N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-1-benzothiophene-2-carboxamide | 541549-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-1-benzothiophene-2-carboxamide
• CAS: 541549-91-1
• 化学式: C₁₄H₁₇NO₂S
• mdl: MFCD23276247
• 分子量: 263.36
• InChiKey: WUFUOONZQFKIIT-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-1-benzothiophene-2-carboxamide 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-2-(1-benzothiophen-2-yl)-4-isopropyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Synthesis of new sulfur-containing oxazoline ligands and their use in palladium-catalyzed allylic substitution

  摘要：

  New chiral sulfur-containing ligands have been prepared and fully characterized. Their structure includes a dibenzothiophene or benzothiophene ring as backbone, where the sulfur atom is enclosed in a strong pi-donor structure. The chirality was introduced by oxazoline moieties placed near the sulfur atom. These ligands have been successfully tested in asymmetric palladium-catalyzed allylic substitutions leading to products with ee of up to 77%. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00829-7
• 作为产物：
  描述：

  苯并噻吩-2-羧酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 2.5h， 生成 N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-1-benzothiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis of new sulfur-containing oxazoline ligands and their use in palladium-catalyzed allylic substitution

  摘要：

  New chiral sulfur-containing ligands have been prepared and fully characterized. Their structure includes a dibenzothiophene or benzothiophene ring as backbone, where the sulfur atom is enclosed in a strong pi-donor structure. The chirality was introduced by oxazoline moieties placed near the sulfur atom. These ligands have been successfully tested in asymmetric palladium-catalyzed allylic substitutions leading to products with ee of up to 77%. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00829-7

文献信息

• Synthesis of new sulfur-containing oxazoline ligands and their use in palladium-catalyzed allylic substitution
  作者：Arnaud Voituriez、Emmanuelle Schulz

  DOI：10.1016/s0957-4166(02)00829-7

  日期：2003.2

  New chiral sulfur-containing ligands have been prepared and fully characterized. Their structure includes a dibenzothiophene or benzothiophene ring as backbone, where the sulfur atom is enclosed in a strong pi-donor structure. The chirality was introduced by oxazoline moieties placed near the sulfur atom. These ligands have been successfully tested in asymmetric palladium-catalyzed allylic substitutions leading to products with ee of up to 77%. (C) 2003 Elsevier Science Ltd. All rights reserved.