2-methoxy-1-(naphthalen-1-yl)ethanone | 40811-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxy-1-(naphthalen-1-yl)ethanone
• 英文别名: 2-methoxy-1-(naphthalen-1-yl)ethan-1-one；1-Methoxyacetyl-naphthalin；2-methoxy-1-[1]naphthyl-ethanone；2-Methoxy-1-[1]naphthyl-aethanon；2-Methoxy-1-naphthalen-1-ylethanone
• CAS: 40811-10-7
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: LBZZMNCUUCHTLL-UHFFFAOYSA-N

物化性质

• 沸点：
  184-186 °C(Press: 13 Torr)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-methoxy-1-(naphthalen-1-yl)ethanone 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 51.67h， 生成 ethyl 1-(2-methoxy-1-(naphthalen-1-yl)ethyl)piperidine-4-carboxylate
  参考文献：
  名称：

  X-ray Structural and Biological Evaluation of a Series of Potent and Highly Selective Inhibitors of Human Coronavirus Papain-like Proteases

  摘要：

  Structure-guided design was used to generate a series of noncovalent inhibitors with nanomolar potency against the papain-like protease (PLpro) from the SARS coronavirus (CoV). A number of inhibitors exhibit antiviral activity against SARS-CoV infected Vero E6 cells and broadened specificity toward the homologous PLP2 enzyme from the human coronavirus NL63. Selectivity and cytotoxicity studies established a more than 100-fold preference for the coronaviral enzyme over homologous human deubiquitinating enzymes (DUBs), and no significant cytotoxicity in Vero E6 and HEK293 cell lines is observed. X-ray structural analyses of inhibitor-bound crystal structures revealed subtle differences between binding modes of the initial benzodioxolane lead (15g) and the most potent analogues 3k and 3j, featuring a monofluoro substitution at para and meta positions of the benzyl ring, respectively. Finally, the less lipophilic bis(amide) 3e and methoxypyridine 5c exhibit significantly improved metabolic stability and are viable candidates for advancing to in vivo studies.

  DOI：

  10.1021/jm401712t
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 反应 8.0h， 以18%的产率得到2-methoxy-1-(naphthalen-1-yl)ethanone
  参考文献：
  名称：

  X-ray Structural and Biological Evaluation of a Series of Potent and Highly Selective Inhibitors of Human Coronavirus Papain-like Proteases

  摘要：

  Structure-guided design was used to generate a series of noncovalent inhibitors with nanomolar potency against the papain-like protease (PLpro) from the SARS coronavirus (CoV). A number of inhibitors exhibit antiviral activity against SARS-CoV infected Vero E6 cells and broadened specificity toward the homologous PLP2 enzyme from the human coronavirus NL63. Selectivity and cytotoxicity studies established a more than 100-fold preference for the coronaviral enzyme over homologous human deubiquitinating enzymes (DUBs), and no significant cytotoxicity in Vero E6 and HEK293 cell lines is observed. X-ray structural analyses of inhibitor-bound crystal structures revealed subtle differences between binding modes of the initial benzodioxolane lead (15g) and the most potent analogues 3k and 3j, featuring a monofluoro substitution at para and meta positions of the benzyl ring, respectively. Finally, the less lipophilic bis(amide) 3e and methoxypyridine 5c exhibit significantly improved metabolic stability and are viable candidates for advancing to in vivo studies.

  DOI：

  10.1021/jm401712t

文献信息

• Electrochemical Synthesis of α-Thiocyanated/Methoxylated Ketones Using Enol Acetates
  作者：Peng Zhang、Junwei Ma、Xuan Liu、Fei Xue、Yonghong Zhang、Bin Wang、Weiwei Jin、Yu Xia、Chenjiang Liu

  DOI：10.1021/acs.joc.3c01417

  日期：2023.12.1

  We have developed the synthesis of α-substituted ketone compounds with enol acetates in an electrochemical way. By using cheap NH4SCN and MeOH as the radical sources, a series of valuable α-thiocyanates/methoxy ketones were synthesized under mild electrolysis conditions in acceptable yields with diverse functional group compatibility. Additionally, the scale-up experiment and synthetic transformations

  我们开发了以电化学方式用烯醇乙酸酯合成α-取代酮化合物的方法。通过使用廉价的NH 4 SCN和MeOH作为自由基源，在温和的电解条件下合成了一系列有价值的α-硫氰酸酯/甲氧基酮，收率可接受，且具有多种官能团相容性。此外，放大实验和合成转化揭示了在有机合成中的潜在应用。
• Ridgway; Robinson, Journal of the Chemical Society, 1924, vol. 125, p. 218
  作者：Ridgway、Robinson

  DOI：——

  日期：——
• Synthetic Experiments in the Chrysene Series
  作者：Louis F. Fieser、Lloyd M. Joshel、Arnold M. Seligman

  DOI：10.1021/ja01877a046

  日期：1939.8
• US5880135A
  申请人：——

  公开号：US5880135A

  公开（公告）日：1999-03-09