1-[(1R)-1-naphthalen-1-ylethyl]azetidine-2,3-dione | 212326-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(1R)-1-naphthalen-1-ylethyl]azetidine-2,3-dione
• CAS: 212326-41-5
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: XDKGHTIMUIJJDH-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Cinnamyl bromide 、 1-[(1R)-1-naphthalen-1-ylethyl]azetidine-2,3-dione 在 indium 作用下， 生成 (S)-3-Hydroxy-1-((R)-1-naphthalen-1-yl-ethyl)-3-((S)-1-phenyl-allyl)-azetidin-2-one 、 (R)-3-Hydroxy-1-((R)-1-naphthalen-1-yl-ethyl)-3-((R)-1-phenyl-allyl)-azetidin-2-one
  参考文献：
  名称：

  Diastereo- and Enantiodifferentiation in Indium-Promoted Allylations of 2,3-Azetidinediones in Water. Definition of Long-Range Stereocontrol Elements on π-Facial Selectivity for β-Lactam Synthesis

  摘要：

  The stereo chemical course of the re actions of N-benzyl-2,3-azetidinedione with six differently functionalized allylic bromides, as promoted by indium metal in 1:1 H2O-THF, were initially examined. Three of the examples that proved to be usefully stereoselective were subsequently reevaluated in azetidinediones which now carried (S)-alpha-methylbenzyl and (R)-alpha-(1-naphthyl)ethyl residues bonded to nitrogen. These enantiomerically pure building blocks afforded products that differed in the facial sense of organometallic addition to the ketonic carbonyl. Interestingly, the diastereofacial selectivity is directly linked to the R or S configuration of the exocyclic N-amido substituent. Stereochemical assignments to many of the products were based on X-ray crystallographic measurements. In other cases, spectral correlations were used. The global results clearly show that fundamental, yet previously unappreciated, long-range nonbonded steric interactions do control the extent to which competing cyclic transition states operate.

  DOI：

  10.1021/jo980372e
• 作为产物：
  描述：

  (R)-1-(1-萘基)乙胺 在 sodium periodate 、 四氧化锇 、 叔丁基氯化镁 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 30.0h， 生成 1-[(1R)-1-naphthalen-1-ylethyl]azetidine-2,3-dione
  参考文献：
  名称：

  Diastereo- and Enantiodifferentiation in Indium-Promoted Allylations of 2,3-Azetidinediones in Water. Definition of Long-Range Stereocontrol Elements on π-Facial Selectivity for β-Lactam Synthesis

  摘要：

  The stereo chemical course of the re actions of N-benzyl-2,3-azetidinedione with six differently functionalized allylic bromides, as promoted by indium metal in 1:1 H2O-THF, were initially examined. Three of the examples that proved to be usefully stereoselective were subsequently reevaluated in azetidinediones which now carried (S)-alpha-methylbenzyl and (R)-alpha-(1-naphthyl)ethyl residues bonded to nitrogen. These enantiomerically pure building blocks afforded products that differed in the facial sense of organometallic addition to the ketonic carbonyl. Interestingly, the diastereofacial selectivity is directly linked to the R or S configuration of the exocyclic N-amido substituent. Stereochemical assignments to many of the products were based on X-ray crystallographic measurements. In other cases, spectral correlations were used. The global results clearly show that fundamental, yet previously unappreciated, long-range nonbonded steric interactions do control the extent to which competing cyclic transition states operate.

  DOI：

  10.1021/jo980372e

文献信息

• Diastereo- and Enantiodifferentiation in Indium-Promoted Allylations of 2,3-Azetidinediones in Water. Definition of Long-Range Stereocontrol Elements on π-Facial Selectivity for β-Lactam Synthesis
  作者：Leo A. Paquette、Roger R. Rothhaar、Methvin Isaac、Lillian M. Rogers、Robin D. Rogers

  DOI：10.1021/jo980372e

  日期：1998.8.1

  The stereo chemical course of the re actions of N-benzyl-2,3-azetidinedione with six differently functionalized allylic bromides, as promoted by indium metal in 1:1 H2O-THF, were initially examined. Three of the examples that proved to be usefully stereoselective were subsequently reevaluated in azetidinediones which now carried (S)-alpha-methylbenzyl and (R)-alpha-(1-naphthyl)ethyl residues bonded to nitrogen. These enantiomerically pure building blocks afforded products that differed in the facial sense of organometallic addition to the ketonic carbonyl. Interestingly, the diastereofacial selectivity is directly linked to the R or S configuration of the exocyclic N-amido substituent. Stereochemical assignments to many of the products were based on X-ray crystallographic measurements. In other cases, spectral correlations were used. The global results clearly show that fundamental, yet previously unappreciated, long-range nonbonded steric interactions do control the extent to which competing cyclic transition states operate.