(S)-4,5-dihydro-2-(2-naphthyl)-4-(phenylmethyl)oxazole | 1019107-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4,5-dihydro-2-(2-naphthyl)-4-(phenylmethyl)oxazole
• 英文别名: (S)-4-benzyl-2-(2-naphthyl)-1,3-oxazoline；(4S)-4-benzyl-2-naphthalen-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 1019107-72-2
• 化学式: C₂₀H₁₇NO
• 分子量: 287.361
• InChiKey: VHUTXZCZWOFQLS-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-3-(2-naphthoyl)-4-phenylmethyl-2-oxazolidinone 在 ammonium chloride 、 lithium iodide 、 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 18.0h， 以80%的产率得到(S)-4,5-dihydro-2-(2-naphthyl)-4-(phenylmethyl)oxazole
  参考文献：
  名称：

  Decarboxylative Isomerization of N-Acyl-2-oxazolidinones to 2-Oxazolines

  摘要：

  N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50 degrees C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

  DOI：

  10.1021/jo800076f

文献信息

• Bromotriphenylphosphonium Salt Promoted Tandem One-Pot Cyclization to Optically Active 2-Aryl-1,3-oxazolines
  作者：Haizhen Jiang、Shijie Yuan、Wen Wan、Kun Yang、Hongmei Deng、Jian Hao

  DOI：10.1002/ejoc.201000162

  日期：2010.8

  Optically active 2-aryl-1,3-oxazolines, such as aromatic carbocycles, heterocycle-binding 4-benzyl (or phenyl)-1,3-oxazolines and their 5-benzyl (or phenyl)-1,3-oxazoline isomers were successfully prepared through a bromotriphenylphosphonium salt promoted aziridine ring formation and ring opening sequential process involving tandem one-pot cyclization of chiral 2-amino-3-phenylpropanol or 2-amino-2-phenylethanol

  光学活性 2-芳基-1,3-恶唑啉，如芳香碳环、杂环结合的 4-苄基（或苯基）-1,3-恶唑啉及其 5-苄基（或苯基）-1,3-恶唑啉异构体是通过溴三苯基鏻盐成功制备促进氮丙啶环形成和开环顺序过程，包括手性 2-氨基-3-苯基丙醇或 2-氨基-2-苯基乙醇与各种芳族酸在甲苯中在 90°C 和温和的条件下串联一锅环化以优异的产量。这种串联过程的机制也得到了实验证实。
• Decarboxylative Isomerization of <i>N</i>-Acyl-2-oxazolidinones to 2-Oxazolines
  作者：Aaron E. May、Patrick H. Willoughby、Thomas R. Hoye

  DOI：10.1021/jo800076f

  日期：2008.4.1

  N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50 degrees C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.