phenylcycloheptane | 4401-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylcycloheptane
• CAS: 4401-18-7
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: ZQFWLIVWPCXOQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  phenylcycloheptane 在 palladium on activated charcoal 氢气 、 硝酸 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (4-aminophenyl)cycloheptane
  参考文献：
  名称：

  Synthesis and evaluation of 4-alkylanilines as mammary tumor inhibiting aromatase inhibitors

  摘要：

  The 4-alkylanilines 1-20 were synthesized to elucidate the importance of the glutarimide moiety for the aromatase inhibiting activity of aminoglutethimide [3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione, AG], the only non-steroidal aromatase inhibitor which is commercially available at present. The most interesting compounds were the (4-aminophenyl)cycloalkanes 4-6 (4, c-pentyl; 5, c-hexyl; 6, c-heptyl) and the 1-alkyl-1-(4-aminophenyl)cyclohexanes 1-3 (1, CH3; 2, C2H5; 3, n-C3H7). Derivatives 1-6 are stronger inhibitors of human placental aromatase than AG exhibiting relative potencies from 1.5 to 2.7 (AG=1). For selectivity of action, the inhibition of desmolase (cholesterol side chain cleavage enzyme) was determined. Compounds 1-3 showed an inhibition comparable to AG, whereas compounds 4-6 exhibited no effect on desmolase. Being more potent and selective aromatase inhibitors in vitro, compounds 4-6, however, were not superior to AG in vivo, when the reduction of plasma estradiol concentration and the tumor inhibiting activity (PMSG-primed SD rats and DMBA-induced mammary carcinoma of the SD rat, postmenopausal model) were concerned.

  DOI：

  10.1016/0223-5234(92)90188-7
• 作为产物：
  描述：

  环庚三烯 在 palladium on activated charcoal 氢气 作用下， 反应 2.0h， 生成 phenylcycloheptane
  参考文献：
  名称：

  The Arylation of Cycloheptatriene

  摘要：

  DOI：

  10.1021/ja01497a033

文献信息

• Benzylic Carbon Oxidation by an in situ Formed <i>o</i>-Iodoxybenzoic Acid (IBX) Derivative
  作者：Thottumkara Vinod、Lawanya Ojha、Shashi Kudugunti、Padma Maddukuri、Amitha Kommareddy、Meena Gunna、Praveen Dokuparthi、Hima Gottam、Kiran Botha、Divya Parapati

  DOI：10.1055/s-0028-1087384

  日期：——

  Benzylic C-H bonds are selectively oxidized to the corresponding carbonyl functionalities using catalytic quantities of 2-iodobenzoic acid (2IBAcid) and Oxone®. The reported procedure tolerates different functional groups and operates under mild conditions. A radical mechanism is proposed for the transformation and evidence supporting the proposed mechanism is also presented.

  使用催化量的2-碘苯甲酸（2IBAcid）和Oxone®，可以将苄基C-H键选择性地氧化为相应的羰基功能团。该方法适用于多种官能团，并在温和条件下进行。针对这一转化过程，提出了一个自由基机理，并展示了支持该机理的证据。
• General C(sp²)–C(sp³) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts
  作者：Blaise L. Truesdell、Taylor B. Hamby、Christo S. Sevov

  DOI：10.1021/jacs.0c01475

  日期：2020.3.25

  development of an electrochemical methodology for XEC that utilizes redox-active shuttles developed by the energy-storage community to protect reactive coupling catalysts from overreduction. The resulting electrocatalytic system is practical, scalable, and broadly applicable to the reductive coupling of a wide range of aryl, heteroaryl, or vinyl bromides with primary or secondary alkyl bromides. The impact

  由电化学促进的烷基和芳基卤化物的交叉亲电偶联 (XEC) 代表了需要化学计量数量的高能还原剂的传统方法的有吸引力的替代方法。最重要的是，电还原可以很容易地超过化学还原剂的还原电位，从而以改进的反应性和选择性激活催化剂，否则这些催化剂与传统还原剂不相容。这项工作详细介绍了 XEC 电化学方法的机械驱动开发，该方法利用储能社区开发的氧化还原活性穿梭机来保护反应偶联催化剂免于过度还原。所得电催化体系实用、可扩展，并广泛适用于各种芳基、杂芳基、或乙烯基溴与伯或仲烷基溴。过充电保护作为电合成方法策略的影响通过添加氧化还原梭（通常>80%）和没有添加氧化还原梭（通常<20%）的偶联反应产率的巨大差异得到强调。除了对广泛的底物具有出色的产率外，还可以在高电流和数克规模下进行防止过度还原的反应。
• Cross-coupling of alkyl halides with aryl or alkyl Grignards catalyzed by dinuclear Ni(ii) complexes containing functionalized tripodal amine-pyrazolyl ligands
  作者：Fei Xue、Jin Zhao、T. S. Andy Hor

