(S)-4-tert-Butyl-2-((1S,2S)-2-butyl-1-methyl-1,2-dihydro-naphthalen-1-yl)-4,5-dihydro-oxazole | 132912-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4-tert-Butyl-2-((1S,2S)-2-butyl-1-methyl-1,2-dihydro-naphthalen-1-yl)-4,5-dihydro-oxazole
• 英文别名: (4S)-4-tert-butyl-2-[(1S,2S)-2-butyl-1-methyl-2H-naphthalen-1-yl]-4,5-dihydro-1,3-oxazole
• CAS: 132912-22-2
• 化学式: C₂₂H₃₁NO
• 分子量: 325.494
• InChiKey: CLXRQLUTLLTPOE-KPLVRAHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-4-tert-Butyl-2-((1S,2S)-2-butyl-1-methyl-1,2-dihydro-naphthalen-1-yl)-4,5-dihydro-oxazole 在 三氟甲烷磺酸甲酯 作用下， 反应 4.0h， 生成 (1S,2S)-2-butyl-1-methyl-2H-naphthalene-1-carbaldehyde
  参考文献：
  名称：

  Asymmetric tandem additions to chiral naphthyloxazolines. A new and potent chiral auxiliary resulting in a major improvement in convenience and efficiency

  摘要：

  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.

  DOI：

  10.1021/jo00007a010
• 作为产物：
  描述：

  正丁基锂 、 1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene 、 碘甲烷 反应 2.0h， 以99%的产率得到(S)-4-tert-Butyl-2-((1S,2S)-2-butyl-1-methyl-1,2-dihydro-naphthalen-1-yl)-4,5-dihydro-oxazole
  参考文献：
  名称：

  Asymmetric tandem additions to chiral naphthyloxazolines. A new and potent chiral auxiliary resulting in a major improvement in convenience and efficiency

  摘要：

  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.

  DOI：

  10.1021/jo00007a010

文献信息

• Asymmetric Diastereoselective Conjugate Additions of Lithium Amides to Chiral Naphthyloxazolines Leading to Novel .beta.-Amino Acids
  作者：Masanao Shimano、A. I. Meyers

  DOI：10.1021/jo00128a016

  日期：1995.11

  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.
• 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：——