benzyl N-hydroxybenzimidothioate | 725-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-hydroxybenzimidothioate
• 英文别名: thiobenzohydroximic acid benzyl ester；Thiobenzohydroximsaeure-benzylester；S-Benzyl-thiobenzhydroximsaeure；S-Benzyl-benzothiohydroxamsaeure；S-Benzyl-benzothiohydroximat
• CAS: 725-17-7
• 化学式: C₁₄H₁₃NOS
• 分子量: 243.329
• InChiKey: MDFBLHBTNYBDBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-hydroxybenzimidothioate 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到3,5-diphenyl-1,4,2-oxathiazole
  参考文献：
  名称：

  mid胺肟和硫代氢氧肟酸的氧化环化：一种简便有效的策略，用于获得3,5-二取代的1,2,4-恶二唑和1,4,2-恶二唑

  摘要：

  已经开发了一种简便实用的方案，分别通过室温下mid胺肟和硫代氢肟酸的氧化环化反应来合成3,5-二取代的1,2,4-恶二唑和1,4,2-恶二唑。使用温和的反应条件，廉价的试剂，广泛的底物范围以及良好至优异的产物收率是该方案的主要特征。

  DOI：

  10.1016/j.tetlet.2017.04.045
• 作为产物：
  描述：

  苯甲醛肟 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 benzyl N-hydroxybenzimidothioate
  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

• SYNTHESIS OF THIOHYDROXIMATES THE ADDITION OF THIOLS TO NITRILE OXIDES
  作者：M. H. Benn

  DOI：10.1139/v64-352

  日期：1964.11.1

  The addition of thiols to nitrile oxides is shown to constitute a general synthesis of thiohydroximates.

  向腈氧化物添加硫醇被证明构成了硫代羟基肟酸盐的一般合成。
• Cambi, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1909, vol. <5> 18 I, p. 688
  作者：Cambi

  DOI：——

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

  DOI：——

  日期：——
• Bacchetti; Alemagna, Rendiconti - Istituto Lombardo Accademia di Scienze e Lettere, A: Scienze Matematiche, Fisiche, Chimiche e Geologiche, 1957, vol. 91, p. 30,34
  作者：Bacchetti、Alemagna

  DOI：——

  日期：——
• Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids
  作者：Bérénice C. Lemercier、Joshua G. Pierce

  DOI：10.1021/acs.orglett.5b02256

  日期：2015.9.18

  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.