8-methoxy-N-methylnaphthalene-2-sulfonamide | 139633-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-methoxy-N-methylnaphthalene-2-sulfonamide
• CAS: 139633-70-8
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: VDXWEKZYYSEDGY-UHFFFAOYSA-N

物化性质

• 沸点：
  427.0±37.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-methoxy-N-methylnaphthalene-2-sulfonamide 在 三溴化硼 作用下， 反应 1.83h， 生成 (8-Hydroxy-naphthalen-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  A new synthetic analogue of the bracken ultimate carcinogen: Elevation of stability and alteration of DNA alkylation site selectivity

  摘要：

  The benzodienone 4 as a stable analogue of the bracken ultimate carcinogen (2) has been designed and synthesized. In the reaction with DNA the compound 4 was found to give only the N-7 alkylated product of guanine and no N-3 alkylated product of adenine and reveal guanine-selective cleavage in contrast to the natural dienone 2. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00572-8
• 作为产物：
  描述：

  8-Methoxynaphthalene-2-sulfonyl chloride 、 甲胺 以 二氯甲烷 、 水 为溶剂， 以95%的产率得到8-methoxy-N-methylnaphthalene-2-sulfonamide
  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