2-<(2,2-dimethylpropanoyl)oxy>cyclohexanone | 85664-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(2,2-dimethylpropanoyl)oxy>cyclohexanone
• 英文别名: 2-pivaloyloxycyclohexanone；(2-Oxocyclohexyl) 2,2-dimethylpropanoate
• CAS: 85664-72-8
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: AXGGCABUWURZRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基乙酸 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 19.33h， 生成 2-<(2,2-dimethylpropanoyl)oxy>cyclohexanone
  参考文献：
  名称：

  Asymmetric α-oxyacylation of cyclic ketones

  摘要：

  环酮与手性N-烷基-O-酰基羟胺的反应可生成相应的α-氧酰基羰基化合物，其对映体过量率达89%。不对称诱导的水平受到溶剂极性、酸强度以及温度（影响较小）的影响。增加羟胺试剂中氮原子周围的立体障碍，可提高不对称诱导的水平，但这也会对转化反应的产率产生不利影响。通过对N-和O-取代基以及底物的考察，揭示了该方法的应用范围和局限性。

  DOI：

  10.1039/c2ob25293g

文献信息

• Visible light-assisted organocatalytic α-acyloxylation of ketones using carboxylic acids and <i>N</i>-halosuccinimides
  作者：Nagaraju Sakkani、Dhiraj K. Jha、Emily Whatley、John C.-G. Zhao

  DOI：10.1039/d2cc04016f

  日期：——

  many important pharmaceuticals and biologically active natural products and their derivatives. In this manuscript, the direct synthesis of α-acyloxylketones from ketones and readily available carboxylic acids was realized using a photo-assisted halogen bond-mediated organocatalytic α-acyloxylation reaction. The desired α-acyloxylation products were obtained in good to high yields.

  α-酰氧基羰基基序可以在许多重要的药物和具有生物活性的天然产物及其衍生物中找到。在这份手稿中，使用光辅助卤素键介导的有机催化 α-酰氧基化反应实现了从酮和容易获得的羧酸直接合成 α-酰氧基酮。以良好至高产率获得所需的 α-酰氧基化产物。
• α-Acyloxylation of Ketones/Cyclic Ethers Mediated by Hypervalent Iodine(III) Reagents as Oxidants and Nucleophilic Sources
  作者：Hao Jia、Nan Li、Chunmei Tang、Wenjing Ni、Xinru Zhao、Jing Sun、Fufang Wu、Xiaobao Shen、Hongbin Zhai

  DOI：10.1021/acs.joc.3c02526

  日期：2024.2.2

  This study describes a catalyst-free α-acyloxylation of ketones and a KBr-mediated α-acyloxylation of cyclic ethers. These conversions are effectively mediated by hypervalent iodine(III) reagents serving dual roles as the oxidant and nucleophilic source. Consequently, esters are produced directly in moderate to excellent yields. The proposed method features good functional group compatibility, a broad

  本研究描述了酮的无催化剂 α-酰氧基化和 KBr 介导的环醚 α-酰氧基化。这些转化由具有氧化剂和亲核源双重作用的高价碘 (III) 试剂有效介导。因此，可以直接以中等至优异的产率生产酯。该方法具有官能团兼容性好、底物范围广、合成效率高、环境友好等特点。
• .alpha.-Oxygenation of aldehydes and cyclic ketones by acylation-rearrangement of nitrones
  作者：Clark H. Cummins、Robert M. Coates

  DOI：10.1021/jo00160a027

  日期：1983.6
• A General Method for the α-Acyloxylation of Carbonyl Compounds
  作者：Cory S. Beshara、Adrian Hall、Robert L. Jenkins、Kerri L. Jones、Teyrnon C. Jones、Niall M. Killeen、Paul H. Taylor、Stephen P. Thomas、Nicholas C. O. Tomkinson

  DOI：10.1021/ol052474e

  日期：2005.12.1

  A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.
• CUMMINS, C. H.;COATES, R. M., J. ORG. CHEM., 1983, 48, N 12, 2070-2076
  作者：CUMMINS, C. H.、COATES, R. M.

  DOI：——

  日期：——