2-oxocyclohexyl 4-methoxybenzoate | 61609-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-oxocyclohexyl 4-methoxybenzoate
• 英文别名: 2-Oxocyclohexyl 4-methoxybenzoate；(2-oxocyclohexyl) 4-methoxybenzoate
• CAS: 61609-23-2
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: VREDYHRDVQREKI-UHFFFAOYSA-N

物化性质

• 沸点：
  395.8±32.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-methyl-N-tert-butoxycarbonyl-O-(4-methoxybenzoyl)hydroxylamine 在 盐酸 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 2-oxocyclohexyl 4-methoxybenzoate
  参考文献：
  名称：

  A General Method for the α-Acyloxylation of Carbonyl Compounds

  摘要：

  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.

  DOI：

  10.1021/ol052474e

文献信息

• C O bond formation via oxidative-coupling pathway in eutectic mixture of choline chloride/urea as a green solvent
  作者：Dariush Saberi、Neda Manouchehri、Khodabakhsh Niknam

  DOI：10.1016/j.molliq.2018.12.046

  日期：2019.2

  CO bond formation between terminal alkenes/benzyl alcohols as an arylcarboxy surrogate and carbonyl compounds in a biodegradable deep eutectic solvent (DES) based on choline chloride and urea was performed. By employment of TBAI as catalyst and TBHP as oxidant, various derivatives of carbonyl compounds were benzylated in α position in good to high yield at 90 °C. Moreover, α-oxybenzoylation of diethyl

  在基于氯化胆碱和尿素的可生物降解的深共熔溶剂（DES）中，作为芳基羧基替代物的末端烯烃/苄醇与羰基化合物之间进行了C O键形成。通过使用TBAI作为催化剂和TBHP作为氧化剂，羰基化合物的各种衍生物在90℃下以良好或高产率在α位被苄基化。此外，在上述DES中，通过使用NaI作为催化剂和TBHP作为氧化剂，在上述DES中进行了丙二酸二乙酯与羧酸的α-氧基苯甲酰化反应。
• Microwave-Enhanced Coupling of Carboxylic Acids with Liquid Ketones and Cyclic Ethers Using Tetrabutylammonium Iodide/<i>t</i>-Butyl Hydroperoxide
  作者：Pablo Macías-Benítez、F. Javier Moreno-Dorado、Francisco M. Guerra

  DOI：10.1021/acs.joc.0c00519

  日期：2020.5.1

  The oxidative coupling of carboxylic acids with liquid ketones and cyclic ethers has been accomplished in minutes using t-butyl hydroperoxide in the presence of tetrabutylammonium iodide under microwave irradiation in the absence of a solvent. In addition to drastically shortening the reaction times, the use of microwaves resulted, in general, in yields equal to or higher than those obtained by conventional

  在叔丁基碘化铵存在下，在无溶剂的情况下，在微波辐射下，使用叔丁基氢过氧化物在几分钟之内完成了羧酸与液态酮和环醚的氧化偶联。除了大大缩短反应时间之外，使用微波通常还产生等于或高于通过常规加热获得的产率。
• The Bu4NI-catalyzed alfa-acyloxylation of ketones with benzylic alcohols
  作者：Songjin Guo、Jin-Tao Yu、Qiang Dai、Haitao Yang、Jiang Cheng

  DOI：10.1039/c4cc01652a

  日期：——

  The Bu4NI-catalyzed reaction of ketones with benzylic alcohols was achieved, leading to alfa-acyloxycarbonyl compounds in moderate to good yields. This metal-free procedure featured the employment of facilely and commercially available starting materials and TBHP as a clean oxidant with high atom economy.

  实现了Bu4NI催化的酮与苄醇的反应，以中等至良好的产率得到α-酰氧基羰基化合物。这种无金属的反应过程采用了易于获得且商业上可获得的起始原料，并使用高原子经济性的清洁氧化剂TBHP。
• Asymmetric α-oxyacylation of cyclic ketones
  作者：Deborah A. Smithen、Christopher J. Mathews、Nicholas C. O. Tomkinson

  DOI：10.1039/c2ob25293g

  日期：——

  Reaction of cyclic ketones with chiral N-alkyl-O-acyl hydroxylamines leads to the corresponding α-oxyacylated carbonyl compound in up to 89% ee. The levels of asymmetric induction were influenced by solvent polarity, acid strength and, to a lesser extent, temperature. Increasing the steric bulk around the nitrogen atom of the hydroxylamine reagent led to increased levels of asymmetric induction, which was also found to be detrimental to the yield observed for the transformation. Examination of N- and O-substituents along with substrates revealed the scope and limitations of the procedure.

  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。
• 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。