、Giovanna Bosica

  DOI：10.1055/s-1994-25557

  日期：——

  A new, simple, cheap, and practical procedure for the direct transformation of α,β-unsaturated nitroalkenes into ketones has been realized by the NaBH4/H2O2 system. By this method, other functional groups such as C-C double bonds, ketals or aromatic nitro groups were preserved. Application of this methodology to the preparation of 4-oxoalkanoic acids, dihydrojasmone, and (±)-exo-brevicomin is also reported.

  通过 NaBH4/H2O2 系统实现了一种新的、简单、廉价和实用的δ,δ-不饱和硝基烯烃直接转化为酮的过程。通过这种方法，C-C 双键、酮或芳香族硝基等其他官能团得以保留。此外，还报道了应用这种方法制备 4-氧代烷酸、二氢茉莉酮和 (±)-exo-brevicomin 的情况。

表征谱图