Naphthalene-2-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide | 117052-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Naphthalene-2-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide
• 英文别名: N-(2-hydroxy-1,1-dimethylethyl)-2-naphthamide；N-(1-hydroxy-2-methylpropan-2-yl)naphthalene-2-carboxamide
• CAS: 117052-90-1
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: UPWOCWNNHCIXJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  Naphthalene-2-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4,4-dimethyl-2-(naphthalen-2-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  由芳基恶唑啉制备多官能化芳香腈

  摘要：

  来自恶唑啉的芳基腈：我们报道了一种制备高官能化三、四和五取代芳香腈的新方法，该方法通过在甲苯中使用s Bu 2 Mg 进行两次连续的镁化，然后与多种亲电子试剂发生捕获反应，然后使用草酰氯和催化量的 DMF（50 °C，4 小时）将恶唑基导向基团有效转化为腈官能团。

  DOI：

  10.1002/chem.202103700
• 作为产物：
  描述：

  2-萘甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 Naphthalene-2-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide
  参考文献：
  名称：

  将有机锂的区域和立体选择性加成到萘中。1,2-三取代和反-2-二取代的二氢萘的高效合成

  摘要：

  将多种有机锂试剂添加到1-萘恶唑啉和2-萘恶唑啉中，然后用亲电试剂捕集，可得到高产率的标题化合物。很高的立体选择性是本发明方法的特征，因为亲电试剂从与有机锂试剂进入相反的萘面进入。已经研究了许多有机锂，并且发现从四取代的锡烷原位生成有机锂提供了用于将亲核加成到萘中的优良试剂。恶唑啉的去除有效地导致了甲酰基或羟甲基-1,2-二氢萘。

  DOI：

  10.1016/s0040-4020(01)85942-1

文献信息

• Regio- and stereoselective addition of organolithiums to naphthalenes. an efficient synthesis of 11,2-trisubstituted and trans-2-disubstituted dihydronaphthalenes
  作者：A.I. Meyers、Kathryn A. Lutomski、Dominique Laucher

  DOI：10.1016/s0040-4020(01)85942-1

  日期：1988.1

  The addition of a variety of organolithium reagents to 1-napththyloxazolines and 2-naphthyloxazolines followed by trapping with electrophiles leads to high yields of the title compounds. Very high stereoselectivity characterizes the present process in that the electrophile enters from the naphthalene face opposite to the entry of the organolithium reagent. A number of organolithiums have been investigated

  将多种有机锂试剂添加到1-萘恶唑啉和2-萘恶唑啉中，然后用亲电试剂捕集，可得到高产率的标题化合物。很高的立体选择性是本发明方法的特征，因为亲电试剂从与有机锂试剂进入相反的萘面进入。已经研究了许多有机锂，并且发现从四取代的锡烷原位生成有机锂提供了用于将亲核加成到萘中的优良试剂。恶唑啉的去除有效地导致了甲酰基或羟甲基-1,2-二氢萘。
• Convenient Catalytic Synthesis and Assignment of the Absolute Configuration of Enantiomerically Pure Dihydronaphthalenes and Their Corresponding Epoxides
  作者：Torsten Linker、Frank Rebien、Gábor Tóth、András Simon、Jürgen Kraus、Gerhard Bringmann

  DOI：10.1002/(sici)1521-3765(19981002)4:10<1944::aid-chem1944>3.0.co;2-l

  日期：1998.10.2

  In this paper we report on the synthesis and kinetic resolution of 1,2-dihydronaphthalenes by Jacobsen epoxidation, which proceeds smoothly with good selectivity (k(rel)=6.3-9.1). The yields were conveniently adjusted by variation of the number of equivalents of MCPBA (m-chloroperoxybenzoic acid) as the terminal oxidant, to afford enantiomerically pure starting materials or epoxides after one recrystallization. Complete separation of the starting material and the epoxides was effected by HPLC with a chiral stationary phase. Interestingly, the Jacobsen epoxidations afford two diastereomers, whereas the reaction with MCPBA alone proceeds with high diastereoselectivity. This can be attributed to unfavorable steric interactions and a matched-mismatched pair in the transition states. The relative configuration of both diastereomers was elucidated by detailed NMR spectroscopy. Furthermore, the absolute configuration of all the products was established unequivocally by comparison of experimental and calculated circular dichroism (CD) spectra. Since the epoxides can be transformed into the etoposide skeleton in only three steps, the kinetic resolution described herein offers simple access to optically active derivatives of these important anticancer drugs.
• Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
  作者：A. Hess、H. C. Guelen、N. Alandini、A. Mourati、Y. C. Guersoy、P. Knochel

  DOI：10.1002/chem.202103700

  日期：2022.1.3

  Aryl nitriles from oxazolines: We report a new method for for preparing highly functionalized tri-, tetra- and penta-substituted aromatic nitriles by using two successive magnesiations with sBu2Mg in toluene followed by trapping reactions with a broad range of electrophiles followed by an efficient conversion of the oxazolyl-directing group to a nitrile function by using oxalyl chloride and catalytic

  来自恶唑啉的芳基腈：我们报道了一种制备高官能化三、四和五取代芳香腈的新方法，该方法通过在甲苯中使用s Bu 2 Mg 进行两次连续的镁化，然后与多种亲电子试剂发生捕获反应，然后使用草酰氯和催化量的 DMF（50 °C，4 小时）将恶唑基导向基团有效转化为腈官能团。
• Linker, Torsten; Peters, Karl; Peters, Eva-Maria, Angewandte Chemie, 1996, vol. 108, # 21, p. 2662 - 2664
  作者：Linker, Torsten、Peters, Karl、Peters, Eva-Maria、Rebien, Frank

  DOI：——

  日期：——

表征谱图