(R)-4-phenyloctan-3-one | 1173092-43-7

• 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: (R)-4-phenyloctan-3-one
• 英文别名: (4R)-4-phenyloctan-3-one
• CAS: 1173092-43-7
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: WXNIUXZZYBHUKQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4,4,5,5-tetramethyl-2-(1-phenylpentyl)-1,3,2-dioxaborolane 在 乙二醇二甲醚溴化镍 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 (R,R)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.08h， 生成 (R)-4-phenyloctan-3-one
  参考文献：
  名称：

  光氧化还原/镍催化对映异构酰基与有机三氟硼酸酯交叉偶联合成手性 α-芳基酮

  摘要：

  开发了光氧化还原/镍催化的对映会聚酰基交叉偶联，用于在温和中性条件下合成烯醇化手性 α-芳基酮。实现了中等到高产率和良好的对映选择性。

  DOI：

  10.1021/acs.orglett.3c04004

文献信息

• 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.
• Synthesis of Chiral α-Aryl Ketones by Photoredox/Nickel-Catalyzed Enantioconvergent Acyl Cross-Coupling with Organotrifluoroborate
  作者：Weichen Wang、Chaoren Shen、Linli Zhang、Kaiwu Dong

  DOI：10.1021/acs.orglett.3c04004

  日期：2024.2.2

  Photoredox/nickel-catalyzed enantioconvergent acyl cross-coupling of carboxylic derivatives with racemic secondary organotrifluoroborate was developed for the synthesis of an enolizable chiral α-aryl ketone under mild neutral conditions. Moderate to high yields and good enantioselectivities were achieved.

  开发了光氧化还原/镍催化的对映会聚酰基交叉偶联，用于在温和中性条件下合成烯醇化手性 α-芳基酮。实现了中等到高产率和良好的对映选择性。