1-(4-methoxyphenyl)undecan-1-one | 69657-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methoxyphenyl)undecan-1-one
• 英文别名: 1-(4-Methoxyphenyl)-1-undecanone
• CAS: 69657-36-9
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: VXTXWJDHMFLOGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  正癸烯 在 [Pd(IPr)(cin)Cl] 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 1-(4-methoxyphenyl)undecan-1-one
  参考文献：
  名称：

  钯/ NHC（NHC = N-杂环碳烯）-通过选择性N-C键断裂催化的酰胺的B-烷基铃木交叉偶联

  摘要：

  据报道，通过N-C（O）裂解，钯-NHC（NHC = N-杂环卡宾）具有高度化学选择性，催化B-sp 3-烷基试剂与活化酰胺之间的直接交叉偶联。钯-NHC预催化剂可促进酰胺的化学选择性烷基化，这是通过使用强有机金属试剂无法实现的。各种酰胺，包括直接和位点选择性的N，N -di-Boc活化后具有挑战性的伯酰胺，都与此方法兼容。顺序C（sp 2）–C（sp 2）/ C（sp 2）–C（sp 3）证明了这种温和协议的潜力）交叉偶联，该偶联使用源自共同伯酰胺键的di-Boc酰胺。该方法在B-烷基-Suzuki交叉偶联中提供了空气和水分稳定，轮廓分明且高反应性的Pd-NHC预催化剂的罕见实例。

  DOI：

  10.1021/acs.orglett.8b02911

文献信息

• Esters as Acylating Reagent in a Friedel−Crafts Reaction: Indium Tribromide Catalyzed Acylation of Arenes Using Dimethylchlorosilane
  作者：Yoshihiro Nishimoto、Srinivasarao Arulananda Babu、Makoto Yasuda、Akio Baba

  DOI：10.1021/jo801914x

  日期：2008.12.5

  The Friedel-Crafts acylation of arenes with esters by dimethylchlorosilane and 10 mol % of indium tribromide has been achieved. The key intermediate RCOOSi(Cl)Me(2) is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful. In addition, we demonstrated the direct synthesis

  已经通过二甲基氯硅烷和10mol％的三溴化铟实现了芳烃与酯的弗瑞德-克来福特酰化。关键中间体RCOOSi（Cl）Me（2）由烷氧基酯生成，并伴随有相应的烷烃生成。烷氧基酯部分的范围很广：叔丁基酯，苄基酯，烯丙基酯和异丙酯是成功的。此外，我们证明了由酯10直接合成丹参戊醇的茚满酮中间体11。
• Solvent-free chelation-assisted hydroacylation of olefin by rhodium(I) catalyst under microwave irradiation
  作者：André Loupy、Saber Chatti、Sarah Delamare、Dae-Yon Lee、Jong-Hwa Chung、Chul-Ho Jun

  DOI：10.1039/b200442a

  日期：2002.5.10

  A solvent-free protocol for the rhodium(I)-catalyzed intermolecular hydroacylation was achieved under microwave irradiation to furnish various ketones in high yields. The reactivity was improved by the addition of aniline as well as 2-amino-3-picoline and benzoic acid to induce a transimination, which facilitates the formation of intermediate aldimine. A comparison of the reactivity between the reaction performed under the conventional heating mode and the microwave irradiation using monomode reactor revealed an important specific microwave effect during the chelation-assisted hydroacylation. It is supposed that the observed specific microwave effect mainly originates from the formation of aldimine by condensation of aldehyde and amine, which leads to a development of charges in the transition state. This result confirms that the rate-determining step of the reaction is the initial condensation step rather than the subsequent hydroiminoacylation step.

  在无溶剂条件下，通过微波照射实现了铑(I)催化剂催化的分子间氢酰化反应，高效制备了多种酮类化合物。通过添加苯胺、2-氨基-3-吡啶以及苯甲酸引发转亚胺化作用，促进了中间体醛亚胺的形成，从而提高了反应活性。与传统加热方式相比，使用单模微波反应器进行氢酰化反应的活性比较揭示了螯合辅助氢酰化过程中重要的特定微波效应。据推测，所观察到的特定微波效应主要源于醛和胺缩合形成醛亚胺，导致过渡态中电荷的发展。这一结果证实了反应的速率决定步骤是初始的缩合步骤，而非随后的氢亚胺化步骤。
• Rhodium-Catalyzed Remote Isomerization of Alkenyl Alcohols to Ketones
  作者：Wenke Dong、Hongxuan Yang、Wen Yang、Wanxiang Zhao

  DOI：10.1021/acs.orglett.9b04508

  日期：2020.2.21

  We develop herein an efficient rhodium-catalyzed remote isomerization of aromatic and aliphatic alkenyl alcohols into ketones. This catalytic process, with a commercially available catalyst and ligand ([RhCl(cod)]2 and Xantphos), features high efficiency, low catalyst loading, good functional group tolerance, a broad substrate scope, and no (sub)stoichiometric additive. Preliminary mechanistic studies

  我们在本文中开发了一种有效的铑催化的芳族和脂族烯基醇远程异构化成酮的方法。该催化过程使用市售的催化剂和配体（[RhCl（cod）] 2和Xantphos），具有效率高，催化剂用量低，官能团耐受性好，底物范围宽和无（亚）化学计量添加剂的特点。初步的机理研究表明，这种转变涉及迭代解离的β-氢化物消除-迁移插入过程。
• Majima; Nagaoka; Keisuke, Chemische Berichte, 1922, vol. 55, p. 216
  作者：Majima、Nagaoka、Keisuke

  DOI：——

  日期：——
• In(III)-Mediated Chemoselective Dehydrogenative Interaction of ClMe₂SiH with Carboxylic Acids:  Direct Chemo- and Regioselective Friedel−Crafts Acylation of Aromatic Ethers
  作者：Srinivasarao Arulananda Babu、Makoto Yasuda、Akio Baba

  DOI：10.1021/ol062723e

  日期：2007.2.1

  Chemoselective dehydrogenative interaction of ClMe2SiH with a carboxylic acid group in the presence of InX3 is reported. C-13 NMR investigation revealed the formation of PhCOOSi(Cl)Me-2 as the major transient intermediate. Chemo- and regioselective Friedel-Crafts acylation of aromatic ethers directly from carboxylic acids was established.