1-(4-丁氧基苯基)丙烷-1-酮 | 5736-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-丁氧基苯基)丙烷-1-酮
• 英文名称: 1-(4-butoxyphenyl)propan-1-one
• CAS: 5736-90-3
• 化学式: C₁₃H₁₈O₂
• mdl: MFCD02176687
• 分子量: 206.285
• InChiKey: DGRPJRSRLYATME-UHFFFAOYSA-N

物化性质

• 熔点：
  29 °C
• 沸点：
  199-200 °C(Press: 32 Torr)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  1-(4-丁氧基苯基)丙烷-1-酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2-Diethylamino-ethyl)-<1-(4-butyloxy-phenyl)-propyl>-ether
  参考文献：
  名称：

  ROHMANN; MEISEL, Archiv der Pharmazie, 1961, vol. 294 /66, p. 538 - 549

  摘要：

  DOI：
• 作为产物：
  描述：

  1-碘丁烷 、 4-羟基苯丙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以93%的产率得到1-(4-丁氧基苯基)丙烷-1-酮
  参考文献：
  名称：

  Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors

  摘要：

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.

  DOI：

  10.1021/jm020557k

文献信息

• Cu-Catalyzed Sequential Dehydrogenation–Conjugate Addition for β-Functionalization of Saturated Ketones: Scope and Mechanism
  作者：Xiaoming Jie、Yaping Shang、Xiaofeng Zhang、Weiping Su

  DOI：10.1021/jacs.6b01337

  日期：2016.5.4

  The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible

  报道了第一个铜催化的饱和酮直接β-官能化。该协议使不同的酮能够在操作简单的条件下以通常良好的产率与广泛的氮、氧和碳亲核试剂结合。进行了详细的机理研究，包括动力学研究、KIE 测量、反应中间体的鉴定、EPR 和紫外可见实验，结果表明该反应是通过一种新型的基于自由基的脱氢生成烯酮和随后的共轭加成序列进行的。
• Site-Specific Oxidation of (sp³)C–C(sp³)/H Bonds by NaNO₂/HCl
  作者：Jianyou Zhao、Tong Shen、Zhihui Sun、Nengyong Wang、Le Yang、Jintao Wu、Huichao You、Zhong-Quan Liu

  DOI：10.1021/acs.orglett.1c01303

  日期：2021.5.21

  (sp3)C–C(sp3) and (sp3)C–H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.

  通过使用NaNO 2 / HCl ，对芳基烷烃中的（sp 3）C–C（sp 3）和（sp 3）C–H键进行了位点特异性氧化的研究。该方法无化学氧化剂，无过渡金属，以水为溶剂，在温和条件下进行，使其对合成有机化学有价值且具有吸引力。
• Catalytic Friedel–Crafts Acylation of Alkoxybenzenes Mediated by Aluminum Hydrogensulfate in Solution and Solvent-Free Conditions
  作者：Peyman Salehi、Mohammad Mehdi Khodaei、Mohammad Ali Zolfigol、Sara Sirouszadeh

  DOI：10.1246/bcsj.76.1863

  日期：2003.9

  Friedel–Crafts acylation of alkoxybenzenes was achieved efficiently by a reaction with aliphatic acid anhydrides in the presence of catalytic amounts of aluminum hydrogensulfate, Al(HSO4)3, in nitromethane and under solvent-free conditions. Alkylbenzenes and aryl halides, as well as aromatic anhydrides, remained intact under these conditions.

  在催化量的硫酸氢铝 Al(HSO4)3 存在下，在硝基甲烷和无溶剂条件下，通过与脂肪酸酐反应，有效地实现烷氧基苯的 Friedel-Crafts 酰化。在这些条件下，烷基苯和芳基卤化物以及芳族酸酐保持完整。
• Catalytic Friedel–Crafts Acylation of Alkoxy Benzenes by Ferric Hydrogensulfate
  作者：Peyman Salehi、Mohammad Mahdi Khodaei、Mohammad Ali Zolfigol、Shahpour Zeinoldini

  DOI：10.1081/scc-120018697

  日期：2003.1.5

  Abstract Friedel–Crafts acylation of alkoxy benzenes is achieved efficiently by reaction with aliphatic acid anhydrides in the presence of catalytic amounts of ferric hydrogensulfate, Fe(HSO4)3, in nitromethane. Alkyl benzenes and aryl halides, as well as aromatic anhydrides, remain intact under these conditions.

  摘要 在硝基甲烷中，在催化量的硫酸氢铁 Fe(HSO4)3 存在下，通过与脂肪酸酐反应，可以有效地实现烷氧基苯的 Friedel-Crafts 酰化。烷基苯和芳基卤化物以及芳香酸酐在这些条件下保持完整。
• [EN] 3-(2-AMINO-ETHYL)-ALKYLIDENE)-THIAZOLIDINE-2,4-DIONE AND 1-(2-AMINO-ETHYL)-ALKYLIDENE-1,3-DIHYDRO-INDOL-2-ONE DERIVATIVES AS SELECTIVE SPHINGOSINE KINASE 2 INHIBITORS<br/>[FR] DÉRIVÉS DE 3-(2-AMINO-ÉTHYL)-ALKYLIDÈNE)-THIAZOLIDINE-2,4-DIONE ET 1-(2-AMINO-ÉTHYL)-ALKYLIDÈNE-1,3-DIHYDRO-INDOL-2-ONE EN TANT QU'INHIBITEURS SÉLECTIFS DE LA SPHINGOSINE KINASE 2
  申请人：UNIV VIRGINIA COMMONWEALTH

  公开号：WO2013119774A1

  公开（公告）日：2013-08-15

  3-(2-amino-ethyl)-5-[3-(4-substituted-phenyl)-alkylidene)-thiazolidine-2,4-dione and l-(2-amino-ethyl)-3-alkylidene-l,3-dihydro-indol-2-one and derivatives thereof are provided for use as selective SphK2 inhibitors and for use in the treatment of human diseases, such as cancer.

  提供用作选择性SphK2抑制剂以及用于治疗人类疾病（如癌症）的3-(2-氨基乙基)-5-[3-(4-取代苯基)-烷基亚乙烯基)-噻唑啉-2,4-二酮和l-(2-氨基乙基)-3-烷基亚乙烯基-1,3-二氢吲哚-2-酮及其衍生物。