  DOI：10.1039/c3dt32111h

  日期：——

  Structurally distinctive dinuclear Ni(II) complexes with furan or thiophene tethered amine-pyrazolyl tripodal hybrid ligands have been synthesized and crystallographically characterized. All complexes are catalytically active towards cross-coupling of aryl/alkyl Grignard reagents with β-H containing alkyl halides at room temperature in the presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA). The catalytic efficacy of the complexes is dependent on the tether substituent at the central amine. Two species, Ni(II) TMEDA and Mg(II) TMEDA complexes, have been isolated from the catalytic reaction mixtures under different conditions. Some ligand-stabilized Ni(II) and Mg(II) bimetallic species have also been identified in the ESI-MS spectra.

  具有独特结构的二核Ni(II)配合物，其配体为带有呋喃或噻吩连接的氨基-吡唑啉三脚架杂化配体，已成功合成并经晶体学表征。所有这些配合物在室温下，并在N,N,N′,N′-四甲基乙二胺（TMEDA）的存在下，对芳基/烷基格氏试剂与含β-H的烷基卤化物交叉偶联反应具有催化活性。配合物的催化效率取决于中心胺的连接基团。在不同的反应条件下，从催化反应混合物中分离出两种物质：Ni(II) TMEDA和Mg(II) TMEDA配合物。在ESI-MS谱中还鉴定出了一些配体稳定的Ni(II)和Mg(II)双金属物种。
• Recyclable cobalt(0) nanoparticle catalysts for hydrogenations
  作者：Philipp Büschelberger、Efrain Reyes-Rodriguez、Christian Schöttle、Jens Treptow、Claus Feldmann、Axel Jacobi von Wangelin、Robert Wolf

  DOI：10.1039/c8cy00595h

  日期：——

  The search for new hydrogenation catalysts that replace noble metals is largely driven by sustainability concerns and the distinct mechanistic features of 3d transition metals. Several combinations of cobalt precursors and specific ligands in the presence of reductants or under high-thermal conditions were reported to provide active hydrogenation catalysts. This study reports a new method of preparation

  寻找替代贵金属的新型加氢催化剂的主要原因是对可持续性的关注以及3d过渡金属的独特机械特性。据报道，在还原剂存在下或在高温条件下，钴前体和特定配体的几种组合可提供活性加氢催化剂。这项研究报告了一种在不存在配体或表面活性剂的情况下通过还原商业CoCl 2制备小的单分散Co（0）纳米颗粒（3-4 nm）的新方法。在烯烃，炔烃，亚胺和杂芳烃（2–20 bar H 2）的氢化中观察到高催化活性。磁性使催化剂分离和多次回收成为可能。
• Amine‐Borane Dehydrogenation and Transfer Hydrogenation Catalyzed by α‐Diimine Cobaltates
  作者：Thomas M. Maier、Sebastian Sandl、Ilya G. Shenderovich、Axel Jacobi von Wangelin、Jan J. Weigand、Robert Wolf

  DOI：10.1002/chem.201804811

  日期：2019.1.2

  catalyze the dehydrogenation of several amine‐boranes. Based on the excellent catalytic properties, an especially effective transfer hydrogenation protocol for challenging olefins, imines, and N‐heteroarenes was developed. NH3BH3 was used as a dihydrogen surrogate, which transferred up to two equivalents of H2 per NH3BH3. Detailed spectroscopic and mechanistic studies are presented, which document the rate

  阴离子α二亚胺钴络合物，例如[K（THF）1.5 （迪普边）的Co（η 4 -cod）}]（1 ;卜先生= 2,6-二异丙基，COD = 1,5-环辛二烯），催化几种胺硼烷的脱氢。基于出色的催化性能，开发了一种特别有效的转移氢化方案，用于挑战性烯烃，亚胺和N-杂芳烃。NH 3 BH 3用作二氢替代物，每个NH 3 BH 3最多可转移两个当量的H 2。。提出了详细的光谱学和机理研究，这些研究证明了胺硼烷中酸性质子的速率测定。

表征谱图