2-phenyl-7-methoxytetralone | 101596-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-7-methoxytetralone
• 英文别名: 7-methoxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one；7-Methoxy-2-phenyl-1-tetralon；7-methoxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 101596-87-6
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: UGBDVVMRGIAMHO-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C(Solv: ligroine (8032-32-4))
• 沸点：
  420.9±45.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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-phenyl-7-methoxytetralone 在 palladium on activated charcoal 叠氮磷酸二苯酯 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[(1R,2R)-7-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]-2,2-diphenylacetamide
  参考文献：
  名称：

  Inhibitors of Acyl CoA:Cholesterol Acyltransferase

  摘要：

  Conformational restriction of previously disclosed acyclic diphenylethyl)diphenylacetamides led to the discovery of several potent inhibitors of acyl CoA:cholesterol acyltransferase (ACAT). cis-[2-(4-Hydroxyphenyl)-1-indanyl]diphenylacetamide (4a) was the mo st potent ACAT inhibitor identified (IC50 = 0.04 mu M in an in vitro rat hepatic microsomal ACAT assay, ED(50) = 0.72 mg/kg/day in cholesterol-fed hamsters).

  DOI：

  10.1021/jm950833d
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 palladium diacetate 、 三正丁基甲氧基锡 、 对甲苯磺酸 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 生成 2-phenyl-7-methoxytetralone
  参考文献：
  名称：

  Inhibitors of Acyl CoA:Cholesterol Acyltransferase

  摘要：

  Conformational restriction of previously disclosed acyclic diphenylethyl)diphenylacetamides led to the discovery of several potent inhibitors of acyl CoA:cholesterol acyltransferase (ACAT). cis-[2-(4-Hydroxyphenyl)-1-indanyl]diphenylacetamide (4a) was the mo st potent ACAT inhibitor identified (IC50 = 0.04 mu M in an in vitro rat hepatic microsomal ACAT assay, ED(50) = 0.72 mg/kg/day in cholesterol-fed hamsters).

  DOI：

  10.1021/jm950833d

文献信息

• Blue Light Promoted Difluoroalkylation of Aryl Ketones: Synthesis of Quaternary Alkyl Difluorides and Tetrasubstituted Monofluoroalkenes
  作者：Kangkui Li、Jingchao Chen、Chunhui Yang、Keyang Zhang、Chunxiang Pan、Baomin Fan

  DOI：10.1021/acs.orglett.0c01294

  日期：2020.6.5

  cost-effective method for the preparation of fluoroalkylated compounds has been described by the direct photoexcitation of halofluoroalkanes with blue light absorptivity, enabling the difluoroalkylation of aryl ketones. The methodology has provided an efficient, mild, and catalyst-free synthetic method for quaternary difluoroalkylated arenes and tetrasubstituted monofluoroalkenes.

  通过直接光激发具有蓝色光吸收性的卤代氟烷烃，从而实现了芳基酮的二氟烷基化，已经描述了一种制备氟代烷基化化合物的简便且经济高效的方法。该方法为季二氟烷基化的芳烃和四取代的单氟烯烃提供了一种高效，温和且无催化剂的合成方法。
• Design and synthesis of 3-phenyltetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands. Part II
  作者：Sophie Durieux、Angéline Chanu、Christophe Bochu、Valérie Audinot、Sophie Coumailleau、Jean A. Boutin、Philippe Delagrange、Daniel H. Caignard、Caroline Bennejean、Pierre Renard、Daniel Lesieur、Pascal Berthelot、Saïd Yous

  DOI：10.1016/j.bmc.2009.03.023

  日期：2009.4

  developed new tetrahydronaphthalenic derivatives of melatonin that have been tested as selective melatonin receptors ligands. Regarding the role of the phenyl substituent to obtain selective ligands, modulation of selectivity and activity have been achieved by modifications of the acyl group and substitutions on the phenyl ring. Ten of the seventeen evaluated derivatives have MT2 receptor affinity similar

