O-isopropyl 5-chloro-2-methoxyphenylthiocarbamate | 869278-94-4

• 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: O-isopropyl 5-chloro-2-methoxyphenylthiocarbamate
• 英文别名: O-propan-2-yl N-(5-chloro-2-methoxyphenyl)carbamothioate
• CAS: 869278-94-4
• 化学式: C₁₁H₁₄ClNO₂S
• 分子量: 259.757
• InChiKey: NFFLGQZAFHBOIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-isopropyl 5-chloro-2-methoxyphenylthiocarbamate 、 N,N-二甲基甲酰胺 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 3.0h， 以26%的产率得到O-isopropyl 5-chloro-3-formyl-2-methoxyphenylthiocarbamate
  参考文献：
  名称：

  Synthesis of the Marine Sponge Derived β₂-Adrenoceptor Agonist S1319

  摘要：

  The marine sponge derived beta 2-adrenoceptor agonist S1319 has been synthesized following a six-step linear sequence. Central to the approach employed is the formation of a 7-lithiated-2,4-dialkoxybenzothiazole intermediate obtained via a directed-lithiation/benzyne-mediated cyclization reaction. The incorporation of a tert-butyl ether residue into the cyclization precursor for the pivotal ring-closing step has been shown to significantly increase the efficiency of the reaction by the suppression of a competing directed ortho-lithiation reaction.

  DOI：

  10.1021/ol0518840
• 作为产物：
  描述：

  4-chloro-2-isothiocyanato-1-methoxybenzene 、 异丙醇 在 三乙胺 作用下， 以94%的产率得到O-isopropyl 5-chloro-2-methoxyphenylthiocarbamate
  参考文献：
  名称：

  Synthesis of the Marine Sponge Derived β₂-Adrenoceptor Agonist S1319

  摘要：

  The marine sponge derived beta 2-adrenoceptor agonist S1319 has been synthesized following a six-step linear sequence. Central to the approach employed is the formation of a 7-lithiated-2,4-dialkoxybenzothiazole intermediate obtained via a directed-lithiation/benzyne-mediated cyclization reaction. The incorporation of a tert-butyl ether residue into the cyclization precursor for the pivotal ring-closing step has been shown to significantly increase the efficiency of the reaction by the suppression of a competing directed ortho-lithiation reaction.

  DOI：

  10.1021/ol0518840