(3S)-3-phenylheptan-2-one | 54929-04-3

• 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: (3S)-3-phenylheptan-2-one
• 英文别名: (S)-3-phenylheptan-2-one；(S)-3-phenyl-heptan-2-one；(S)-3-Phenyl-heptan-2-on
• CAS: 54929-04-3
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: GOCPGZPCTSKYKW-CYBMUJFWSA-N

物化性质

• 沸点：
  250-251 °C
• 密度：
  0.9597 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(+)-2-phenylhexanoic acid 、 甲基锂 在 乙醚 作用下， 生成 (3S)-3-phenylheptan-2-one
  参考文献：
  名称：

  The Effect of Ring Formation on Optical Rotatory Power. A Comparison of the Optical Rotations of 2-Phenylcyclopentanone and of Some Acyclic α-Phenyl Ketones

  摘要：

  DOI：

  10.1021/ja01611a056

文献信息

• Application of a Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase
  作者：Panee C. Hutchison、Tom D. Heightman、David J. Procter

  DOI：10.1021/jo0354950

  日期：2004.2.1

  A pseudoephedrine resin has been successfully employed in asymmetric alkylations on solid phase. Immobilized pseudoephedrine amides are conveniently prepared by the one-step attachment of pseudoephedrine to Merrifield resin through the hydroxyl group and subsequent acylation on nitrogen. Deprotonation and alkylation of the resin-bound amides proceeds smoothly. Ketones and alcohols are cleaved from

  伪麻黄碱树脂已成功用于固相不对称烷基化反应中。固定的伪麻黄碱酰胺可通过将伪麻黄碱通过羟基一步一步连接到Merrifield树脂并随后在氮上酰化来方便地制备。与树脂结合的酰胺的去质子化和烷基化反应顺利进行。酮和醇以高对映异构体过量和中等至良好的总收率从树脂上裂解下来。进行了手性酮和醇的小型文库的平行，不对称固相合成，以说明该方法的实用性。最后，伪麻黄碱树脂可以方便地回收和利用，而产物的收率或对映体过量没有明显损失。
• Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2009.03.018

  日期：2009.6

  The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic alpha-alkyl benzylketones with longer alkyl chains as well as with two substituted alpha-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
• Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase
  作者：Panee C. Hutchison、Tom D. Heightman、David J. Procter

  DOI：10.1021/ol0268788

  日期：2002.12.1

  Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.