ethyl 4-(naphthalen-2-yl)benzoate | 119999-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 4-(naphthalen-2-yl)benzoate
• 英文别名: 2-(4-ethoxycarbonylphenyl)naphthalene；Ethyl 4-naphthalen-2-ylbenzoate
• CAS: 119999-21-2
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: JXXJCYSQAHODTM-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  429.5±24.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  ethyl 4-(naphthalen-2-yl)benzoate 在 氢氧化钾 、 三氯化铝 作用下， 以 甲醇 、 二硫化碳 为溶剂， 反应 1.0h， 生成 4-(5,5,8,8-四甲基-6,7-二氢蒽-2-基)苯甲酸
  参考文献：
  名称：

  Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids

  摘要：

  A series of conformationally restricted analogues of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propenyl ] benzoic acid--(E)-4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2 - propenyl]benzoic acid, (E)-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-bu ten- 2-yl]benzoic acid, trans-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl) cyclopropyl]benzoic acid, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoic acid, 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid, 6-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid and 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-5-methyl-2- naphthalenecarboxylic acid--were synthesized and screened for retinoid biological activity. Comparison of the conformers of these analogues generated by molecular mechanics calculations with the biological activity profiles of these compounds indicates that geometric constraints required for high biological activity are imposed on the bridge joining the two aromatic ring systems by the retinoid receptor.

  DOI：

  10.1021/jm00127a018
• 作为产物：
  描述：

  (2-naphthyl) tert-butyl carbonate 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-bis(adamantan-2-yl)imidazolin-2-yliden chloride 、 5,5-二甲基-2-苯基-1,3,2-二氧硼杂 、 sodium ethanolate 、 sodium hydride 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 52.0h， 生成 ethyl 4-(naphthalen-2-yl)benzoate
  参考文献：
  名称：

  铑催化的氨基甲酸芳基酯与芳基硼试剂的交叉偶联

  摘要：

  已经开发出一种新方法，用于铑催化的氨基甲酸芳基酯与有机硼试剂的交叉偶联。使用带有2-金刚烷基，即I（2-Ad）的NHC配体对于反应成功是必不可少的。该反应涉及铑介导的氨基甲酸芳基酯的相对惰性的C（芳基）-O键的活化。

  DOI：

  10.1016/j.tet.2015.02.088

文献信息

• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• Use of functionalized onium salts as a soluble support for organic synthesis
  申请人：Vaultier Michel

  公开号：US20070043234A1

  公开（公告）日：2007-02-22

  The invention relates to the use of a onium salt functionalized by at least one organic function, as a soluble support, in the presence of at least one organic solvent, for organic synthesis of a molecule, in a homogenous phase, by at least one transformation of said organic function. The onium salt enables the synthesized molecule to be released. The onium salt is present in liquid or solid form at room temperature and corresponds to formula A 1 + , X 1 − , wherein A 1 + represents a cation and X 1 − represents an anion.

  该发明涉及使用至少一个有机功能官能化的离子盐作为可溶性支持体，在至少一个有机溶剂的存在下，用于在均相相中通过至少一个所述有机功能的转化对分子进行有机合成。该离子盐使合成的分子能够被释放。该离子盐在室温下以液态或固态形式存在，符合以下公式A1+，X1−，其中A1+代表阳离子，X1−代表阴离子。
• Palladium-Catalyzed Three-Component Coupling of Ynamides
  作者：Hideaki Wakamatsu、Ayano Takahashi、Ayaka Ishii、Youhei Kikuchi、Madoka Sasaki、Yukako Saito、Yoshihiro Natori、Yuichi Yoshimura

  DOI：10.1021/acs.orglett.0c01426

  日期：2020.7.17

  A palladium-catalyzed regioselective three-component coupling of ynamides was developed. The reaction proceeded smoothly to furnish the desired products when carried out at 70 °C in acetonitrile/water with potassium carbonate in the presence of 2.5 mol % Pd2(dba)3·CHCl3 without a ligand. Various iodides and boronic acids were used in this reaction, and a carbon–carbon bond was formed with satisfactory

  开发了钯催化的乙酰胺的区域选择性三组分偶联。当在没有配体的2.5mol％Pd 2（dba）3 ·CHCl 3存在下于70℃在乙腈/水中与碳酸钾一起进行时，反应平稳进行以提供所需的产物。该反应中使用了各种碘化物和硼酸，并且从酰胺中形成了具有令人满意的区域选择性的碳-碳键。
• Palladium-Catalyzed Cross-Coupling of Unactivated Aryl Sulfides with Arylzinc Reagents under Mild Conditions
  作者：Shinya Otsuka、Daishi Fujino、Kei Murakami、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/chem.201404380

  日期：2014.10.6

  Cross‐coupling of general aryl alkyl sulfides with arylzinc reagents proceeds smoothly, even at room temperature or below, with a palladium–N‐heterocyclic carbene (NHC) catalyst. When combined with reactions that are unique to organosulfurs, that is, the SNAr sulfanylation or Pummerer reaction, the cross‐coupling offers interesting transformations that are otherwise difficult to achieve. An alkylsulfanyl

  一般的芳基烷基硫化物与芳基锌试剂的交叉偶联，即使在室温或低于室温下，使用钯-N-杂环卡宾（NHC）催化剂也能顺利进行。当与有机硫特有的反应（即S N Ar磺酰化或Pummerer反应）结合使用时，交叉偶联可提供有趣的转化，而这些转化很难实现。烷基硫烷基优先被转化，而甲苯磺酰氧基和氯完好无损，这扩大了正交交叉偶联的种类。
• Single-Electron-Transfer-Induced Coupling of Arylzinc Reagents with Aryl and Alkenyl Halides
  作者：Eiji Shirakawa、Fumiko Tamakuni、Eugene Kusano、Nanase Uchiyama、Wataru Konagaya、Ryo Watabe、Tamio Hayashi

  DOI：10.1002/anie.201308200

  日期：2014.1.7

  reagents/zinc chloride, were found to undergo coupling with aryl and alkenyl halides without the aid of transition‐metal catalysis to give biaryls and styrene derivatives, respectively. In this context, we have already reported the corresponding reaction using aryl Grignard reagents instead of arylzinc reagents. Compared with the Grignard cross‐coupling, the present reaction features high functional‐group

  发现由芳基卤化物/锌粉或芳基格氏试剂/氯化锌制备的芳基锌试剂在不借助过渡金属催化的情况下与芳基和烯基卤化物偶合，分别得到联芳基和苯乙烯衍生物。在这种情况下，我们已经报道了使用芳基格氏试剂代替芳基锌试剂的相应反应。与格利雅交叉偶联相比，本反应具有较高的官能团耐受性，亲电基团（如烷氧羰基和氰基）可兼用作芳基锌试剂和芳基卤化物上的取代基。芳基卤化物接收一个电子，从而被活化为相应的阴离子基团，与芳基锌试剂反应，从而产生交叉偶联产物。