N-(4-氨基苄基)乙酰胺盐酸盐 | 24095-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-氨基苄基)乙酰胺盐酸盐
• 英文名称: N-(4-aminobenzyl)acetamide hydrochloride
• 英文别名: Acetamide,N-[(4-aminophenyl)methyl]-, hydrochloride (1:1)；N-[(4-aminophenyl)methyl]acetamide;hydrochloride
• CAS: 24095-59-8
• 化学式: C₉H₁₂N₂O*ClH
• 分子量: 200.668
• InChiKey: XYKRLYLDAOQRPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酸酐 、 4-aminobenzylamine dihydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 以85%的产率得到N-(4-氨基苄基)乙酰胺盐酸盐
  参考文献：
  名称：

  pH optimization of nucleophilic reactions in water

  摘要：

  We present a way of prescribing the pH for a reaction so as to obtain either (a) maximum yield in competition with hydrolysis or (b) selective reaction at either of two sites in such nucleophile-electrophile reactions as C-alkylation of acidic ketones and the acylation and sulfonylation of amines. First, we derive the following general equation for pH(max), the pH giving the highest yield of the product (P) of the reaction of a nucleophile (Nu) with a hydrolyzable electrophile (E) in water: pH(max) = 1/2[log (k(w)/k(OH)) + pK(w) + pK(a)] (k(w) and k(OH) refer to the water- and hydroxide-promoted hydrolyses of E, K(w) is the autoprotolysis constant of water, and K(a) is the acid dissociation constant of NuH+, the conjugate acid of Nu). pH(max) thus depends on a property of E (namely, k(w)/k(OH)) and a property of Nu (the pK(a) of NuH+), but not on the rate constant for the reaction of E with Nu or the concentration of Nu. We then deduce analogous approximate equations for maximum selectivity for reaction at either of two nucleophilic sites, specifically, equations giving pH(xmax) and pH(ymax), the pH values for the maximum yields of the respective products (P(x) and P(y)) of the reactions of E with the two nucleophiles. We find that (a) pH-yield profiles calculated from the equations concur with observed yields for reactions under pseudo-first-order conditions and (b) preparative experiments at the estimated pH values give good to excellent yields of clean products and high selectivity in both the C-alkylation and Schotten-Baumann reactions.

  DOI：

  10.1021/ja00034a040

文献信息

• US4672067A
  申请人：——

  公开号：US4672067A

  公开（公告）日：1987-06-09
• pH optimization of nucleophilic reactions in water
  作者：J. F. King、R. Rathore、J. Y. L. Lam、Z. R. Guo、D. F. Klassen

  DOI：10.1021/ja00034a040

  日期：1992.4

  We present a way of prescribing the pH for a reaction so as to obtain either (a) maximum yield in competition with hydrolysis or (b) selective reaction at either of two sites in such nucleophile-electrophile reactions as C-alkylation of acidic ketones and the acylation and sulfonylation of amines. First, we derive the following general equation for pH(max), the pH giving the highest yield of the product (P) of the reaction of a nucleophile (Nu) with a hydrolyzable electrophile (E) in water: pH(max) = 1/2[log (k(w)/k(OH)) + pK(w) + pK(a)] (k(w) and k(OH) refer to the water- and hydroxide-promoted hydrolyses of E, K(w) is the autoprotolysis constant of water, and K(a) is the acid dissociation constant of NuH+, the conjugate acid of Nu). pH(max) thus depends on a property of E (namely, k(w)/k(OH)) and a property of Nu (the pK(a) of NuH+), but not on the rate constant for the reaction of E with Nu or the concentration of Nu. We then deduce analogous approximate equations for maximum selectivity for reaction at either of two nucleophilic sites, specifically, equations giving pH(xmax) and pH(ymax), the pH values for the maximum yields of the respective products (P(x) and P(y)) of the reactions of E with the two nucleophiles. We find that (a) pH-yield profiles calculated from the equations concur with observed yields for reactions under pseudo-first-order conditions and (b) preparative experiments at the estimated pH values give good to excellent yields of clean products and high selectivity in both the C-alkylation and Schotten-Baumann reactions.