2-fluoro-7-methoxy-3,4-dihydronaphthalen-1(2H)-one | 295779-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-fluoro-7-methoxy-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 2-Fluoro-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-one；2-fluoro-7-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 295779-87-2
• 化学式: C₁₁H₁₁FO₂
• 分子量: 194.206
• InChiKey: HEZRTKVDGFFSFV-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  310.2±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-fluoro-7-methoxy-3,4-dihydronaphthalen-1(2H)-one 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 12.0h， 生成 3-fluoro-6-methoxy-1,2-dihydronaphthalene
  参考文献：
  名称：

  Deleterious effect of 7-methyl group on glycosylation of 2-naphthols

  摘要：

  C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (I). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-naphthol (6) embodying the target are ineffective under different Lewis acidic conditions. The inefficiency of the glycosylation of 6 has been attributed to the steric effect exerted by C7 methyl group, which was corroborated by glycosylation studies of different 2-naphthols. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.045
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 Selectfluor 作用下， 以 甲醇 为溶剂， 生成 2-fluoro-7-methoxy-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  光诱导环己酮单加氧酶的混杂对映选择性合成 α-氟代酮

  摘要：

  报道了环己酮单加氧酶 (CHMO) 的光诱导还原脱卤混杂与 ET/PT 的新机制不同于天然还原酶的光诱导混杂。在合理设计的 CHMO 突变体催化的过程中，通过 α,α-卤代氟酮的光诱导还原脱卤合成了各种高度对映体富集的 α-氟酮。

  DOI：

  10.1002/anie.202211199

文献信息

• Solvent directing immediate fluorination of aromatic ketones using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
  作者：Stojan Stavber、Marjan Jereb、Marko Zupan

  DOI：10.1039/b003488f

  日期：——

  Reactions of aryl alkyl ketones with 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (AccufluorTM NFTh) in methanol result in selective and almost quantitative formation of the corresponding α-fluoroketones, while in acetonitrile exclusive fluorofunctionalisation of the activated aromatic ring take place.

  芳基烷基酮与 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (AccufluorTM NFTh) 在甲醇中的反应导致选择性和几乎定量地形成相应的 α-氟酮，而在乙腈中，活化的芳环发生排他性的氟官能化。
• Synthesis of new α-Aryl-α-tetralones and α-Fluoro-α-aryl-α-tetralones, preliminary antiproliferative evaluation on drug resistant cell lines and in silico prediction of ADMETox properties
  作者：Luana G. de Souza、Eduardo J. Salustiano、Kelli M. da Costa、Angela T. Costa、Vivian M. Rumjanek、Jorge L.O. Domingos、Magdalena N. Rennó、Paulo R.R. Costa

  DOI：10.1016/j.bioorg.2021.104790

  日期：2021.5

  in moderate to good yields. These compounds were evaluated for their in vitro anti-proliferative effects against human breast cancer and leukemia cell lines with diverse profiles of drug resistance. The most promising compounds, 3b, 3c, 8a and 8c, were effective on both neoplastic models. 3b and 8a induced higher toxicity on multidrug resistant cells and were able to avoid efflux by ABCB1 and ABCC1

  α-芳基-α-四氢萘酮和α-氟-α-芳基-α-四氢萘酮衍生物是通过钯催化的α-四氢萘酮和α-氟-α-四氢萘酮的α-芳基化反应合成的，溴芳烃的收率中等至良好。评估了这些化合物对具有多种耐药性的人乳腺癌和白血病细胞系的体外抗增殖作用。最有希望的化合物3b、3c、8a和8c对两种肿瘤模型均有效。3b和8a对多重耐药细胞诱导更高的毒性，并且能够避免 ABCB1 和 ABCC1 转运蛋白的外流。用于预测 ADMETox 特性的物理化学描述符的理论计算对于 Lipinski 的五法则是有利的，结果反映了对非肿瘤细胞的低影响。因此，这些化合物在开发治疗难治性癌症的药物方面显示出巨大的潜力。
• Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates
  作者：Étienne Bélanger、Clément Houzé、Nicolas Guimond、Katy Cantin、Jean-François Paquin

  DOI：10.1039/b803097a

  日期：——

  The enantioselective Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates is presented; a key feature of this transformation is the important effect of the ligand-to-palladium ratio on the enantioselectivity of the α-fluoroketones, since using a ligand excess (L/Pd ratio = 1.25 : 1) led to moderate results (30–76% ee), while using a L/Pd ratio <1 : 1.67 (to as low as 1 : 4) allowed the desired products to be obtained with high enantiopurity (up to 94% ee).

  介绍了 Pd 催化的氟化烯丙基烯醇碳酸酯的对映体选择性烯丙基化反应；这一转化的一个关键特征是配体与钯的比率对 α-氟酮的对映体选择性的重要影响，因为使用配体过量（L/Pd 比率 = 1.25 : 1）会导致中等结果（30-76% ee），而使用 L/Pd 比 <1 : 1.67（低至 1 : 4）则可获得高对映体纯度（高达 94% ee）的所需产物。
• Asymmetric Synthesis of Monofluorinated Carbocyclic Alcohols and Vicinal Difluorinated Heterocycles and Carbocycles
  作者：Lucas Bacheley、Ricardo Molina Betancourt、Rathies Ravindra、Gérard Guillamot、Phannarath Phansavath、Virginie Ratovelomanana‐Vidal

  DOI：10.1002/ejoc.202300383

  日期：2023.7.3

  A straightforward access to novel families of enantioenriched cis-monofluorinated carbocyclic alcohols has been developed through ruthenium-catalyzed asymmetric transfer hydrogenation/dynamic kinetic resolution that proceeded in high diastereo- and enantioselectivities. Valuable enantioenriched vicinal difluorinated heterocycles and carbocycles, such as trans-difluorinated indans, tetrahydronaphthalenes

  通过钌催化的不对称转移氢化/动态动力学拆分，以高非对映和对映选择性进行，开发了一种直接获得对映体富集的顺式一氟化碳环醇的新家族的方法。有价值的对映体富集的邻位二氟化杂环和碳环，例如反式二氟化茚满、四氢萘、四氢喹啉和苯并二氢吡喃也已通过相应顺式氟醇的脱氧氟化来合成。