Cyclohexanone, 2-(1-hydroxybutyl)- | 57548-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Cyclohexanone, 2-(1-hydroxybutyl)-
• 英文别名: 2-(1-hydroxybutyl)cyclohexan-1-one
• CAS: 57548-42-2
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: BATWHICBOTVWLT-UHFFFAOYSA-N

物化性质

• 沸点：
  280.0±13.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-环己烯氧基三甲基硅烷 在 盐酸 、 bismuth(III) chloride 、 zinc(II) iodide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Cyclohexanone, 2-(1-hydroxybutyl)-
  参考文献：
  名称：

  New effective catalysts for Mukaiyama-aldol and -Michael reactions: bismuth trichloride-metallic iodide systems

  摘要：

  Metallic iodide-activated bismuth(III) chloride efficiently catalyzes the Mukaiyama-Aldol and -Michael reactions. Some examples of reactions of silyl enol ethers derived from acetophenone and cyclohexanone (I and 2, respectively) with aldehydes, ketones, acetals, and alpha-enones are given. The cross-over aldolization between 1 and benzaldehyde in the presence of BiCl3-l.5ZnI2 or BiCl3-1.5SnI2 systems (5 % mol) has been carried out quantitatively at -30 and -78-degrees-C, respectively. For this reaction a similar activation has been also observed with antimony(III) chloride. X-ray patterns of catalytic systems show the formation of bismuth(III) iodide by CI/I-exchange reaction between BiCl3 and metallic iodide (NaI, ZnI2, SnI2,...). These results.have been rationalized with a two-step mechanism in which a key feature seems to be the activating role played by BiI3 toward the cleavage of the Bi-chelate intermediate by the chlorosilane formed. Ultrasound activates significantly the catalytic power of these metallic halide systems.

  DOI：

  10.1021/jo00059a040

文献信息

• Aldol reaction of trichlorotitanium enolates. Revaluation of the boat transition state
  作者：Eiichi Nakamura、Isao Kuwajima

  DOI：10.1016/s0040-4039(00)86265-6

  日期：1983.1

  The trichlorotitanium enolates generally undergo an erythro selective aldol reaction except one case which gives a threo aldol. A new form of the boat transition state has been proposed.

  三氯钛烯醇酸酯通常发生赤型选择性羟醛反应，除了一种情况下会产生苏式羟醛。已经提出了船过渡状态的新形式。
• Chemoselective aldol condensation in 5 mol dm−3 lithium perchlorate–nitromethane. A comparison with lithium perchlorate–diethyl ether medium
  作者：R. Sudha、S. Sankararaman

  DOI：10.1039/a900095j

  日期：——

  Aldol reactions of silyl enol ethers with aldehydes proceed in 5 mol dm–3 lithium perchlorate–nitromethane medium at ambient temperature. The reaction is highly chemoselective such that only aldehydes and cyclic ketones reacted while acyclic and aromatic ketones failed to react. The same reaction is not promoted in 5 mol dm–3 lithium perchlorate–diethyl ether medium. The difference between these two

  甲硅烷基烯醇醚与醛的醛醇缩合反应在环境温度为5 mol dm –3高氯酸锂–硝基甲烷的介质中进行。该反应是高度化学选择性的，使得仅醛和环状酮反应而无环和芳族酮不能反应。相同的反应不是在5摩尔分米促进-3的高氯酸锂-乙醚平台。两种介质之间的差异可通过与在乙醚中相比，在硝基甲烷中锂离子的路易斯酸酸度增加来解释。
• PROCESS FOR PRODUCING 2-ALKYLCYCLOALKANONE
  申请人：Kao Corporation

  公开号：EP2487150A1

  公开（公告）日：2012-08-15

  The present invention relates to a process for producing 2-alkylcycloalkanones with a high yield and a high purity. In addition, the present invention also relates to a process for producing lactones as a useful perfume material for cosmetics, flavors, etc. More specifically, the present invention relates to a process for producing a 2-alkylcycloalkanone represented by the following general formula (2) which includes the step of subjecting a 2-(1-hydroxyalkyl)-cycloalkanone to dehydration and hydrogenation reaction in a flow of a hydrogen gas under a pressure of from 20 to 200 kPa (absolute pressure) in the presence of an acid and a platinum group metal catalyst; and a process for producing a lactone which includes the step of subjecting the 2-alkylcycloalkanone to oxidation reaction using a percarboxylic acid: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.

  本发明涉及一种以高产率和高纯度生产 2-烷基环烷酮的工艺。此外，本发明还涉及一种生产内酯的工艺，这种内酯是一种有用的香水材料，可用于化妆品、香精等。更具体地说，本发明涉及一种生产由以下通式（2）代表的 2-烷基环烷酮的工艺，该工艺包括以下步骤：在一种酸和一种铂族金属催化剂存在下，使 2-（1-羟基烷基）-环烷酮在压力为 20 至 200 kPa（绝对压力）的氢气流中进行脱水和氢化反应；以及一种生产内酯的工艺，其中包括使用过羧酸使 2-烷基环烷酮进行氧化反应的步骤： 其中n为1或2的整数；R1和R2各自独立地为氢原子或具有1至8个碳原子的烷基，但R1和R2可通过相邻的碳原子形成环。
• Reversal of Enantioselectivity in Aldol Reaction: New Data on Proline/γ-Alumina Organic–Inorganic Hybrid Catalysts
  作者：György Szőllősi、Mónika Fekete、András A. Gurka、Mihály Bartók

  DOI：10.1007/s10562-013-1177-1

  日期：2014.3

  We report new results on the aldol reactions between aldehydes of three different types (aromatic, aliphatic and cycloaliphatic) and acetone/cycloalkanones as reaction partners, driven by organic-inorganic hybrid catalyst Pro/gamma-Al2O3. In contrast to the homogeneous liquid-phase reaction, over Pro/gamma-Al2O3 reversal of the enantioselection in up to 20-40 % ee depending on the structure of the aldehyde was observed in reactions of acetone. Reversal of the ee in the presence of gamma-Al2O3 cannot be generalized, as it has only been observed for acetone among the ketones studied by us. It was proven using methods of a great variety such as ultrasonic irradiation, reuse measurements on used catalyst and the filtrate of the first reaction, measurements on the l-Pro-l-Pro(OH) dipeptide, studies using mixtures of l-Pro and d-Pro that the organic-inorganic hybrid catalyst Pro/gamma-Al2O3 formed in situ is responsible for reversal of the ee. In the reactions of cycloalkanones there is presumably competition between the liquid-phase and the surface reaction over Pro/gamma-Al2O3 with preference for the former. Based on these results a surface reaction pathway was proposed. Although, the ees obtained under heterogeneous catalytic conditions are low, further studies may lead to application of this unusual phenomenon for obtaining chiral heterogeneous catalysts suitable for the preparation of the desired enantiomer of a chiral compound using the same chiral source.
• Erythro selective aldol reaction of α-trichlorostannyl ketones
  作者：Eiichi Nakamura、Isao Kuwajima

  DOI：10.1016/s0040-4039(00)86266-8

  日期：1983.1