methyl 4-oxo-7-phenylheptanoate | 160723-52-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4-oxo-7-phenylheptanoate
• 英文别名: Methyl I(3)-oxobenzeneheptanoate
• CAS: 160723-52-4
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: RCSUVOMLQYKPDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  methyl 4-oxo-7-phenylheptanoate 在 palladium bis(2,2,6,6-tetramethyl-3,5-heptanedione) 、 potassium tert-butylate 、 1-azido-3,3-dimethyl-3-(1H)-1,2-benziodoxole 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 5-(azidomethyl)-5-(3-phenylpropyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  使用高价碘试剂从烯烃对（1,1）和（1,2）-叠氮内酯的不同访问

  摘要：

  通过将羧酸叠氮化和环化到烯烃上，已开发了一种通用的叠氮内酯合成方法。基于光氧化还原或钯催化，可以选择性地合成（1,1）和（1,2）叠氮基内酯。选择催化剂和用作叠氮化物源的苯并齐多醇试剂对于引发自由基或路易斯酸介导的过程具有不同的结果至关重要。这些转化是在温和的条件下使用低催化剂负载量进行的，并获得了大范围的叠氮基内酯。

  DOI：

  10.1002/chem.201702599
• 作为产物：
  描述：

  4-硝基丁酸甲酯 在 aluminum oxide 、 sodium hypophosphite 、 buffer acetate 、 镍 作用下， 以 乙醇 为溶剂， 反应 38.0h， 生成 methyl 4-oxo-7-phenylheptanoate
  参考文献：
  名称：

  Ballini, Roberto; Bosica, Giovanna, Journal of Chemical Research, Miniprint, 1993, # 11, p. 2901 - 2912

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed Three-Component Coupling via Hydrative Conjugate Addition of Alkynes to Alkenes: One-Pot Synthesis of 1,4-Dicarbonyl Compounds
  作者：Yiyun Chen、Sung Hwan Park、Chung Whan Lee、Chulbom Lee

  DOI：10.1002/asia.201100266

  日期：2011.8.1

  A catalytic three‐way rendezvous: Terminal alkynes undergo metal vinylidene formation, anti‐Markovnikov hydration to give a metal acyl complex, and conjugate addition to produce synthetically useful 1,4‐dicarbonyl compounds under ruthenium catalysis. This one‐pot three‐component coupling reaction is a useful platform for further exploration in alkyne functionalization.

  催化三重集合点：末端炔烃经历金属亚乙烯基的形成，反马氏水合形成金属酰基配合物，并在钌催化下加成共轭物以生产合成上有用的1,4-二羰基化合物。这一单锅三组分偶联反应为进一步探索炔烃功能化提供了有用的平台。
• Generation of Acyl Radicals from 1-Oxidoalkylidenechromium(0) Complexes by Treatment with Bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II) and Their Reactions with Olefins
  作者：Hidehiro Sakurai、Koichi Narasaka

  DOI：10.1246/cl.1994.2017

  日期：1994.11

  Tetramethylammonium pentacarbonyl(1-oxidoalkylidene)chromium(0) complexes are oxidized with bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II) to generate acyl radicals which react with electron-deficient olefins, giving intermolecular addition products.

  四甲基铵五羰基（1-氧化亚烷基）铬（0）配合物与双（2,2,6,6-四甲基-3,5-庚二酮）铜（II）氧化生成酰基自由基，与缺电子烯烃反应，得到分子间加成产物。
• Process-scale preparation of enantiomerically pure γ-lactones by asymmetric hydrogenation of γ-ketoesters and comparative tests of the sensory properties of some antipodes
  作者：Tiziana Benincori、Simona Rizzo、Tullio Pilati、Alessandro Ponti、Mara Sada、Ella Pagliarini、Simona Ratti、Celentano Giuseppe、Lorenzo de Ferra、Franco Sannicolò

  DOI：10.1016/j.tetasy.2004.06.024

  日期：2004.7

  A reliable methodology, applicable on a process-scale level, for producing enantiomerically pure chiral gamma-lactones by enantioselective hydrogenation of gamma-ketoesters, followed by cyclisation of the resulting gamma-hydroxyesters, has been developed. The multi-step procedure was transformed into a one-pot reaction. A very efficient chiral Ru-complex, based on the bilieteroaromatic diphosphine ligand tetraMe-BITIOP, was developed as a catalyst, capable of coupling fast kinetics with high stereoselection levels. Its structure was fully elucidated through P-31 NMR, EPR and X-ray single-crystal analyses. The optimal experimental conditions are as follows: hydrogen pressure = 30 psi, S/C ratio = 2000, 30% in weight substrate concentration. Yields are quantitative and enantiomeric excesses in the range 98-99.9%. Sensorial tests on the antipodes of two gamma-lactones demonstrated the very different properties of the enantiomers. (C) 2004 Published by Elsevier Ltd.