1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene | 132912-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene
• 英文别名: 2-(1'-Naphthyl)-4-(S)-tert-butyloxazoline；(4S)-4-tert-butyl-2-naphthalen-1-yl-4,5-dihydro-1,3-oxazole
• CAS: 132912-17-5
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: TUDDRCTWVWDTFC-OAHLLOKOSA-N

物化性质

• 沸点：
  391.2±11.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

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：

  1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene 在 盐酸 、 六甲基磷酰三胺 、 正丁基锂 作用下， 反应 5.08h， 生成 (1R,2S)-1-Allyl-2-piperidin-1-yl-1,2-dihydro-naphthalene-1-carboxylic acid (S)-2-amino-3,3-dimethyl-butyl ester
  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-萘甲酰氯 在 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene
  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

文献信息

• Highly reactive organolithiums (from “Freeman's Reagent”) and their additions to naphthalene oxazolines.
  作者：David J. Rawson、A.I. Meyers

  DOI：10.1016/s0040-4039(00)71245-7

  日期：1991.5

  Generation of organolithium reagents using lithio ditert-butyl biphenyl (Freeman's Reagent) leads to facile additions to the naphthalene oxazolines.

  使用硫代二叔丁基联苯（Freeman试剂）生成有机锂试剂可轻松添加到萘恶唑啉中。
• Enantioselective Synthesis of Rigid 2-Aminotetralins. Utility of Silicon as an Oxygen and Nitrogen Surrogate in the Tandem Addition Reaction
  作者：Andrew P. Degnan、A. I. Meyers

  DOI：10.1021/jo0001131

  日期：2000.6.1

  Dimethylphenylsilyllithium undergoes a highly diastereoselective conjugate addition to chiral naphthyloxazoline 11. Electrophilic trapping of the resulting aza-enolate affords the tandem addition product (12) in high yields as a single diastereomer. The silicon, thus incorporated, may be protodesilylated and undergoes a Tamao oxidation to afford the corresponding alcohol. By chemical modification of the oxazoline

  二甲基苯基甲硅烷基锂经历手性萘基恶唑啉11的高度非对映选择性共轭加成反应。亲电捕集所得的氮杂-烯醇酸酯可作为单个非对映异构体以高收率获得串联加成产物（12）。这样掺入的硅可以被去甲硅烷基化并进行塔毛氧化以提供相应的醇。通过恶唑啉的化学改性，制备了γ-内酯（28）和δ-内酯（37）。还原每种内酯，然后氧化随后的二醇，得到酮醛。1,4-二羰基的双还原胺化（来自γ-内酯）允许合成两个新颖的六氢苯并[e]吲哚，20和35。1,5-二羰基的双还原胺化（来自δ-内酯）接触了两种新颖的八氢苯并[f]喹啉，
• 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.
• Asymmetric Synthesis of 1,1-Disubstituted Tetralins and Dihydronaphthalenes by Diastereoselective Addition of Lithiosilanes to Chiral Naphthalenes
  作者：Alison N. Hulme、A. I. Meyers

  DOI：10.1021/jo00084a007

  日期：1994.3

  Highly diastereoselective additions of lithiosilanes to chiral naphthalenes can be performed in ether/THF. Trapping of the resulting azaenolate, followed by protodesilylation, allows access to 1,1-disubstituted tetralins or dihydronaphthalenes in good yields and high enantiomeric excess.