O-tert-butyl N-[2-(4-tert-butoxy-2-isopropoxybenzothiazol-7-yl)-2-hydroxyethyl]-N-methylcarbamate | 869279-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: O-tert-butyl N-[2-(4-tert-butoxy-2-isopropoxybenzothiazol-7-yl)-2-hydroxyethyl]-N-methylcarbamate
• 英文别名: tert-butyl N-[2-hydroxy-2-[4-[(2-methylpropan-2-yl)oxy]-2-propan-2-yloxy-1,3-benzothiazol-7-yl]ethyl]-N-methylcarbamate
• CAS: 869279-00-5
• 化学式: C₂₂H₃₄N₂O₅S
• 分子量: 438.588
• InChiKey: SSBMWVXOXOJOQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O-tert-butyl N-[2-(4-tert-butoxy-2-isopropoxybenzothiazol-7-yl)-2-hydroxyethyl]-N-methylcarbamate 在 三氟乙酸 作用下， 反应 6.5h， 生成 4-hydroxy-7-(1-hydroxy-2-methylaminoethyl)-3H-benzothiazol-2-one trifluoroacetate
  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：

  2-叔丁氧基-5-氟苯胺 在 叔丁基锂 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 、 正戊烷 为溶剂， 反应 2.5h， 生成 O-tert-butyl N-[2-(4-tert-butoxy-2-isopropoxybenzothiazol-7-yl)-2-hydroxyethyl]-N-methylcarbamate
  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

文献信息

• Synthesis of the Marine Sponge Derived β₂-Adrenoceptor Agonist S1319
  作者：Robin A. Fairhurst、Diana Janus、Annabel Lawrence

  DOI：10.1021/ol0518840

  日期：2005.10.1

  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.