4-hydroxy-6-methylheptan-2-one | 359847-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-6-methylheptan-2-one
• CAS: 359847-21-5
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: ZVJYRWZHXCWWPC-UHFFFAOYSA-N

物化性质

• 沸点：
  219.5±13.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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-hydroxy-6-methylheptan-2-one 在 盐酸 作用下， 以 水 为溶剂， 以47.0 g的产率得到(3E)-6-甲基-3-庚烯-2-酮
  参考文献：
  名称：

  一种区域选择性醛醇缩合的新方案，可替代地方便地合成β-酮醇和α，β-不饱和酮。

  摘要：

  通过在水性介质中将β-酮酸与醛进行Knoevenagel缩合，可以实现β-酮醇和α，β-烯酮的常规合成。用10％的KOH水溶液将β-酮酸酯皂化，得到β-酮酸的钾盐，将其与醛在pH值为7.8-8.0的条件下于60摄氏度下原位缩合5-6小时。中间体β-酮羧酸酯在反应介质中平滑脱羧，从而以高收率（75-90％）得到β-酮醇。将反应混合物在pH 1下酸化并在剧烈搅拌下于70°C加热6小时，可直接生成相应的α，β-不饱和酮，收率良好（65-75％）。

  DOI：

  10.1021/jo0200872
• 作为产物：
  描述：

  2,6-Dimethyl-1-hepten-4-ol 在 臭氧 作用下， 以 甲醇 为溶剂， 反应 3.63h， 以90%的产率得到4-hydroxy-6-methylheptan-2-one
  参考文献：
  名称：

  Flow Ozonolysis Using a Semipermeable Teflon AF-2400 Membrane To Effect Gas−Liquid Contact

  摘要：

  A flow-through chemistry apparatus has been developed which allows gases and liquids to contact via a semipermeable Teflon AF-2400 membrane. In this preliminary investigation, the concept was proven by application to ozonolysis of a series of alkenes.

  DOI：

  10.1021/ol100322t

文献信息

• Improved Conditions for the Proline-Catalyzed Aldol Reaction of Acetone with Aliphatic Aldehydes
  作者：Benjamin List、Alberto Martínez、Kristina Zumbansen、Arno Döhring、Manuel van Gemmeren

  DOI：10.1055/s-0033-1340919

  日期：——

  The proline-catalyzed asymmetric aldol reaction between aliphatic aldehydes and acetone has, to date, remained underdeveloped. Challenges in controlling this reaction include avoiding undesired side reactions such as aldol condensation and self-aldolization. In recent years we have developed optimized conditions, which enable high yields and good to excellent enantioselectivities, and which are presented

  迄今为止，脯氨酸催化的脂肪醛和丙酮之间的不对称醛醇反应仍未得到充分发展。控制该反应的挑战包括避免不希望的副反应，例如醛醇缩合和自醛醇化。近年来，我们开发了优化条件，可实现高产率和良好的对映选择性，并在本通讯中进行了介绍。
• Processes for preparing beta-hydroxy-ketones and alpha,beta-unsaturated ketones
  申请人：Barnicki Donald Scott

  公开号：US20050004401A1

  公开（公告）日：2005-01-06

  Processes for producing β-hydroxy-ketones and α,β-unsaturated ketones are disclosed which comprise the crossed condensation of an aldehyde with a ketone in the presence of a hydroxide or alkoxide of alkali metal or an alkaline earth metal as catalyst. The products of the process, β-hydroxy-ketones and α,β-unsaturated ketones, are useful for the preparation of many commercially important products in the chemical process industries including solvents, drug intermediates, flavors and fragrances, other specialty chemical intermediates.

  披露了生产β-羟基酮和α,β-不饱和酮的过程，这些过程包括在碱金属或碱土金属的氢氧化物或醇盐的催化下，醛与酮的交叉缩合。该过程的产品，即β-羟基酮和α,β-不饱和酮，对于化学工艺工业中许多商业上重要产品的制备非常有用，包括溶剂、药物中间体、香精和香料、以及其他专用化学品中间体。
• Process for the production of 6-methylheptanone
  申请人：DEGUSA AG

  公开号：US20020128517A1

  公开（公告）日：2002-09-12

  Methylheptanone and corresponding homologous methylketones, in particular phytone and tetrahydrogeranyl acetone, are produced by aldol condensation of isovaleraldehyde or prenal or the corresponding aldehydes with acetone in the presence of a catalyst phase, which contains an aldolizing catalyst and a heterogeneous hydrogenating catalyst.

  甲基庚酮和对应的同系物甲基酮，特别是藤酮和四氢萜基乙酮，是通过异丙基醛或前醛或相应的醛与丙酮在存在催化剂相的情况下进行醛缩合反应而生产的，该催化相含有醛缩催化剂和异相氢化催化剂。
• Process for the preparation of 6-methylheptanone
  申请人：——

  公开号：US20030040645A1

  公开（公告）日：2003-02-27

  A process for the preparation of methylheptanone and corresponding homologous methyl ketones involves the cross-aldolization of acetone with the corresponding aldehyde. The polar catalyst phase is introduced with acetone and an organic auxiliary solvent phase to form a two phase mixture in the presence of hydrogen. The corresponding aldehyde is then added at temperatures between 40° C. and 200° C. The process can be run in a continuous manner with the polar catalyst phase being recyled after regeneration. The use of the non-polar auxiliary solvent(s) increase yield and selectivity.

  一种制备甲基庚酮及其相应同系物甲基酮的方法涉及丙酮与相应醛的交叉羟醛缩合反应。在氢气存在下，将极性催化剂相与丙酮和有机助溶剂相混合，形成两相混合物。随后在40°C至200°C的温度下加入相应的醛。该过程可以连续进行，极性催化剂相在再生后进行循环利用。使用非极性助溶剂可以提高产率和选择性。
• Reconstructed Hydrotalcite as a Highly Active Heterogeneous Base Catalyst for Carbon−Carbon Bond Formations in the Presence of Water
  作者：Kohki Ebitani、Ken Motokura、Kohsuke Mori、Tomoo Mizugaki、Kiyotomi Kaneda

  DOI：10.1021/jo060345l

  日期：2006.7.1

  reaction of carbonyl compounds is efficiently catalyzed by reconstructed hydrotalcites, obtained by treating the Mg−Al mixed oxide with water, as solid base catalysts in the presence of water. The catalysis of the reconstructed hydrotalcites is attributable to the surface base sites, created during the organization of the layered structure, with uniformly distributed strength. Furthermore, the reconstructed

  羰基化合物的醛醇缩合反应可通过重构水滑石有效催化，该水滑石是通过在水中存在的情况下将Mg-Al混合氧化物与水作为固体基础催化剂进行处理而获得的。重构的水滑石的催化归因于表面碱位，其在层状结构的组织期间产生，具有均匀分布的强度。此外，重建的水滑石提供了独特的酸碱双功能表面，能够促进腈与羰基化合物的Knoevenagel和Michael反应。