9-(4-methylbenzyl)anthracene | 1498-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(4-methylbenzyl)anthracene
• 英文别名: 9-[(4-Methylphenyl)methyl]anthracene
• CAS: 1498-79-9
• 化学式: C₂₂H₁₈
• 分子量: 282.385
• InChiKey: MUDIZVVPKDMJJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(4-methylbenzyl)anthracene 在 吡啶 、 4-二甲氨基吡啶 、 potassium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 66.0h， 生成 9-(4-methylbenzyl)-1,4-bis(4-nitrobenzoyloxy)triptycene
  参考文献：
  名称：

  The Strength of Parallel-Displaced Arene−Arene Interactions in Chloroform

  摘要：

  Triptycene-derived compounds have been prepared to serve as conformational equilibrium reporters for direct measurements of arene-arene interactions in the parallel-displaced orientation. A series of such compounds bearing arenes with different substituents were synthesized, and the ratios of the syn and anti conformers were determined by variable-temperature NMR spectroscopy. The syn conformer allows attached arenes to interact with each other while the anti conformer does not. The free energies derived from the syn/anti ratios in chloroform range from slightly positive (0.2 kcal/mol) to considerably negative (-0.98 kcal mol) values. The interactions between the arenes bearing electron-donating groups (EDG) are either negligible or slightly repulsive, while the interactions between arenes bearing electron-withdrawing groups (EWG) are attractive. Intermediate free energy values are obtained for those compounds bearing arenes with one EDG and one EWG.

  DOI：

  10.1021/jo050049t
• 作为产物：
  描述：

  (9-anthryl)-p-methylbenzyl chloride 在 sodium tetrahydroborate 、 potassium tert-butylate 作用下， 以 二乙二醇二甲醚 、 水 、 叔丁醇 为溶剂， 反应 4.5h， 生成 9-(4-methylbenzyl)anthracene
  参考文献：
  名称：

  Reactions of (9-anthryl)arylmethyl chloride and its homologs with nucleophiles under solvolytic conditions. Notable effects of reaction conditions and substituents on the reaction sites

  摘要：

  DOI：

  10.1021/ja00395a025

文献信息

• Heteroleptic Ni(II) Complexes Bearing a Bulky Yet Flexible IBiox-6 Ligand: Improved Selectivity in Cross-Electrophile Coupling of Benzyl Chlorides with Aryl Chlorides/Fluorides
  作者：Zheng-Wang Shen、Die-Die Meng、Sajid Imran、Chun-Hui Yan、Hong-Mei Sun

  DOI：10.1021/acs.organomet.0c00515

  日期：2020.10.12

  Ni(PPh3)2Br2 to give the respective heteroleptic Ni(II) complexes Ni(IBiox-6)[P(OEt)3]Br2 (1) and Ni(IBiox-6)(PPh3)Br2 (2) in yields of 60% and 71%. Their crystal structures were characterized to reveal a rare cis disposition of the IBiox-6 ligand to the phosphite ligand in 1, while 2 possessed the more common trans configuration. Both complexes catalyzed the cross-electrophile coupling of benzyl chlorides

  名为IBiox-6的双恶唑啉衍生的NHC与Ni [P（OEt）3 ] 2 Br 2和Ni（PPh 3）2 Br 2平稳反应，分别得到杂配的Ni（II）配合物Ni（IBiox-6）[ P（OEt）3 ] Br 2（1）和Ni（IBiox-6）（PPh 3）Br 2（2）的产率分别为60％和71％。它们的晶体结构进行了表征揭示一种罕见的顺式的IBiox-6配体在亚磷酸盐配体的布置1，而2所具有的较常见的反式组态。两种配合物均通过“真正的一锅法”在50°C的Mg车削条件下催化了苄基氯与芳基氯和氟化物的亲电子交联偶联，其特点是不需要温度变化或分批添加任何偶联伴侣。特别地，配合物1在催化活性和选择性之间显示出更好的平衡。研究了由1和Mg车削催化的程序范围，为合成具有高位阻和各种官能团的二芳基甲烷提供了一种高度选择性，简单和实用的方法，包括具有不对称结构的低聚二芳基甲烷。
• Restricted Rotation Involving the Tetrahedral Carbon. XXV. Barriers to Exchange between<i>dl</i>and<i>meso</i>Forms of 9-(Arylmethyl)triptycenes
  作者：Motomichi Kono、Hiroshi Kihara、Nobuo Nakamura、Fumio Suzuki、Michinori \={O}ki

  DOI：10.1246/bcsj.52.1682

  日期：1979.6

  Barriers to exchange between dl and meso forms via rotation about the C9–Csubst bond of 9-(arylmethyl)-1,4-dimethoxytriptycenes are obtained by the use of the methoxyl signals in the 1H NMR spectra. It is found that, although the population ratios are affected by the substituent in the 9 position, the enthalpy of activation for the rotation is almost invariant at ca. 10 kcal/mol.

  通过利用 1H NMR 光谱中的甲氧基信号，得出了 9-(芳基甲基)-1,4-二甲氧基三联苯通过围绕 C9-Csubst 键旋转在 dl 和 meso 形式之间进行交换的障碍。研究发现，虽然种群比率受 9 位取代基的影响，但旋转的活化焓几乎不变，约为 10 kcal/mol。10 千卡/摩尔。
• Pd-Catalyzed Cross-Coupling of <i>Sb</i>-Aryl Stibines with Halogenomethyl Arenes to Give Unsymmetirc Diarylmethanes
  作者：Dejiang Zhang、Zhi Xu、Ting Tang、Liyuan Le、Cairong Wang、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.orglett.2c00879

  日期：2022.5.6

  Herein, we describe a general method for the synthesis of unsymmetric diarylmethanes from (hetero)aryl methyl halides and Sb-aryl stibines. This protocol shows a broad substrate scope and a good functional group tolerance. Drug molecules, including beclobrate 3al and bifemelane 3as, and drug derivatives, including celecoxib 3p, ibuprofen 3ao, and probenecid 3ap, were efficiently synthesized on a gram

  在此，我们描述了一种由（杂）芳基甲基卤化物和Sb-芳基锑合成不对称二芳基甲烷的通用方法。该协议显示了广泛的底物范围和良好的功能组耐受性。药物分子，包括 beclobrate 3al和bifemelane 3as，以及药物衍生物，包括 celecoxib 3p、布洛芬3ao和丙磺舒3ap，以克级高效合成。在对照实验结果的基础上提出了可能的机理。
• Protonation and alkylation of ambident (9-anthryl)arylmethyl anions
  作者：Masato Takagi、Masatomo Nojima、Shigekazu Kusabayashi

  DOI：10.1021/ja00352a025

  日期：1983.7
• 1,3-Dicyclohexylimidazol-2-ylidene as a Superior Ligand for the Nickel-Catalyzed Cross-Couplings of Aryl and Benzyl Methyl Ethers with Organoboron Reagents
  作者：Mamoru Tobisu、Ayaka Yasutome、Hirotaka Kinuta、Keisuke Nakamura、Naoto Chatani

  DOI：10.1021/ol502583h

  日期：2014.11.7

  A new catalytic system has been developed involving the use of Ni(cod)2 in conjunction with 1,3-dicyclohexylimidazol-2-ylidene for the cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. This method not only allows for the use of readily available methyl ethers as halide surrogates but also provides a functional group tolerant method for the late-stage derivatization of complex molecules.