4-羟基-3-甲基-己烷-2-酮 | 116530-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-3-甲基-己烷-2-酮
• 英文名称: 4-hydroxy-3-methyl-2-hexanone
• 英文别名: 4-hydroxy-3-methyl-hexan-2-one；4-Hydroxy-3-methyl-hexan-2-on；3-Methyl-hexanol-(4)-on-(2)；4-Hydroxy-3-methylhexan-2-one
• CAS: 116530-49-5
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: KOFQZZHOSWGVHP-UHFFFAOYSA-N

物化性质

• 沸点：
  94-96 °C(Press: 20 Torr)
• 密度：
  0.939 g/cm3(Temp: 22 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-羟基-3-甲基-己烷-2-酮 在 sodium hypochlorite 、 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl 、 碳酸氢钠 、 potassium bromide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 3-methyl-2,4-hexanedione
  参考文献：
  名称：

  New Oxidation of β-Hydroxy α-Methyl Ketones:  A Convenient Synthesis of 3-Methylalkane-2,4-diones

  摘要：

  The synthesis of 3-methylalkane-2,4-diones, which are intense strawlike and fruit-flavored compounds, has been performed by the aldol condensation of n-alkanal (C2-C7) and methyl ethyl ketone to give 4-hydroxy-3-methyl-2-alkanones in 31-72% yield, followed by oxidation using sodium hypochlorite in the presence of 4-benzoyloxy-2,2,6,6-tetramethyl-piperidine-N-oxide in 60-86% yield.

  DOI：

  10.1021/op020029i
• 作为产物：
  描述：

  3-methyl-2,4-hexanediol 在 N-羟基邻苯二甲酰亚胺 、 cobalt(III) acetylacetonate 、 氧气 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以73%的产率得到4-羟基-3-甲基-己烷-2-酮
  参考文献：
  名称：

  Aerobic Oxidation of Alcohols to Carbonyl Compounds Catalyzed by N-Hydroxyphthalimide (NHPI) Combined with Co(acac)3

  摘要：

  Aerobic oxidation of various alcohols has been accomplished by using a new catalytic system, N-hydroxyphthalimide (NHPI) combined with Co(acac)(3). The oxidation of alcohols by NHPI was found to be markedly enhanced by adding a slight amount of Co(acac)(3) (0.05 equiv. to NHPI). Thus, secondary alcohols and vic-diols which are difficult to be oxidized by NHPI alone were smoothly oxidized with molecular oxygen (1 atm) to the corresponding carbonyl compounds under relatively mild conditions (65 similar to 75 degrees C).

  DOI：

  10.1016/00404-0399(50)1431g-

文献信息

• [EN] ALPHA-HYDROGEN SUBSTITUTED NITROXYLS AND DERIVATIVES THEREOF AS CATALYSTS<br/>[FR] NITROXYLES À SUBSTITUTION ALPHA-HYDROGÈNE ET LEURS DÉRIVÉS EN TANT QUE CATALYSEURS
  申请人：TECHNION RES & DEV FOUNDATION

  公开号：WO2013118118A1

  公开（公告）日：2013-08-15

  The present invention relates to novel alpha-hydrogen substituted nitroxyl compounds and their corresponding oxidized (oxoammonium cations) and reduced (hydroxylamine) forms, and to the use of such compounds, inter alia, for (1) oxidation of primary and secondary alcohols to aldehydes and ketones, respectively; (2) resolution of racemic alcohols; (3) desymmetrization of meso-alcohol; (4) as radicals and spin trapping reagents; and (5) as polymerization agents. The present invention further relates to processes for preparing the novel nitroxyl/oxoammonium/ hydroxylamine compounds from the corresponding amines, and to certain novel amine derivatives and their uses. The compounds of the invention as well as the amine precursors are also useful as ligands for transition metals and as organocatalysts in e.g., aldol reactions.

  本发明涉及新型α-氢取代亚硝基化合物及其相应的氧化物（氧化氨阳离子）和还原物（羟胺）形式的使用，其中这些化合物可用于（1）将一级和二级醇氧化为醛和酮；（2）拆分外消旋醇；（3）去对称化中性醇；（4）作为自由基和自旋捕获试剂；以及（5）作为聚合剂。本发明还涉及从相应胺制备新型亚硝基/氧化氨/羟胺化合物的方法，以及某些新型胺衍生物及其用途。本发明的化合物以及胺前体也可用作过渡金属的配体，并可用作有机催化剂，例如在Aldol反应中。
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