2-acetamido-8-acetylnaphthalene | 100866-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetamido-8-acetylnaphthalene
• 英文别名: N-(8-acetyl-[2]naphthyl)-acetamide；N-(8-Acetyl-[2]naphthyl)-acetamid；7-Acetamino-1-acetyl-naphthalin；1-Acetyl-7-acetylaminonaphthalin；7sAcetamino-1-acetylnaphthalin；1-Acetyl-7-acetamidonaphthalene；N-(8-acetylnaphthalen-2-yl)acetamide
• CAS: 100866-38-4
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: HJPDZOIYFTUMEE-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C
• 沸点：
  475.8±18.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetamido-8-acetylnaphthalene 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 1-Acetyl-7-cyanonaphthalin
  参考文献：
  名称：

  The Substituent Effect. XI. Solvolysis of 5-, 6-, and 7-Substituted 1-(1-Naphthylethyl) Chlorides

  摘要：

  制备了十四个5-、6-和7-取代的1-(1-萘乙基)氯化物，并在45°C下，80%（体积/体积）的乙酸水溶液中测定了其溶剂分解速率。基于方程logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+)，处理了在相应位置上的−R取代基的影响。诱导效应的位置依赖性由Cij(=ρi⁄ρi,4α)给出；C3α=1.37，C4α=1.00，C5α=0.75，C6α=0.57，C7α=0.72。Cij值似乎与Dewar的简化场函数1/rij相关。由比率ρπ+⁄ρi,4α=qr·ij+给出的π电子效应的位置依赖性与从MO指数（如Forsyth的Δqij(ArCH2+参数）的预测一致。同样的处理也应用于其他三种萘的反应性：脱氢、α-萘甲酸的pKa和萘甲基铵离子的pKa。在这些反应中，线性ρi–ρi关系成立，表明诱导传递的反应独立方案。qr·ij+值在共轭位置随反应变化，但在非共轭位置不随反应变化。结果在与相关处理的比较中进行了讨论。

  DOI：

  10.1246/bcsj.48.3356
• 作为产物：
  描述：

  1-(4,7-bis-acetylamino-[1]naphthyl)-ethanone 在 盐酸 、 sodium nitrite 、 苯 作用下， 生成 2-acetamido-8-acetylnaphthalene
  参考文献：
  名称：

  Directive Influence of the Acetylamino Group in the Friedel--Crafts Acylation of the Diacetylaminonaphthalenes

  摘要：

  DOI：

  10.1021/ja01174a016

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.
• PRODUCTS OF FRIEDEL-CRAFTS ACYLATION OF β-SUBSTITUTED NAPHTHALENES
  作者：NELSON J. LEONARD、ARCHIBALD M. HYSON

  DOI：10.1021/jo01159a022

  日期：1948.1
• SUBSTITUTED α-DIALKYLANOALKYL-1-NAPHTHALENEMETHANOLS. V. THE [ILL] OF SOME α-DIALKYLAMINOMETHYL-2-CHLORO- AND BMO-1-NAPHTHALENEMETHANOLS¹
  作者：RONALD F. BROWN、THAS L. JACOBS、S. WINSTEIN、EDWARD F. LEVYARLAND RAY MOSS、MELVLEROY OTT

  DOI：10.1021/jo01172a007

  日期：1946.3
• Some Attempts to Prepare Derivatives of Benz[f]isoquinoline and a Synthesis of Benz[h]isoquinoline¹
  作者：C. F. KOELSCH、R. M. LINDQUIST

  DOI：10.1021/jo01112a018

  日期：1956.6
• The Substituent Effect. XI. Solvolysis of 5-, 6-, and 7-Substituted 1-(1-Naphthylethyl) Chlorides
  作者：Yuho Tsuno、Masami Sawada、Takahiro Fujii、Yoshihiko Tairaka、Yasuhide Yukawa

  DOI：10.1246/bcsj.48.3356

  日期：1975.11

  Fourteen 5-, 6-, and 7-substituted 1-(1-naphthylethyl) chlorides were prepared and the solvolysis rates were determined in 80% (v/v) aqueous acetone at 45 °C. The effects of −R substituents at respective positions were treated on the basis of the equation, logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+). The position dependency of the inductive effect was given by Cij(=ρi⁄ρi,4α); C3α=1.37, C4α=1.00, C5α=0.75, C6α=0.57, and C7α=0.72. The Cij values appear to be correlated with Dewar’s simplified field function 1/rij. The position dependency of Pi-electronic effect given by the ratio ρπ+⁄ρi,4α=qr·ij+ was consistent with the prediction from the MO indices, such as Forsyth’s Δqij(ArCH2+ parameters. The same treatment was applied also to three other naphthalene reactivities, detritiation, pKa of α-naphthoic acids and pKa of naphthylammonium ions. The linear ρi–ρi relation holds among these reactions, suggesting a reaction-independent scheme of the inductive transmission. The qr·ij+ values vary at conjugate positions with reaction but not at non-conjugate positions irrespective of reactions. The results are discussed in comparison with those of relevant treatments.

  制备了十四个5-、6-和7-取代的1-(1-萘乙基)氯化物，并在45°C下，80%（体积/体积）的乙酸水溶液中测定了其溶剂分解速率。基于方程logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+)，处理了在相应位置上的−R取代基的影响。诱导效应的位置依赖性由Cij(=ρi⁄ρi,4α)给出；C3α=1.37，C4α=1.00，C5α=0.75，C6α=0.57，C7α=0.72。Cij值似乎与Dewar的简化场函数1/rij相关。由比率ρπ+⁄ρi,4α=qr·ij+给出的π电子效应的位置依赖性与从MO指数（如Forsyth的Δqij(ArCH2+参数）的预测一致。同样的处理也应用于其他三种萘的反应性：脱氢、α-萘甲酸的pKa和萘甲基铵离子的pKa。在这些反应中，线性ρi–ρi关系成立，表明诱导传递的反应独立方案。qr·ij+值在共轭位置随反应变化，但在非共轭位置不随反应变化。结果在与相关处理的比较中进行了讨论。