2-(benzoyloxy)-4-methylcyclohexanone | 66049-59-0

• 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)-4-methylcyclohexanone
• 英文别名: 5-Methyl-2-oxocyclohexyl-benzoat；(5-Methyl-2-oxocyclohexyl) benzoate；(5-methyl-2-oxocyclohexyl) benzoate
• CAS: 66049-59-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: IKRGEJRUKUEADK-UHFFFAOYSA-N

物化性质

• 沸点：
  350.4±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：

  N-(tert-butyloxycarbonyl)-N-methyl-O-benzoyl-hydroxylamine 在 盐酸 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 2-(benzoyloxy)-4-methylcyclohexanone
  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

• Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides
  作者：Michelle A. Kroc、Aditi Patil、Anthony Carlos、Josiah Ballantine、Stephanie Aguilar、Dong-Liang Mo、Heng-Yen Wang、Daniel S. Mueller、Donald J. Wink、Laura L. Anderson

  DOI：10.1016/j.tet.2017.01.061

  日期：2017.7

  synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations

  合成α-氧化羰基化合物和邻苯二酚的常用方法是用亲电子氧源处理羰基化合物或苯酚。作为这些重要结构的替代方法，已经研究了N-烯氧基邻苯二甲酰亚胺，N-烯氧基异吲哚满酮和N-芳氧基邻苯二甲酰亚胺的形式[3,3]重排。当与初始Chan-Lam偶联结合使用时，这些转化有助于烯基硼酸的双氧合以合成α-加氧的酮和芳基硼酸的双氧合以合成儿茶酚。N-烯氧基异吲哚啉酮的重排也已显示为非对映选择性的。