1-(naphthalen-1-yl)pentan-2-one | 861936-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-1-yl)pentan-2-one
• 英文别名: 1-Naphthalen-1-ylpentan-2-one
• CAS: 861936-56-3
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: HRKGXSSNSJAHNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(naphthalen-1-yl)pentan-2-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

  摘要：

  AbstractNitrogen‐substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper‐catalyzed synthesis of ynimines from readily available O‐acetyl ketoximes and terminal alkynes. A wide range of O‐acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross‐coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.

  DOI：

  10.1002/anie.202110901
• 作为产物：
  描述：

  1-萘乙酸 在 copper(l) iodide 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 1-(naphthalen-1-yl)pentan-2-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 4-hydroxypyrone derivatives as HIV-1 protease inhibitors

  摘要：

  Twenty-four 4-hydroxypyrone derivatives were synthesized with a facile synthetic method to develop novel HIV protease inhibitors. Most of them were shown to display good antiviral activities in SIV-infected CEM cells. The introduction of alpha-naphthylmethyl group to C-6 of 5,6-dihydropyran-2-ones led to an effective antiviral compound that showed an EC50 value at 1.7 mu M with a therapeutic index of 46. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.057

文献信息

• Process for producing highly pure aromatic polycarboxylic acid
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：EP1055660A1

  公开（公告）日：2000-11-29

  Highly pure, less colored aromatic polycarboxylic acids are produced from crude aromatic polycarboxylic acids by simple procedures at low production costs. The crude aromatic polycarboxylic acid is mixed with aliphatic amine or alicyclic amine in the presence of a solvent to precipitate crystals of amine salt of aromatic polycarboxylic acid. The crystals are dissolved in water and decomposed, thereby obtaining the highly pure aromatic polycarboxylic acids.

  高纯度、低色度的芳香族聚羧酸可通过简单的程序以较低的生产成本从粗芳香族聚羧酸中生产出来。在有溶剂存在的情况下，将粗芳香族聚羧酸与脂肪族胺或脂环族胺混合，析出芳香族聚羧酸胺盐晶体。将晶体溶于水并分解，从而得到高纯度的芳香族聚羧酸。
• US6452047B1
  申请人：——

  公开号：US6452047B1

  公开（公告）日：2002-09-17
• US8993799B2
  申请人：——

  公开号：US8993799B2

  公开（公告）日：2015-03-31
• Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles
  作者：Rémi Lavernhe、Rubén O. Torres‐Ochoa、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202110901

  日期：2021.11.2

  AbstractNitrogen‐substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper‐catalyzed synthesis of ynimines from readily available O‐acetyl ketoximes and terminal alkynes. A wide range of O‐acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross‐coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.
• Design, synthesis, and biological evaluation of novel 4-hydroxypyrone derivatives as HIV-1 protease inhibitors
  作者：Chun-Lai Sun、Rui-Fang Pang、Hang Zhang、Ming Yang

  DOI：10.1016/j.bmcl.2005.04.057

  日期：2005.7

  Twenty-four 4-hydroxypyrone derivatives were synthesized with a facile synthetic method to develop novel HIV protease inhibitors. Most of them were shown to display good antiviral activities in SIV-infected CEM cells. The introduction of alpha-naphthylmethyl group to C-6 of 5,6-dihydropyran-2-ones led to an effective antiviral compound that showed an EC50 value at 1.7 mu M with a therapeutic index of 46. (c) 2005 Elsevier Ltd. All rights reserved.