6-acetyl-2-naphthyl acetate | 63256-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-acetyl-2-naphthyl acetate
• 英文别名: 6-Acetylnaphthalen-2-yl acetate；(6-acetylnaphthalen-2-yl) acetate
• CAS: 63256-69-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: NFLXDPGRGJAZPK-UHFFFAOYSA-N

物化性质

• 沸点：
  380.5±15.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  6-acetyl-2-naphthyl acetate 在 氧气 、 manganese (II) acetate tetrahydrate 、 cobalt(II) diacetate tetrahydrate 、 溶剂黄146 作用下， 反应 15.0h， 以66%的产率得到6-乙酰基-2-萘甲酸
  参考文献：
  名称：

  Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst

  摘要：

  A new strategy to 6-hydroxy-2-naphthoic acid (HNPA) and 4-hydroxybenzoic acid from 2,6-diisopropylnaphthalene and p-cymene, respectively, was developed using the NHPI-catalyzed aerobic oxidation as a principal reaction. 2,6-Diisopropylnaphthalene was oxidized by the oxidation with O-2 (1 atm) by NHPI (10 mol %) combined with Co(OAc)(2) (0.5 mol %) to give 6-acetyl-2 -isopropylnaphthalene, which then was converted to 6-isopropyl-2-naphthoic acid Under O-2 (1 atm) in the presence of Co(OAc)(2) (0.5 mol %) and Mn(OAc)(2) (0.5 mol %), Esterification of the resulting acid followed by the aerobic oxidation produced methyl 6-hydroxy-2-naphthoate whose hydrolysis led to the desired HNPA. An alternative route involves the oxidation of 6-acetyl-2-isopropylnaphthalene to 6-acetyl-2-naphthol on which subsequent oxidation and deacetylation gave HNPA. This method was Successfully extended to the synthesis of 4-hydroxybenzoic acid from p-cymene. (C) 2009 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.013
• 作为产物：
  描述：

  6-乙酰基-2-萘酚 生成 6-acetyl-2-naphthyl acetate
  参考文献：
  名称：

  DAVENPORT, KENNETH G.;HILTON, CHARLES B.

  摘要：

  DOI：

文献信息

• A linear Br�nsted-type behavior in the aminolysis of substituted naphthyl acetates
  作者：D. Rajarathnam、P. Ananthakrishna Nadar

  DOI：10.1002/1097-4601(200103)33:3<157::aid-kin1009>3.0.co;2-y

  日期：2001.3

  The reactions of 4-acetyl-1-naphthyl acetate (I) and 6-acetyl-2-naphthyl acetate (2) with a series of amines of varying pK(a),viz, morpholine, ammonia, ethanolamine, glycine n-butylamine, piperidine. hydrazine, imidazole, and hydroxylamine, are subjected to a kinetic investigation in aqueous medium. 30 degreesC, ionic strength 0.1 M (KCl). Pseudo-first-order rate coefficients (k(obs)) are found under amine excess. The plots of (k(obs) - k(H)) against free amine concentration are linear at constant pH. The macroscopic nucleophilic substitution rate coefficients (k(N)) are obtained as the slopes of these plots and found to be pH-independent for all the amines employed. The Bronsted-type plots obtained (log k(N) against amine pK(a)) for the aminolysis of both esters 1 and 2 are linear with slope values of beta = 0.74 and beta = 0.94, respectively. From these values, the kinetic law and the analysis of products. it is deduced that for both esters aminolysis proceed through a zwitterionic tetrahedral addition intermediate (T+/-) whereby its dissociation into products is rate-limiting (k(2) step). Comparison of k(N) values among them shows that both esters follow an identical mechanistic pathway with 1 having higher reactivity than 2, the reasons for which are discussed. (C) 2001 John Wiley & Sons Inc.
• Biaryl Construction via Ni-Catalyzed C−O Activation of Phenolic Carboxylates
  作者：Bing-Tao Guan、Yang Wang、Bi-Jie Li、Da-Gang Yu、Zhang-Jie Shi

  DOI：10.1021/ja8056503

  日期：2008.11.5

  Biaryl scaffolds were constructed via Ni-catalyzed aryl C-O activation by avoiding cleavage of the more reactive acyl C-O bond aryl carboxylates. Now aryl esters, in general, can be successfully employed in cross-coupling reactions for the first time. The substrate scope and synthetic utility of the chemistry were demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. Water was observed to play an important role in facilitating this transformation.
• Ananthakrishna Nadar; Rajarathinam, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1998, vol. 37, # 4, p. 342 - 345
  作者：Ananthakrishna Nadar、Rajarathinam

  DOI：——

  日期：——
• ROHRSCHEID, FREIMUND
  作者：ROHRSCHEID, FREIMUND

  DOI：——

  日期：——
• ——
  作者：DAVENPORT K. G.、 LINSTID H. C., III

  DOI：——

  日期：——