2-acetyl-1-methoxynaphthalene | 24764-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetyl-1-methoxynaphthalene
• 英文别名: 1-(1-methoxynaphthalen-2-yl)ethanone；1-Methoxy-2-acetonaphthone；1-methoxy-2-acetylnaphthalene；2-acetyl-1-methoxynaphthalin；Acetyl-methoxy-naphthalene
• CAS: 24764-46-3
• 化学式: C₁₃H₁₂O₂
• mdl: MFCD00510349
• 分子量: 200.237
• InChiKey: WCUHIVUVLKYTQK-UHFFFAOYSA-N

物化性质

• 熔点：
  50 °C
• 沸点：
  182-186 °C(Press: 20 Torr)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetyl-1-methoxynaphthalene 在 间氯过氧苯甲酸 、 硫酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 480.0h， 以65%的产率得到2-羟基1-甲氧基萘
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040
• 作为产物：
  描述：

  乙酸-1-萘酯 在 sodium hydroxide 、 三氯化铝 作用下， 生成 2-acetyl-1-methoxynaphthalene
  参考文献：
  名称：

  Fries, Chemische Berichte, 1921, vol. 54, p. 711

  摘要：

  DOI：

文献信息

• Solvent Affected Facile Synthesis of Hydroxynaphthyl Ketones: Lewis Acids Promoted Friedel–Crafts and Demethylation Reaction
  作者：Wan‐mei Li、Hu‐qin Lai、Zhong‐hua Ge、Cheng‐rong Ding、Ying Zhou

  DOI：10.1080/00397910701263692

  日期：2007.5.1

  Abstract Hydroxynaphthyl ketones were obtained with high yields under very mild conditions in the presence of AlCl3 via Friedel–Crafts acylation and demethylation from naphthyl ethers. Several Lewis acids were tested, and AlCl3 was the most efficient catalyst.

  摘要 在 AlCl3 存在下，通过 Friedel-Crafts 酰化和萘醚脱甲基化，在非常温和的条件下以高产率获得羟基萘基酮。测试了几种路易斯酸，AlCl3 是最有效的催化剂。
• [EN] 5-HT2B RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR 5-HT2B
  申请人：PHARMAGENE LAB LTD

  公开号：WO2005012263A1

  公开（公告）日：2005-02-10

  Compounds of formulae: (I), (II), (IIIa), (IIIb), (IVa) and (IVb): or a pharmaceutically acceptable salt thereof, for use as pharmaceuticals, in particular for the treatment of a condition alleviated by antagonism of a 5-HT2B receptor.

  化合物的分子式：（I）、（II）、（IIIa）、（IIIb）、（IVa）和（IVb）：或其药用可接受的盐，用作药物，特别用于治疗通过拮抗5-HT2B受体缓解的病症。
• Beyond Directed <i>ortho</i> Metalation: Ruthenium-Catalyzed Amide-Directed C_Ar–OMe Activation/Cross-Coupling Reaction of Naphthamides with Aryl Boronates
  作者：Yigang Zhao、Victor Snieckus

  DOI：10.1021/acs.orglett.5b01913

  日期：2015.10.2

  A new and general synthetic methodology for the construction of biaryl, heterobiaryl, and polyaryl molecules by the ruthenium-catalyzed cross-coupling of ortho-methoxy naphthamides with aryl boroneopentylates is described. The isomeric 1-MeO-2-naphthamides and 2-MeO-1-naphthamides furnish an expansive series of arylated naphthamides in excellent yields. Competition experiments showed the higher reactivity

  描述了一种新的通用合成方法，该方法通过钌催化邻甲氧基萘酰胺与芳基硼烷戊酸酯的交叉偶联来构建联芳基，杂联芳基和聚芳基分子。异构的1-MeO-2-萘酰胺和2-MeO-1-萘酰胺以优异的收率提供了一系列芳基化萘酰胺。竞争实验表明1-MeO-2-萘酰胺比2-MeO-苯甲酰胺具有更高的反应性。建立了C–O活化/交叉偶联与Suzuki–Miyaura反应之间的正交性。该方法提供了难以通过定向原位金属化制备的萘。
• 1-(Naphthylalkyl)-1H-imidazole derivatives, a new class of anticonvulsant agents
  作者：Keith A. M. Walker、Marshall B. Wallach、Donald R. Hirschfeld

  DOI：10.1021/jm00133a015

  日期：1981.1

  anticonvulsant activity has been demonstrated for a large number of 1-(naphthylalkyl)-1H-imidazoles containing a variety of functional groups in the alkylene bridge. The presence of a small oxygen function in the bridge, in general, confers a high therapeutic index between anticonvulsant and depressant activity. Clinical expectations are discussed for 1-(2-naphthoylmethyl)imidazole hydrochloride (5), which is

  对于在亚烷基桥中含有各种官能团的大量1-（萘基烷基）-1H-咪唑已显示出有效的抗惊厥活性。通常，桥中小的氧功能的存在在抗惊厥和抑郁活性之间赋予较高的治疗指数。讨论了1-（2-萘甲酰基甲基）咪唑盐酸盐（5）的临床期望，该盐正在开发用于人体测试。
• Metal‐Free, Base‐Promoted, Tandem Pericyclic Reaction: A One‐Pot Approach for Cycloheptane‐Annelated Chromones from γ‐Alkynyl‐1,3‐Diketones
  作者：Yi‐En Liang、Chih‐Yu Kan、Balaji D. Barve、Yao‐Haur Kuo、Hsu‐Wei Fang、Wen‐Tai Li

  DOI：10.1002/adsc.202100956

  日期：2022.1.18

  A microwave-assisted, base-promoted, tandem cyclization reaction strategy has been developed for the synthesis of cyclohepta[b]chromones and spiro cyclohepta[b]chromones. Readily accessible γ-alkynyl-1,3-diketones undergo intramolecular cyclization and 7-endo-trig carbocyclization to afford various cycloheptane-annelated chromones in one-pot reactions. This metal-free protocol also led to the generation

  已经开发了一种微波辅助、碱促进的串联环化反应策略，用于合成环庚[ b ]色酮和螺环庚[ b ]色酮。容易获得的 γ-alkynyl-1,3-diketones 经历分子内环化和 7- endo - trig碳环化，在一锅反应中提供各种环庚烷-annelated 色酮。这种无金属协议还导致产生具有新的 C-C 键和新的 C-O 键的多环。