N-((2-hydroxynaphthalen-1-yl)methyl)benzamide | 69025-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-((2-hydroxynaphthalen-1-yl)methyl)benzamide
• 英文别名: 1-Benzamidomethyl-2-naphthol；Benzamide, N-[(2-hydroxy-1-naphthalenyl)methyl]-；N-[(2-hydroxynaphthalen-1-yl)methyl]benzamide
• CAS: 69025-33-8
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: BTWZPFYRWQFDCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  N-((2-hydroxynaphthalen-1-yl)methyl)benzamide 在 硫酸 、 碘 、 sulfur 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 7.5h， 生成 11-(Benzamidomethyl)-12-(nicotinamidomethyl)-12H-benzophenothiazine
  参考文献：
  名称：

  Pandey, V. K.; Garg, Punita; Ram, Shiv, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1208 - 1210

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(benzoylamino-methyl)-2-benzoyloxy-naphthalene 以72%的产率得到
  参考文献：
  名称：

  MOEHRLE H.; LAPPENBERG M., ARCH. PHARM., 1978, 311, NO 11, 897-906

  摘要：

  DOI：

文献信息

• [EN] FORMAMIDE DERIVATIVES USEFUL AS ADRENOCEPTOR<br/>[FR] DERIVES DE FORMAMIDE UTILES COMME RECEPTEURS ADRENERGIQUES
  申请人：PFIZER LTD

  公开号：WO2005092840A1

  公开（公告）日：2005-10-06

  The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  该发明涉及公式（1）的化合物，以及用于制备、用于制备的中间体、含有和用途的过程。根据本发明的化合物在许多疾病、紊乱和情况中都有用，特别是在炎症、过敏和呼吸系统疾病、紊乱和情况中。
• Spirooxazoline Synthesis by an Oxidative Dearomatizing Cyclization
  作者：M. Umair Tariq、Wesley J. Moran

  DOI：10.1002/ejoc.202000840

  日期：2020.8.31

  The oxidative spirocyclization of phenols and naphthols containing pendent amides is described that grants access to unusual spirooxazoline compounds. These rare spirocycles are prepared by an iodine(I)/(III) catalytic cycle.

  描述了含侧基酰胺的苯酚和萘酚的氧化螺环化，可以接触到不常见的螺恶唑啉化合物。这些稀有螺环是通过碘（I）/（III）催化循环制备的。
• Application of chiral triazole-substituted iodoarenes in the enantioselective construction of spirooxazolines
  作者：Ayham H. Abazid、Boris J. Nachtsheim

  DOI：10.1039/d1cc03246a

  日期：——

  A catalytic highly enantioselective synthesis of spirooxazolines is presented. Starting from readily available 2-naphthol-substituted benzamides and using catalytic amounts of a chiral triazole-substituted iodoarene catalyst, a variety of spirooxazolines can be isolated through an enantioselective oxidative dearomatization in up to 92% yield and 97% ee. The further synthetic utility of the optically

  介绍了螺恶唑啉的催化高度对映选择性合成。从容易获得的 2-萘酚取代的苯甲酰胺开始，并使用催化量的手性三唑取代的碘芳烃催化剂，可以通过对映选择性氧化脱芳构化以高达 92% 的产率和 97% 的 ee 分离各种螺恶唑啉。研究了光学富集的螺恶唑啉的进一步合成效用，提供了相应的 2-萘酚和恶唑平。
• Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl‐Based λ ³ ‐Iodanes
  作者：Huaiyuan Zhang、Rodrigo A. Cormanich、Thomas Wirth

  DOI：10.1002/chem.202103623

  日期：2022.1.24

  Contained chirality: Novel binaphthyl-based chiral hypervalent iodine(III) reagents are presented with the chirality contained only in the ligand. These have been characterized by X-ray analysis, and all derivatives show the prominent reactivities of hypervalent iodine reagents. Due to their limited stability in solution, they are inefficient chiral iodine(III) derivatives.

  包含手性：新型基于联萘的手性高价碘（III）试剂具有仅包含在配体中的手性。这些已通过 X 射线分析进行了表征，并且所有衍生物都显示出高价碘试剂的突出反应性。由于它们在溶液中的稳定性有限，它们是低效的手性碘 (III) 衍生物。
• Synthesis of 1-Amidoalkyl-2-Naphthols by Two-Component Friedel-Crafts Reaction
  作者：Li-Ping Liu、Liang-Min Yu、Zhi-Ming Zhang、Xue-Feng Yan

  DOI：10.14233/ajchem.2013.14087

  日期：——

  A one-pot two-component Friedel-Crafts reaction of 1-amidoalkyl-2-naphthols by the condensation of 2-naphthol with various N-methyl hydrocarbon unsaturated amides in presence of the concentrated sulphuric acid as catalyst and anhydrous ethyl alcohol as solvent to form the corresponding amidoalkyl naphthols is described. This procedure offers advantages such as eco-friendly, shorter reaction times, simple work-up, excellent yields and recovery and reusability of the catalyst. The spectroscopic properties are assessed for their effectiveness and the fluorescent intensity sequence of three compounds in two different solvents follows the sequence: 1-N-methacrylamide-2-naphthol > 1-N-methy phthalimide-2-naphthol > 1-N-methy phthalimide-2-naphthol.

  描述了一种一锅两组分的弗里德尔-克拉夫茨反应，通过将2-萘醇与各种N-甲基碳氢链不饱和酰胺在浓硫酸催化剂和无水乙醇溶剂的存在下进行缩合，形成相应的酰胺烷基萘醇。该程序具有生态友好、反应时间短、操作简单、产率优异以及催化剂的回收和重复使用等优点。对其光谱性质进行了评估，结果表明在两种不同溶剂中三种化合物的荧光强度顺序为：1-N-甲基丙烯酰胺-2-萘醇 > 1-N-甲基邻苯二甲酰亚胺-2-萘醇 > 1-N-甲基邻苯二甲酰亚胺-2-萘醇。