1,4-dihydro-6-methoxy-N-methylnaphthalene-2-sulfonamide | 121429-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-dihydro-6-methoxy-N-methylnaphthalene-2-sulfonamide
• 英文别名: 6-methoxy-N-methyl-1,4-dihydronaphthalene-2-sulfonamide
• CAS: 121429-67-2
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: OXVQZLIYOQLBGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-methoxy-N-methylanphthalene-2-sulfonamide 在 正丁基锂 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 1,2-dihydro-6-methoxy-N-methylnaphthalene-2-sulfonamide 、 1,4-dihydro-6-methoxy-N-methylnaphthalene-2-sulfonamide
  参考文献：
  名称：

  萘磺酰胺的金属氨还原和还原烷基化。取代萘的新途径。

  摘要：

  已经发现成功地使N-烷基芳基磺酰胺的Birch还原和还原性烷基化的条件，特别是在萘系列中。衍生的C-烷基化产物在加热后随着重新芳构化而平滑地断裂，从而提供了一条新的特定路线，从1-磺酰胺类化合物到1-取代的萘，再到2-单取代和2,4-（或1,3） -）来自相应的2-磺酰胺的二取代的萘。

  DOI：

  10.1016/s0040-4039(00)80526-2

文献信息

• Metal-ammonia reduction and reductive alkylation of N-alkylnaphthalenesulfonamides. A new route to substituted naphthalenes
  作者：H. J. E. Loewenthal、L. Gottlieb

  DOI：10.1021/jo00035a018

  日期：1992.4

  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.