8-Methoxynaphthalene-2-sulfonyl chloride | 139633-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-Methoxynaphthalene-2-sulfonyl chloride
• CAS: 139633-69-5
• 化学式: C₁₁H₉ClO₃S
• 分子量: 256.71
• InChiKey: RQNSYGRCYBKAAA-UHFFFAOYSA-N

物化性质

• 沸点：
  407.2±20.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-Methoxynaphthalene-2-sulfonyl chloride 、 叔丁胺 以92.2%的产率得到N-tert-butyl-8-methoxynaphthalene-2-sulfonamide
  参考文献：
  名称：

  通过核超载增强测量确定取代萘的结构

  摘要：

  通过案例研究描述了方法，该方法结合现代1 H NMR方法确定萘，尤其是萘磺酸衍生物衍生产品中取代基的方向。

  DOI：

  10.1016/s0040-4020(01)88771-8
• 作为产物：
  描述：

  4-羟基萘-1,3,6-三磺酸 在 sodium hydroxide 、 硫酸 、 sodium sulfate 作用下， 以 水 为溶剂， 反应 1.75h， 生成 8-Methoxynaphthalene-2-sulfonyl chloride
  参考文献：
  名称：

  通过核超载增强测量确定取代萘的结构

  摘要：

  通过案例研究描述了方法，该方法结合现代1 H NMR方法确定萘，尤其是萘磺酸衍生物衍生产品中取代基的方向。

  DOI：

  10.1016/s0040-4020(01)88771-8

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.