8-myristoyl-2-naphthyl acetate | 959296-10-7

• 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: 8-myristoyl-2-naphthyl acetate
• 英文别名: 7-Acetoxy-1-myristoyl-naphthalene；(8-tetradecanoylnaphthalen-2-yl) acetate
• CAS: 959296-10-7
• 化学式: C₂₆H₃₆O₃
• 分子量: 396.57
• InChiKey: JIFGKALSUWXWKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  8-myristoyl-2-naphthyl acetate 生成 8-myristoyl-2-naphthol
  参考文献：
  名称：

  Investigation of the Photo-Fries Rearrangements of Two 2-Naphthyl Alkanoates by Experiment and Theory. Comparison with the Acid-Catalyzed Reactions

  摘要：

  A detailed investigation of the photochemistry of a-naphthyl acetate (1a) and 2-naphthyl myristate (1b) has been conducted under a variety of conditions. Factors related to the reactions such as temperature and solvent type have been explored. The results, most easily interpreted by photo-Fries type processes, are contrasted with those from the Lewis-acid catalyzed (dark) Fries reactions of 1a. They are also compared to the predictions of semiempirical and ab initio calculations using 2-naphthyl propanoate (1c) and species derived from it as models. Unsuccessful triplet sensitization experiments with benzophenone and calculations point to the excited singlet states of 1 as the immediate precursor to the acyl/2-naphthoxy radical pairs that recombine to form keto intermediates 2, reform 1, or diffuse apart and eventually yield 2-naphthol (4); enolization of 2 results in the isolated rearrangement products, n-acyl-2-naphthols (n-3). Static and dynamic fluorescence studies provide some insights into the nature of the lysis process. Irradiation of a mixture of appropriately labeled derivatives of 1 led to none of the expected ''cross-over'' products, indicating that the intermediates 2 arise from recombination of radical pairs from the same parent molecule. Irradiation of 1b in ethanol and 1-octanol provides no evidence for the intermediacy of dodecylketene and supports out-of-cage mechanisms as the exclusive source of 4. There are indications of subtle solvent effects and a conformational dependence on the distribution of photoproducts.

  DOI：

  10.1021/jo952108g
• 作为产物：
  描述：

  N-乙醯萘胺 在 三氯化铝 、 硫酸 、 sodium nitrite 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 5.33h， 生成 8-myristoyl-2-naphthyl acetate
  参考文献：
  名称：

  Investigation of the Photo-Fries Rearrangements of Two 2-Naphthyl Alkanoates by Experiment and Theory. Comparison with the Acid-Catalyzed Reactions

  摘要：

  A detailed investigation of the photochemistry of a-naphthyl acetate (1a) and 2-naphthyl myristate (1b) has been conducted under a variety of conditions. Factors related to the reactions such as temperature and solvent type have been explored. The results, most easily interpreted by photo-Fries type processes, are contrasted with those from the Lewis-acid catalyzed (dark) Fries reactions of 1a. They are also compared to the predictions of semiempirical and ab initio calculations using 2-naphthyl propanoate (1c) and species derived from it as models. Unsuccessful triplet sensitization experiments with benzophenone and calculations point to the excited singlet states of 1 as the immediate precursor to the acyl/2-naphthoxy radical pairs that recombine to form keto intermediates 2, reform 1, or diffuse apart and eventually yield 2-naphthol (4); enolization of 2 results in the isolated rearrangement products, n-acyl-2-naphthols (n-3). Static and dynamic fluorescence studies provide some insights into the nature of the lysis process. Irradiation of a mixture of appropriately labeled derivatives of 1 led to none of the expected ''cross-over'' products, indicating that the intermediates 2 arise from recombination of radical pairs from the same parent molecule. Irradiation of 1b in ethanol and 1-octanol provides no evidence for the intermediacy of dodecylketene and supports out-of-cage mechanisms as the exclusive source of 4. There are indications of subtle solvent effects and a conformational dependence on the distribution of photoproducts.

  DOI：

  10.1021/jo952108g

文献信息

• Investigation of the Photo-Fries Rearrangements of Two 2-Naphthyl Alkanoates by Experiment and Theory. Comparison with the Acid-Catalyzed Reactions
  作者：Changxing Cui、Xiaochun Wang、Richard G. Weiss

  DOI：10.1021/jo952108g

  日期：1996.1.1

  A detailed investigation of the photochemistry of a-naphthyl acetate (1a) and 2-naphthyl myristate (1b) has been conducted under a variety of conditions. Factors related to the reactions such as temperature and solvent type have been explored. The results, most easily interpreted by photo-Fries type processes, are contrasted with those from the Lewis-acid catalyzed (dark) Fries reactions of 1a. They are also compared to the predictions of semiempirical and ab initio calculations using 2-naphthyl propanoate (1c) and species derived from it as models. Unsuccessful triplet sensitization experiments with benzophenone and calculations point to the excited singlet states of 1 as the immediate precursor to the acyl/2-naphthoxy radical pairs that recombine to form keto intermediates 2, reform 1, or diffuse apart and eventually yield 2-naphthol (4); enolization of 2 results in the isolated rearrangement products, n-acyl-2-naphthols (n-3). Static and dynamic fluorescence studies provide some insights into the nature of the lysis process. Irradiation of a mixture of appropriately labeled derivatives of 1 led to none of the expected ''cross-over'' products, indicating that the intermediates 2 arise from recombination of radical pairs from the same parent molecule. Irradiation of 1b in ethanol and 1-octanol provides no evidence for the intermediacy of dodecylketene and supports out-of-cage mechanisms as the exclusive source of 4. There are indications of subtle solvent effects and a conformational dependence on the distribution of photoproducts.