4-acetyl-1-naphthyl acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-acetyl-1-naphthyl acetate
• 英文别名: (4-Acetylnaphthalen-1-yl) acetate；(4-acetylnaphthalen-1-yl) acetate
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: UVSJDZFZAUHVGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：

  4-acetyl-1-naphthyl acetate 在 羟胺 作用下， 以 水 为溶剂， 生成 乙酰氧肟酸 、 1-(4-羟基萘-1-基)乙酮
  参考文献：
  名称：

  A linear Br�nsted-type behavior in the aminolysis of substituted naphthyl acetates

  摘要：

  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.

  DOI：

  10.1002/1097-4601(200103)33:3<157::aid-kin1009>3.0.co;2-y
• 作为产物：
  描述：

  乙酸酐 、 tert-butyldimethyl(naphthalen-1-yloxy)silane 在 perchloric acid immobilized on silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以78%的产率得到4-acetyl-1-naphthyl acetate
  参考文献：
  名称：

  An atom-efficient and powerful method for direct esterification of silyl ethers catalyzed by HClO4–SiO2

  摘要：

  An efficient and convenient procedure for direct esterification of alkyl and aryl silyl ethers with Ac2O and a catalyst system of perchloric acid immobilized on a silica gel (HClO4 SiO2) has been developed. The silyl protecting groups are directly replaced by acetyls and the protecting groups themselves are transformed into acetates as the sole byproducts, which can be readily recovered and converted back to silylchlorides, the original protecting agents, thus minimizing wastes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.028

文献信息

• DE2061864
  申请人：——

  公开号：——

  公开（公告）日：——
• CH566963
  申请人：——

  公开号：——

  公开（公告）日：——
• Ananthakrishna Nadar; Rajarathinam, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1997, vol. 36, # 9, p. 749 - 753
  作者：Ananthakrishna Nadar、Rajarathinam

  DOI：——

  日期：——
• 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.
• An atom-efficient and powerful method for direct esterification of silyl ethers catalyzed by HClO4–SiO2
  作者：Ti-Jian Du、Qin-Pei Wu、Hai-Xia Liu、Xi Chen、Yi-Nan Shu、Xiao-Dong Xi、Qing-Shan Zhang、Yun-Zheng Li

  DOI：10.1016/j.tet.2010.12.028

  日期：2011.2

  An efficient and convenient procedure for direct esterification of alkyl and aryl silyl ethers with Ac2O and a catalyst system of perchloric acid immobilized on a silica gel (HClO4 SiO2) has been developed. The silyl protecting groups are directly replaced by acetyls and the protecting groups themselves are transformed into acetates as the sole byproducts, which can be readily recovered and converted back to silylchlorides, the original protecting agents, thus minimizing wastes. (C) 2010 Elsevier Ltd. All rights reserved.