2-(Benzoyloxy)cycloheptanone | 53429-51-9

• 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-(Benzoyloxy)cycloheptanone
• 英文别名: 2-benzoyloxy cycloheptanone；2-oxocycloheptyl benzoate；α-Benzoyloxycycloheptanon；2-Benzoyloxycycloheptanon；(2-Oxocycloheptyl) benzoate
• CAS: 53429-51-9
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: APFABFFIGWWJSK-UHFFFAOYSA-N

物化性质

• 熔点：
  57-57.5 °C
• 沸点：
  360.4±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  环庚烯-1-氧基(三甲基)硅烷 在 碘 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(Benzoyloxy)cycloheptanone
  参考文献：
  名称：

  Reaction of enol silyl ethers with silver carboxylate-iodine. Synthesis of .alpha.-acyloxy carbonyl compounds

  摘要：

  DOI：

  10.1021/jo00326a023

文献信息

• 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。
• One-pot synthesis of α-acyloxycarbonyl compounds via oxidative decarboxylation coupling reaction of α-oxo carboxylic acids with carbonyl compounds
  作者：Li-Ming Chang、Gao-Qing Yuan

  DOI：10.1016/j.tet.2016.09.031

  日期：2016.11

  With tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, a simple metal-free protocol has been developed for the synthesis of α-acyloxycarbonyl compounds from carbonyl compounds and α-oxo carboxylic acids via decarboxylative coupling reaction. The target products could be obtained in moderate to high yields.

  以碘化四丁基铵（TBAI）为催化剂，叔丁基过氧化氢（TBHP）为氧化剂，已开发出一种简单的无金属方案，用于通过脱羧偶联从羰基化合物和α-氧代羧酸合成α-酰氧羰基化合物反应。可以以中等至高收率获得目标产物。
• A PRACTICAL PROCEDURE FOR CARBONYL a-OXIDATION: SYNTHESIS OF (2-BENZOYLOXY)-1,4-CYCLOHEXANEDIONE MONO-ETHYLENE KETAL
  作者：Jones, Teyrnon C.、Tomkinson, Nicholas C. O.、Patil, Kalyani、Wipf, Peter

  DOI：10.15227/orgsyn.084.0233

  日期：——
• 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.
• RUBOTTOM G. M.; MOTT R. C.; JUVE H. D., J. ORG. CHEM., 1981, 46, NO 13, 2717-2721
  作者：RUBOTTOM G. M.、 MOTT R. C.、 JUVE H. D.

  DOI：——

  日期：——