2-(2'-Naphthyl)-4-(S)-tert-butyloxazoline | 132912-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2'-Naphthyl)-4-(S)-tert-butyloxazoline
• 英文别名: (4S)-4-tert-butyl-2-naphthalen-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 132912-25-5
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: LADFHGFFBSQSLB-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2'-Naphthyl)-4-(S)-tert-butyloxazoline 在 盐酸 、 六甲基磷酰三胺 、 正丁基锂 作用下， 反应 5.41h， 生成 1-[(1S,2R)-2-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1,2-dihydro-naphthalen-1-yl]-piperidin-4-one
  参考文献：
  名称：

  Asymmetric Diastereoselective Conjugate Additions of Lithium Amides to Chiral Naphthyloxazolines Leading to Novel .beta.-Amino Acids

  摘要：

  The functionalization of the naphthalene ring system by a direct amination-alkylation reaction of chiral nonracemic naphthyloxazolines is described. Chiral 1-naphthyl- and 2-naphthyloxazoline were treated with a variety of lithium amides followed by several different electrophilic quenches. The solvent and additives were varied in. order to achieve optimum conditions. The combination of HMPA and THF at -78 degrees C gave the best yield with excellent stereoselectivity. The present methodology provides a stereospecific synthesis of novel, nonracemic, rigid beta-amino acids after hydrolytic removal of the chiral oxazoline.

  DOI：

  10.1021/jo00128a016
• 作为产物：
  描述：

  1-bromo-2-naphthoyl chloride 在 吡啶 、 铜 作用下， 反应 24.0h， 生成 2-(2'-Naphthyl)-4-(S)-tert-butyloxazoline
  参考文献：
  名称：

  The Asymmetric Ullmann Reaction. 2. The Synthesis of Enantiomerically Pure C2-Symmetric Binaphthyls

  摘要：

  DOI：

  10.1021/jo00088a066

文献信息

• Shimano, Masanao; Meyers, Journal of the American Chemical Society, 1994, vol. 116, # 14, p. 6437 - 6438
  作者：Shimano, Masanao、Meyers

  DOI：——

  日期：——
• Asymmetric tandem additions to chiral naphthyloxazolines. A new and potent chiral auxiliary resulting in a major improvement in convenience and efficiency
  作者：David J. Rawson、A. I. Meyers

  DOI：10.1021/jo00007a010

  日期：1991.3

  Excellent diastereofacial selectivities over a wide range of temperatures (-78 to 25-degrees-C) were obtained with the title compounds with use of chiral oxazolines derived from (S)-valinol or (S)-tert-leucinol. These are the first useful levels of asymmetric induction observed without the presence of the chelating methoxyl groups. The dihydronaphthylcarbinols and aldehydes resulting from these additions were obtained in > 98% ee.
• RAWSON, DAVID J.;MEYERS, A. I., J. ORG. CHEM., 56,(1991) N, C. 2292-2294
  作者：RAWSON, DAVID J.、MEYERS, A. I.

  DOI：——

  日期：——
• Nelson Todd D., Meyers A. I., J. Org. Chem, 59 (1994) N 9, S 2655- 2658
  作者：Nelson Todd D., Meyers A. I.

  DOI：——

  日期：——
• Shimano Masanao, Meyers A. I., J. Amer. Chem. Soc, 116 (1994) N 14, S 6437- 6438
  作者：Shimano Masanao, Meyers A. I.

  DOI：——

  日期：——