(S)-3-benzoyloxytetrahydro-4H-pyran-4-one | 1352653-79-2

• 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: (S)-3-benzoyloxytetrahydro-4H-pyran-4-one
• 英文别名: (R)-4-oxotetrahydro-2H-pyran-3-yl benzoate；(S)-3-benzoyloxy tetrahydropyran-4-one；[(3S)-4-oxooxan-3-yl] benzoate
• CAS: 1352653-79-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: CRLBPICQXUWPNT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  四氢吡喃酮 、 过氧化苯甲酰 在 9-amino(9-deoxy)epicinchonidine 、 sodium carbonate 、 水杨酸 作用下， 以 甲苯 为溶剂， 反应 80.0h， 以70%的产率得到(S)-3-benzoyloxytetrahydro-4H-pyran-4-one
  参考文献：
  名称：

  Enantioselective α-Benzoyloxylation of Ketones Promoted by Primary Amine Catalyst

  摘要：

  A mixture of 9-amino-(9-deoxy) epi-dihydroquinidine and salicylic acid was able to promote the direct reaction of various cyclohexanones with dibenzoyl peroxide, thus affording the corresponding protected alpha-hydroxy carbonyl compounds in high yield and enantioselectivity. Interestingly the same catalytic salt was found to be active when 1-indanones derivatives were directly employed in the reaction with dibenzoyl peroxide furnishing chiral 1-oxo-2,3-dihydro-1H-inden-2-yl benzoates in high yields and enantioselectivity. Furthermore their treatment with NaBH4 gives easy access to the corresponding enantioenriched 1,2-diols in high yields and without any loss of stereoselectivity.

  DOI：

  10.1021/jo2024976

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。
• Direct Asymmetric α Benzoyloxylation of Cyclic Ketones
  作者：Olga Lifchits、Nicolas Demoulin、Benjamin List

  DOI：10.1002/anie.201104244

  日期：2011.10.4

  business: A readily available cinchona‐derived primary amine is an effective catalyst for the direct asymmetric α benzoyloxylation of cyclic ketones (see scheme; Bz=benzoyl). This efficient and highly enantioselective method uses inexpensive benzoyl peroxide as the oxygen source and stoichiometric amounts of the ketone, and expands the current set of methodologies to directly access valuable protected 2‐hydroxyketone

  这是胺业务：易于获得的金鸡纳衍生的伯胺是有效的环酮直接不对称α苯甲酰氧基化反应的催化剂（参见方案； Bz =苯甲酰基）。这种高效且高度对映选择性的方法使用廉价的过氧化苯甲酰作为氧源和化学计量的酮，并扩展了当前的方法集，可直接使用有价值的受保护的2-羟基酮衍生物。
• Enantioselective α-Benzoyloxylation of Ketones Promoted by Primary Amine Catalyst
  作者：Milind S. Jadhav、Paolo Righi、Enrico Marcantoni、Giorgio Bencivenni

  DOI：10.1021/jo2024976

  日期：2012.3.16

  A mixture of 9-amino-(9-deoxy) epi-dihydroquinidine and salicylic acid was able to promote the direct reaction of various cyclohexanones with dibenzoyl peroxide, thus affording the corresponding protected alpha-hydroxy carbonyl compounds in high yield and enantioselectivity. Interestingly the same catalytic salt was found to be active when 1-indanones derivatives were directly employed in the reaction with dibenzoyl peroxide furnishing chiral 1-oxo-2,3-dihydro-1H-inden-2-yl benzoates in high yields and enantioselectivity. Furthermore their treatment with NaBH4 gives easy access to the corresponding enantioenriched 1,2-diols in high yields and without any loss of stereoselectivity.