benzyl N-hydroxynaphthalene-2-carbimidothioate | 13750-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzyl N-hydroxynaphthalene-2-carbimidothioate
• 英文别名: S-Benzyl-naphthalin-2-thiohydroxamsaeure
• CAS: 13750-04-4
• 化学式: C₁₈H₁₅NOS
• 分子量: 293.389
• InChiKey: JMBFIFFKPHXONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl N-hydroxynaphthalene-2-carbimidothioate 在 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以72%的产率得到3-(naphthalen-2-yl)-5-phenyl-1,4,2-oxathiazole
  参考文献：
  名称：

  Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids

  摘要：

  An oxidative formation of 1,4,2-oxathiazoles from readily available thiohydroximic acids is reported. A variety of alkyl, aryl, and heteroaryl substituents are well tolerated for both the thiohydroximic acid and activating fragments, and the reaction has been demonstrated on gram-scale. This reaction represents the only method currently available to prepare a diverse set of oxathiazoles and expands the chemistry of C-H oxidation via appended N-OH functional groups. Finally, we also demonstrate the rapid preparation of a 1,4,2-oxathiazole analog of an anticancer lead molecule.

  DOI：

  10.1021/acs.orglett.5b02256
• 作为产物：
  描述：

  2-萘甲醛 在 吡啶 、 N-氯代丁二酰亚胺 、 盐酸羟胺 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 benzyl N-hydroxynaphthalene-2-carbimidothioate
  参考文献：
  名称：

  Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids

  摘要：

  An oxidative formation of 1,4,2-oxathiazoles from readily available thiohydroximic acids is reported. A variety of alkyl, aryl, and heteroaryl substituents are well tolerated for both the thiohydroximic acid and activating fragments, and the reaction has been demonstrated on gram-scale. This reaction represents the only method currently available to prepare a diverse set of oxathiazoles and expands the chemistry of C-H oxidation via appended N-OH functional groups. Finally, we also demonstrate the rapid preparation of a 1,4,2-oxathiazole analog of an anticancer lead molecule.

  DOI：

  10.1021/acs.orglett.5b02256

文献信息

• Nagata,K.; Mizukami,S., Chemical and pharmaceutical bulletin, 1966, vol. 14, p. 1263 - 1272
  作者：Nagata,K.、Mizukami,S.

  DOI：——

  日期：——