2-氯-1-(6-甲氧基萘-2-基)乙酮 | 93617-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氯-1-(6-甲氧基萘-2-基)乙酮
• 英文名称: 2-chloro-1-(6-methoxynaphthalen-2-yl)ethanone
• CAS: 93617-05-1
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: KKZWRHDZLNEUSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 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-氯-1-(6-甲氧基萘-2-基)乙酮 在 甲醇 、 ethyl O-(methanesulfonyl)acetohydroxamate 、 对甲苯磺酸 作用下， 以84%的产率得到6-甲氧基-2-氨基萘
  参考文献：
  名称：

  乙酰键芳烃和烷烃的脱乙酰氨基化与C–C键裂解

  摘要：

  描述了由Brønsted酸催化的C–C键断裂，由乙酰基芳烃和烷烃合成伯胺。尽管从乙酰基向胺的转化传统上需要多个步骤，但是本文所述的使用肟试剂作为氨基源的方法直接通过多米诺转肟化/贝克曼重排/品纳反应实现了转化。该方法还适用于γ-氨基丁酸的合成，如巴克洛芬和咯利普兰。

  DOI：

  10.1021/acs.orglett.9b00807
• 作为产物：
  描述：

  2-萘甲醚 、 氯乙酰氯 在 三氯化铝 作用下， 以 硝基苯 为溶剂， 反应 2.33h， 以21%的产率得到2-氯-1-(6-甲氧基萘-2-基)乙酮
  参考文献：
  名称：

  Synthesis and Photophysical and Cation-Binding Properties of Mono- and Tetranaphthylcalix[4]arenes as Highly Sensitive and Selective Fluorescent Sensors for Sodium

  摘要：

  The syntheses and properties of two calixarene-based fluorescent molecular sensors are reported. These comprise tert-butylcalix[4]arene either with one appended fluorophore and three ester groups (Calix-AMN1), or with four appended fluorophores (Calix-AMN4). The fluorophore is 6-acyl-2-methoxy-naphthalene (AMN), which contains an electron-donating substituent (methoxy group) conjugated to an electron-withdrawing substituent (carbonyl group); this allows photoinduced charge transfer (PCT) to occur upon excitation. The investigated fluoroionophores thus belong to the family of PCT fluorescent molecular sensors. In addition to the expected red shifts of the absorption and emission spectra upon cation binding, a drastic enhancement of the fluorescence quantum yield-in an "off-on" fashion comparable to that seen in photoinduced electron transfer (PET) molecular sensors-was observed. For Calix-AMN1, it increases from 10(-3) for the free ligand to 0.68 for the complex with Ca2+. This exceptional behaviour can be interpreted in terms of the relative locations of the n pi* and pi pi* levels, which depend on the charge density of the bound cation. For Calix-AMN4, in addition to the photophysical effects observed for Calix-AMN1, interactions between the chromophores by complexation with some cations have been found in the ground state (hypochromic effect) and in the excited state (excimer formation). Steady-state fluorescence anisotropy measurements for the system Na+ subset of Calix-AMN4, show a depolarization effect due to energy transfer (homotransfer) between the fluorophores. Regarding the complexing properties, a high selectivity for Na+ over K+, Li+, Ca2+ and Mg2+ was observed in ethanol and ethanol-water mixtures. The selectivity (Na+/other cations) expressed as the ratio of the stability constants was found to be more than 400.

  DOI：

  10.1002/1521-3765(20011105)7:21<4590::aid-chem4590>3.0.co;2-a

文献信息

• Solvent-free microwave-assisted multi-component reaction for preparation of 2-amino-1-aryl-2-(cyclohex-1-enyl)ethanones as precursors of pseudoephedrine analogues
  作者：Li-Jian Ma、Tsutomu Inokuchi

  DOI：10.1039/c0cc00859a

  日期：——

  Microwave irradiation of chloroacetylarenes and enamines induced an aza-Darzens reaction followed by rearrangement of the aziridinium intermediate to give (2-amino-3-alkenoyl)arenes that were reduced selectively to syn-β-aminoalcohols as pseudo-ephedrine analogues.

  氯代乙酰苯与烯胺类的微波辐射诱导了氮杂Darzens反应，接着氮杂环丙鎓中间体的重排，得到了二氧化氨基-三碳烯酰苯类化合物，这类化合物被选择性地还原为伪麻黄碱的伪手性β-氨基醇类似物。
• Deacetylative Amination of Acetyl Arenes and Alkanes with C–C Bond Cleavage
  作者：Kengo Hyodo、Genna Hasegawa、Hiroya Maki、Kingo Uchida

  DOI：10.1021/acs.orglett.9b00807

  日期：2019.4.19

  The Brønsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C–C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction

  描述了由Brønsted酸催化的C–C键断裂，由乙酰基芳烃和烷烃合成伯胺。尽管从乙酰基向胺的转化传统上需要多个步骤，但是本文所述的使用肟试剂作为氨基源的方法直接通过多米诺转肟化/贝克曼重排/品纳反应实现了转化。该方法还适用于γ-氨基丁酸的合成，如巴克洛芬和咯利普兰。
• Synthesis and Photophysical and Cation-Binding Properties of Mono- and Tetranaphthylcalix[4]arenes as Highly Sensitive and Selective Fluorescent Sensors for Sodium
  作者：Isabelle Leray、Jean-Pierre Lefevre、Jean-François Delouis、Jacques Delaire、Bernard Valeur

  DOI：10.1002/1521-3765(20011105)7:21<4590::aid-chem4590>3.0.co;2-a

  日期：2001.11.5

  The syntheses and properties of two calixarene-based fluorescent molecular sensors are reported. These comprise tert-butylcalix[4]arene either with one appended fluorophore and three ester groups (Calix-AMN1), or with four appended fluorophores (Calix-AMN4). The fluorophore is 6-acyl-2-methoxy-naphthalene (AMN), which contains an electron-donating substituent (methoxy group) conjugated to an electron-withdrawing substituent (carbonyl group); this allows photoinduced charge transfer (PCT) to occur upon excitation. The investigated fluoroionophores thus belong to the family of PCT fluorescent molecular sensors. In addition to the expected red shifts of the absorption and emission spectra upon cation binding, a drastic enhancement of the fluorescence quantum yield-in an "off-on" fashion comparable to that seen in photoinduced electron transfer (PET) molecular sensors-was observed. For Calix-AMN1, it increases from 10(-3) for the free ligand to 0.68 for the complex with Ca2+. This exceptional behaviour can be interpreted in terms of the relative locations of the n pi* and pi pi* levels, which depend on the charge density of the bound cation. For Calix-AMN4, in addition to the photophysical effects observed for Calix-AMN1, interactions between the chromophores by complexation with some cations have been found in the ground state (hypochromic effect) and in the excited state (excimer formation). Steady-state fluorescence anisotropy measurements for the system Na+ subset of Calix-AMN4, show a depolarization effect due to energy transfer (homotransfer) between the fluorophores. Regarding the complexing properties, a high selectivity for Na+ over K+, Li+, Ca2+ and Mg2+ was observed in ethanol and ethanol-water mixtures. The selectivity (Na+/other cations) expressed as the ratio of the stability constants was found to be more than 400.