环己基(2-甲氧基苯基)甲酮 | 111504-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 环己基(2-甲氧基苯基)甲酮
• 英文名称: (E)-N′-(cyclohexyl(2-methoxyphenyl)methylene)-4-methylbenzenesulfonohydrazide
• 英文别名: cyclohexyl(2-methoxyphenyl)methanone；cyclohexyl-(2-methoxyphenyl)methanone
• CAS: 111504-19-9
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: IOVWHDLNFVGIRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  环己基(2-甲氧基苯基)甲酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 120.0h， 生成 [(2R,4R)-2-Cyclohexyl-2-(2-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-dimethyl-amine
  参考文献：
  名称：

  Angeli, Piero; Brasili, Livio; Franchini, Silvia, Medicinal Chemistry Research, 1999, vol. 9, # 2, p. 89 - 97

  摘要：

  DOI：
• 作为产物：
  描述：

  环己甲酰氯 在 盐酸 、 甲醇 、 三甲基氯硅烷 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 苄基三乙基氯化铵 、 水 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 23.33h， 生成 环己基(2-甲氧基苯基)甲酮
  参考文献：
  名称：

  通过亚胺的 Minisci 型反应将醛一锅转化为酮

  摘要：

  描述了一种通过初步形成醛亚胺将醛转化为酮的方法。亚胺参与酸促进的 Minisci 型反应，与在光氧化还原条件下由N-羟基邻苯二甲酰亚胺的酯产生的烷基自由基发生反应。添加亚胺离子后形成的氨基自由基阳离子被认为是决定反应结果的关键中间体。

  DOI：

  10.1021/acs.orglett.3c03764

文献信息

• Rapid and Direct Photocatalytic C(sp ³ )−H Acylation and Arylation in Flow
  作者：Daniele Mazzarella、Antonio Pulcinella、Loïc Bovy、Rémy Broersma、Timothy Noël

  DOI：10.1002/anie.202108987

  日期：2021.9.20

  photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)−C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced

  在此，我们报告了一种光催化程序，该程序可以使未官能化的烷基衍生物在流动中酰化/芳基化。该方法利用十钨酸盐阴离子作为氢原子提取物并产生亲核碳中心自由基的能力，这些自由基被镍催化剂拦截以最终形成 C(sp 3 )-C(sp 2 ) 键。由于流动条件的强化，反应时间可以从 12-48 小时减少到仅 5-15 分钟。最后，动力学测量强调了强化条件如何不改变反应机制，而是可靠地加速整个过程。
• Friedel–Crafts Acylation of Arenes Catalyzed by Bromopentacarbonylrhenium(I)
  作者：Hiroyuki Kusama、Koichi Narasaka

  DOI：10.1246/bcsj.68.2379

  日期：1995.8

  The intermolecular Friedel–Crafts acylation of aromatic compounds (such as toluene, m-xylene, and anisole) with various acid chlorides proceeds by using a catalytic amount of bromopentacarbonylrhen...

  芳香族化合物（如甲苯、间二甲苯和苯甲醚）与各种酰氯的分子间弗瑞德-克来福特酰化反应是通过使用催化量的溴五羰基苯...
• Synthesis of <i>Ortho</i>/<i>Ortho</i>′-Substituted 1,1-Diarylethylenes through Cross-Coupling Reactions of Sterically Encumbered Hydrazones and Aryl Halides
  作者：Maxime Roche、Abdallah Hamze、Olivier Provot、Jean-Daniel Brion、Mouad Alami

  DOI：10.1021/jo3023268

  日期：2013.1.18

  ortho/ortho′-substituents on the aromatic ring with various ortho-, meta-, and para-substituted aryl halides 3 was investigated. To accomplish successfully this challenging coupling, fine-tuning of the reaction conditions were required. The newly established PdCl2(MeCN)2/Xphos/NaO-t-Bu/F-benzene system in a sealed tube is compatible with a broad spectrum of both coupling partners, regardless of their electronic

  的空间位的反应性受阻Ñ -tosylhydrazones 2设有邻/邻'与各芳环上的-取代基的邻位- ，间位-和对位-取代的芳基卤化物3进行了研究。为了成功完成这一具有挑战性的偶联，需要对反应条件进行微调。新建立的PdCl 2（MeCN）2 / Xphos / NaO- t密封管中的-Bu / F-苯系统可与多种偶合伙伴兼容，无论它们的电子和位阻性质如何。该方案已成功应用于applied吨衍生物的合成。
• Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates
  作者：Xijing Li、Gang Zou

  DOI：10.1016/j.jorganchem.2015.07.009

  日期：2015.10

  A general and efficient acylative Suzuki coupling of active amides with diarylborinic acids has been achieved by using 1 mol% Pd(PCy3)(2)Cl-2/0.6 mol% PCy3 as catalyst system taking advantage of modifiable reactivities of acyl-nitrogen bonds of amides. Both electronic and steric influences from either aryl or acyl counterparts on the coupling proved to be negligible or small. A variety of aryl ketones including sterically hindered ones could be synthesized by the coupling of diarylborinic acids in good to excellent yields. Sodium tetraarylborates could also be used as high atom-economy aryl source in the palladium-catalyzed cross-coupling with active amides. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond
  作者：Xinying Zhang、Zhangxin Wang、Xuesen Fan、Jianji Wang

  DOI：10.1021/acs.joc.5b01824

  日期：2015.11.6

  In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp(3))-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.