  在对褪黑素能受体进行研究之后，我们开发了褪黑素的新四氢萘衍生物，这些衍生物已作为选择性褪黑素受体配体进行了测试。关于苯基取代基获得选择性配体的作用，通过修饰酰基和苯环上的取代来实现选择性和活性的调节。在17种评估的衍生物中，有10种具有与褪黑激素相似的MT 2受体亲和力。此外，我们已经实现了超过MT 1的MT 2选择性（选择性> 100），并且能够进一步扩展四氢邻苯二甲酸系列的RSA。但是，此处提供的化合物显示出部分激动剂或拮抗剂的行为，而不是完全激动剂。
• N-heterocyclic carbene–palladium(<scp>ii</scp>)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products
  作者：Hui-Ying Yin、Xia-Li Lin、Shu-Wan Li、Li-Xiong Shao

  DOI：10.1039/c5ob01203a

  日期：——

  NHC–Pd(II)–Im complex 1 has proven to be an efficient catalyst in the reaction between tetralones 2 and aryl chlorides 3, giving the α-arylated tetralones 4 in good to high yields. In addition, if the above reaction mixture was exposed to air at room temperature for another 3 h, the normal α-arylated products 4 can be fully oxidized to 2-aryl-2′-hydroxytetralones 6 in good yields in a one-pot procedure

  NHC-Pd（II）-Im配合物1被证明是四氢萘酮2和芳基氯3之间反应的有效催化剂，使α-芳基化四氢萘酮4的产率高至高。另外，如果上述反应混合物在室温下再暴露于空气中3小时，则正常的α-芳基化产物4可以一锅法以良好的产率被完全氧化为2-芳基-2'-羟基四氢萘酮6。 。此外，如果将含有氧化产物6的反应混合物在回流下用TsOH /甲苯溶液处理19 h，则最终的芳构化产物2-芳基萘-1-醇5可以以可接受到中等的产量实现。所有反应都能耐受四氢萘酮2和芳基氯3上的各种取代基，从而为四氢萘酮的α-芳基化和产物的进一步转化提供了一种有效的方法，并且丰富了NHC-Pd（II）配合物在有机合成中的应用。 。
• A concise synthesis of 2-benzoyl-1-indanones and 1-indanones from 2-aryl-1-tetralones
  作者：Anusueya Kumari、Saurabh Kumar Singh、Raj Bahadur Singh、Sabyasachi Bhunia、Partha Ghosh

  DOI：10.1080/00397911.2020.1771370

  日期：2020.8.2

  Abstract Methyl-2-(3-oxo-3-aryl) benzoates derived from acid catalyzed air oxidative fragmentation of 2-aryl-1-tetralones were efficiently undergone intramolecular-Claisen condensation in the presence of potassium tertiary butoxide. The resulting 2-benzoyl-1-indanones formed in two-step ring contractions were further subjected to indium triflate mediated retro-Claisen condensation to get 1-indanones

  摘要 在叔丁醇钾的存在下，由 2-芳基-1-四氢萘酮的酸催化空气氧化裂解得到的 2-(3-氧代-3-芳基) 苯甲酸甲酯可以有效地进行分子内-克莱森缩合反应。在两步环收缩中形成的所得 2-苯甲酰基-1-茚满酮进一步经受三氟甲磺酸铟介导的逆克莱森缩合反应，得到 1-茚满酮。图形概要
• RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones <i>via</i> a dynamic kinetic resolution
  作者：Jingjing Li、Jianxun Ye、Jiayu Zhou、Jing Li、Delong Liu、Wanbin Zhang

  DOI：10.1039/d2cc01193j

  日期：——

  The efficient RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolution has been achieved for the synthesis of chiral tetrahydronaphthols. The mechanism study indicated that hydrogenation with H2 gas, rather than transfer hydrogenation with EtOH solvent as the hydrogen source, predominates in the reaction pathway.

  通过动态动力学拆分实现了高效的 RuPHOX-Ru 催化的 α-取代四氢萘酮的不对称氢化，用于合成手性四氢萘酚。机理研究表明，H 2气体加氢，而不是以EtOH溶剂作为氢源的转移加氢，在反应途径中占主导地位。