3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)naphthalen-2-ol | 1609242-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)naphthalen-2-ol
• CAS: 1609242-51-4
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: YLSOJZKNGOJBPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)naphthalen-2-ol 、 (NBu4)[ReOCl4] 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以25%的产率得到chlorobis(3-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2-naphtholato)oxorhenium(V)
  参考文献：
  名称：

  Oxorhenium(V) complexes with naphtholate-oxazoline ligands in the catalytic epoxidation of olefins

  摘要：

  Four oxorhenium(V) complexes 3a-d equipped with naphtholate-oxazoline based ligands 2a-d have been prepared and characterized by NMR, IR and mass spectroscopy as well as elemental analysis. Ligands 2a-d were prepared in a two-step procedure from commercially available starting materials. Ligands 2a-b and 2c-d are regioisomers to each other regarding the position of the -OH group and oxazoline moiety on the naphthol ring. Reaction of 2a-d with (NBu4)[ReOCl4] in methanol under reflux gave oxorhenium(V) complexes 3a-d of the type [ReOCl(L)(2)] as green solids in acceptable to good yields. The molecular structures of complexes 3b and 3d have been determined via single crystal X-ray diffraction analysis and both display a distorted octahedral geometry. Complexes 3a-d are active catalysts for the epoxidation of cyclooctene with tert-butylhydroperoxide (TBHP) showing moderate conversions between 41% and 65%. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.024
• 作为产物：
  描述：

  3-hydroxy-N-(1-hydroxy-2-methylpropan-2-yl)naphthalene-2-carboxamide 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)naphthalen-2-ol
  参考文献：
  名称：

  Oxorhenium(V) complexes with naphtholate-oxazoline ligands in the catalytic epoxidation of olefins

  摘要：

  Four oxorhenium(V) complexes 3a-d equipped with naphtholate-oxazoline based ligands 2a-d have been prepared and characterized by NMR, IR and mass spectroscopy as well as elemental analysis. Ligands 2a-d were prepared in a two-step procedure from commercially available starting materials. Ligands 2a-b and 2c-d are regioisomers to each other regarding the position of the -OH group and oxazoline moiety on the naphthol ring. Reaction of 2a-d with (NBu4)[ReOCl4] in methanol under reflux gave oxorhenium(V) complexes 3a-d of the type [ReOCl(L)(2)] as green solids in acceptable to good yields. The molecular structures of complexes 3b and 3d have been determined via single crystal X-ray diffraction analysis and both display a distorted octahedral geometry. Complexes 3a-d are active catalysts for the epoxidation of cyclooctene with tert-butylhydroperoxide (TBHP) showing moderate conversions between 41% and 65%. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.024

文献信息

• Aerobic C(sp²)–H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
  作者：Dominik Göbel、Nils Clamor、Enno Lork、Boris J. Nachtsheim

  DOI：10.1021/acs.orglett.9b01350

  日期：2019.7.19

  The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl center dot LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.