6-benzoyltetrahydro-2H-pyran-2-one | 184171-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-benzoyltetrahydro-2H-pyran-2-one
• 英文别名: 6-Benzoyloxan-2-one
• CAS: 184171-69-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: OZYKMQHVGUVFFM-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C
• 沸点：
  391.1±35.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-benzoyltetrahydro-2H-pyran-2-one 生成 5-羟基-5-苯甲酰戊酸
  参考文献：
  名称：

  Surface photoreactions of 2-benzoylcyclopentanones: Silica gel surface as a possible field bringing out the latent reactivity of dispersed molecules

  摘要：

  Irradiation of 2-benzoyl- and 2-(p-methylbenzoyl)cyclopentanone (la and Ib), which have the lowest n,pi* excited states and showed no photoreactivities in inert solvents, neat or in the solid state, gave two types of products on a silica gel surface; one arose from the cleavage of the C-C bond a to the benzoyl group and the other arose from the cyclopentanone C-1-C-2 bond cleavage. Analysis of Langmuir adsorption isotherm of la by a non-linear least-squares method revealed that 7.9 x 10(-4) mot of 1a was spread as a monomolecular layer over 1 g of silica gel, The photoreactivity of 1a on the surface was very sensitive to the coverage; the efficiency of disappearance of la decreased monotonically from 100% at low coverages to zero at nearly 100% coverage. Close packing of molecules of 1 on the surface diminished the photoreactivity. A silica gel surface provided a possible dispersion field for bringing out the latent photoreactivity of 1.

  DOI：

  10.1002/(sici)1099-1395(199610)9:10<677::aid-poc838>3.0.co;2-n
• 作为产物：
  描述：

  5-苯(甲)酰戊酸 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 168.0h， 以62%的产率得到6-benzoyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  DDQ促进了天然刚性多环酸或柔性烷基酸的脱氢，通过自由基离子机理生成内酯。

  摘要：

  描述了一种新颖且容易的DDQ介导的从天然刚性多环酸或柔性烷基酸脱氢生成内酯的方法。内酯的形成是通过自由基离子机理进行的，该机理已通过DPPH介导的化学鉴定，ESR光谱和烯醇中间体捕集得以确立。

  DOI：

  10.1039/c1cc11633a

文献信息

• In Situ Generated (Hypo)Iodite Catalysts for the Direct α-Oxyacylation of Carbonyl Compounds with Carboxylic Acids
  作者：Muhammet Uyanik、Daisuke Suzuki、Takeshi Yasui、Kazuaki Ishihara

  DOI：10.1002/anie.201101522

  日期：2011.5.27

  It′s the iodine: The intra‐ and intermolecular title reaction is catalyzed by an in situ generated ammonium (hypo)iodite species. Either H2O2 or tert‐butyl hydroperoxide (TBHP) can be used as an environmentally benign oxidant and a wide range of substrates react to give the corresponding α‐acyloxycarbonyl compounds in good to excellent yields.

  它是碘：分子内和分子间标题反应是由原位生成的亚碘铵（次同）催化的。H 2 O 2或叔丁基氢过氧化物（TBHP）都可以用作环境友好的氧化剂，并且多种底物反应生成相应的α-酰氧基羰基化合物，收率良好至优异。
• Photoredox-catalyzed regio- &amp; stereoselective C(sp²)–H cyanoalkylation of enamides with cycloketone oximes <i>via</i> selective C–C bond cleavage/radical addition cascade
  作者：Ting Guan、Jing-Yu Guo、Qing-Hong Zhang、Xin-Wen Xu、Xiao-Yu Yu、Yu Zhang、Kai Zhao

  DOI：10.1039/d2gc01978g

  日期：——

  A photoredox-catalyzed regio- and stereoselective Heck-type cyanoalkylation of synthetically prominent enamides with cycloketone oximes via selective β-C–C bond scission/selective radical addition cascade is developed, enabling the incorporation of synthetically versatile and pharmaceutically appealing distal cyanoalkyl moieties into enamide scaffolds under mild conditions. The synthetic importance

  开发了一种光氧化还原催化的区域选择性和立体选择性 Heck 型氰烷基化合成突出的烯酰胺与环酮肟通过选择性 β-C-C 键断裂/选择性自由基加成级联反应，从而能够将合成通用和药学上有吸引力的远端氰烷基部分结合到烯酰胺中温和条件下的支架。广泛的底物范围、令人满意的官能团相容性、优异的区域和立体选择性以及 β-氰基烷基化烯酰胺的多种合成应用突出了该方法的合成重要性。
• Calcium iodide catalyzed photooxidative oxylactonization of oxocarboxylic acids using molecular oxygen as terminal oxidant
  作者：Norihiro Tada、Takafumi Ishigami、Lei Cui、Kazunori Ban、Tsuyoshi Miura、Akichika Itoh

  DOI：10.1016/j.tetlet.2012.11.014

  日期：2013.1

  We developed aerobic photooxidative oxylactonization of oxocarboxylic acids catalyzed by calcium iodide using molecular oxygen as the terminal oxidant under photo irradiation. (C) 2012 Elsevier Ltd. All rights reserved.
• Hypervalent iodine-catalyzed oxylactonization of ketocarboxylic acids to ketolactones
  作者：Muhammet Uyanik、Takeshi Yasui、Kazuaki Ishihara

  DOI：10.1016/j.bmcl.2009.03.148

  日期：2009.7

  The hypervalent iodine-catalyzed oxylactonization of ketocarboxylic acids to ketolactones was achieved in the presence of iodobenzene (10 mol %), p-toluenesulfonic acid monohydrate (20 mol %) and meta-chloroperbenzoic acid as a stoichiometric co-oxidant. (C) 2009 Elsevier Ltd. All rights reserved.