1-(1-Butylnaphthalen-2-yl)ethanone | 1284218-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-Butylnaphthalen-2-yl)ethanone
• CAS: 1284218-48-9
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: KASMKYXUQFIFQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-acetyl-1-methoxynaphthalene 、 正丁基氯化镁 以 四氢呋喃 为溶剂， 以66%的产率得到1-(1-Butylnaphthalen-2-yl)ethanone
  参考文献：
  名称：

  格氏试剂直接置换乙烯基酯的烷氧基

  摘要：

  描述了从芳族和不饱和酯和酮的 β 位直接置换烷氧基。该反应具有化学和区域选择性，显示出广泛的底物范围。

  DOI：

  10.1021/jo102537n

文献信息

• Direct Displacement of Alkoxy Groups of Vinylogous Esters by Grignard Reagents
  作者：Anthony J. Brockway、Marcos González-López、James C. Fettinger、Jared T. Shaw

  DOI：10.1021/jo102537n

  日期：2011.5.6

  The direct displacement of alkoxy groups from the β position of aromatic and unsaturated esters and ketones is described. The reaction is chemo- and regioselective, displaying wide substrate scope.

  描述了从芳族和不饱和酯和酮的 β 位直接置换烷氧基。该反应具有化学和区域选择性，显示出广泛的底物范围。
• Synthesis of tetracyclines and analogues thereof
  申请人：President and Fellows of Harvard College

  公开号：US11192866B2

  公开（公告）日：2021-12-07

  The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The modular synthesis of tetracyclines and tetracycline analogs described provides an efficient and enantioselective route to a variety of tetracycline analogs and polycyclines previously inaccessible via earlier tetracycline syntheses and semi-synthetic methods. These analogs may be used as anti-microbial agents or anti-proliferative agents in the treatment of diseases of humans or other animals.

  过去 50 年来，四环素类抗生素在治疗传染病方面发挥了重要作用。然而，随着四环素类药物在人类和兽医领域使用的增加，许多以前对四环素类抗生素易感的生物产生了抗药性。所述四环素和四环素类似物的模块化合成提供了一种高效的对映选择性途径，可获得以前通过早期的四环素合成和半合成方法无法获得的各种四环素类似物和多环化合物。这些类似物可用作治疗人类或其他动物疾病的抗微生物剂或抗增殖剂。
• SYNTHESIS OF TETRACYCLINES AND ANALOGUES THEREOF
  申请人：President and Fellows of Harvard College

  公开号：US20190345116A1

  公开（公告）日：2019-11-14

  The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The modular synthesis of tetracyclines and tetracycline analogs described provides an efficient and enantioselective route to a variety of tetracycline analogs and polycyclines previously inaccessible via earlier tetracycline syntheses and semi-synthetic methods. These analogs may be used as anti-microbial agents or anti-proliferative agents in the treatment of diseases of humans or other animals.
• Mechanism of Alkoxy Groups Substitution by Grignard Reagents on Aromatic Rings and Experimental Verification of Theoretical Predictions of Anomalous Reactions
  作者：Gonzalo Jiménez-Osés、Anthony J. Brockway、Jared T. Shaw、K. N. Houk

  DOI：10.1021/ja4015937

  日期：2013.5.1

  The mechanism of direct displacement of alkoxy groups in vinylogous and aromatic esters by Grignard reagents, a reaction that is not observed with expectedly better tosyloxy leaving groups, is elucidated computationally. The mechanism of this reaction has been determined to proceed through the inner-sphere attack of nucleophilic alkyl groups from magnesium to the reacting carbons via a metalaoxetane

  通过计算阐明了插烯酯和芳香酯中烷氧基被格氏试剂直接置换的机制，该反应在预期更好的甲苯磺酰氧基离去基团中未观察到。该反应的机理已确定为通过金属氧杂环丁烷过渡态从镁到反应碳的亲核烷基的内球攻击进行。与反应的烷氧基和羰基形成强镁螯合物决定了观察到的反应性和选择性。研究了酯、酮和醛取代基的影响。在某些情况下，计算预测的产物形成与之前报道的不同。这些预测随后得到了实验验证。论证了研究实际系统而不是作为计算系统的简化模型的重要性。