(S)-N-(2-hydroxy-2,4-dimethylpentan-3-yl)-1-iodo-2-naphthamide | 1415764-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-N-(2-hydroxy-2,4-dimethylpentan-3-yl)-1-iodo-2-naphthamide
• 英文别名: N-[(3S)-2-hydroxy-2,4-dimethylpentan-3-yl]-1-iodonaphthalene-2-carboxamide
• CAS: 1415764-13-4
• 化学式: C₁₈H₂₂INO₂
• 分子量: 411.283
• InChiKey: MKYUGWGRXVSYCR-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-hydroxy-2,4-dimethylpentan-3-yl)-1-iodo-2-naphthamide 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以69%的产率得到(S)-2-(1-iodonaphthalen-2-yl)-4-isopropyl-5,5-dimethyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process

  摘要：

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

  DOI：

  10.1021/jo302393u
• 作为产物：
  描述：

  1-iodo-2-hydroxymethylnaphtalene 在 potassium permanganate 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 37.17h， 生成 (S)-N-(2-hydroxy-2,4-dimethylpentan-3-yl)-1-iodo-2-naphthamide
  参考文献：
  名称：

  Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process

  摘要：

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

  DOI：

  10.1021/jo302393u