6-methoxy-4-(2'-propenyl)naphthalene-2-carboxylic acid | 139633-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxy-4-(2'-propenyl)naphthalene-2-carboxylic acid
• 英文别名: 6-Methoxy-4-prop-2-enylnaphthalene-2-carboxylic acid
• CAS: 139633-67-3
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: PVCOBFVTPXRPIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-dihydro-7-methoxy-N-(1',1'-dimethylethyl)-1-(2'-propenyl)naphthalene-3-sulfonamide 、 氯甲酸甲酯 、 碘甲烷 生成 6-methoxy-4-(2'-propenyl)naphthalene-2-carboxylic acid
  参考文献：
  名称：

  Metal-ammonia reduction and reductive alkylation of N-alkylnaphthalenesulfonamides. A new route to substituted naphthalenes

  摘要：

  Conditions have been found for 1,4-reduction of aromatic sulfonamides (conveniently monitored by electrical conductivity), using metals in THF/liquid ammonia on the pre-formed N-lithium salts (BuLi), without concomitant C-S reductive cleavage. The resulting 1,4-dihydro compounds could be alkylated, either in situ (in the case of simple unfunctionalized halides only) or, following isolation, after further N-alkylation and then forming the monoanion, or after forming the dianion of the N-monoalkylated dihydrosulfonamide, generally using as base n-butyllithium (a simple titration procedure). In the former case functionalized electrophiles (bromo esters, chloroformates) could be utilized. The ratio of alpha- to gamma-alkylation was dependent on the method of alkylation, the reaction medium, the nature of the N-alkyl group(s), and whether a monoanion or a dianion served as substrate. Gamma-Alkylation products could in some cases be further alpha-substituted. The alpha-substituted products aromatized, with loss of SO2 and amine, by heating, whereas gamma-substitution products required hydrolysis by aqueous alkali; this greatly facilitated separation where mixtures were formed. Thus, this dihydrosulfonamide route constitutes a novel and nucleophilic route to 1-substituted, 2-substituted, and, notably, 1,3-disubstituted naphthalenes.

  DOI：

  10.1021/jo00035a018