2,6‐dibenzylcyclohexanone | 36040-03-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,6‐dibenzylcyclohexanone
• 英文别名: 2,6-dibenzylcyclohexan-1-one；2,6-dibenzylcyclohexanone；2.6-Dibenzylcyclohexanon；2,6-dibenzyl-cyclohexanone；2,6-Dibenzyl-cyclohexanon；1,3-Dibenzyl-cyclohexanon-(2)
• CAS: 36040-03-6
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: BCGXZKQRZAYEKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6‐dibenzylcyclohexanone 在 phosphotungstic acid 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以57%的产率得到2,2'-propylene-1,1'-spirobiindane
  参考文献：
  名称：

  Synthesis of spirobiindanes via bis-cyclization reaction of the 1,5-diaryl-3-pentanones catalyzed by heteropoly acids

  摘要：

  Bis-cyclization reaction of the 1,5-diaryl-3-pentanones catalyzed by heteropoly acids (HPAs) was examined for the first time, and a series of spirobiindanes were synthesized. 1,5-Diaryl-3-pentanones were refluxed and dehydrated in toluene in the presence of 0.15 equiv of a heteropoly acid to furnish spirobiindanes in moderate to high yield. For the known 4,4'-dibromo7,7'-dimethoxy-1,1'-spirobiindane, the yield was upgraded from 66% to 80%. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.115
• 作为产物：
  描述：

  2,6-二苯亚甲基环己酮 在 乙醇 、 氢气 、 钯 作用下， 生成 2,6‐dibenzylcyclohexanone
  参考文献：
  名称：

  Borsche, Chemische Berichte, 1912, vol. 45, p. 50

  摘要：

  DOI：

文献信息

• Iron-Catalyzed Ligand Free α-Alkylation of Methylene Ketones and β-Alkylation of Secondary Alcohols Using Primary Alcohols
  作者：Anitha Alanthadka、Sourajit Bera、Debasis Banerjee

  DOI：10.1021/acs.joc.9b01600

  日期：2019.9.20

  demonstrate a general and broadly applicable catalytic cross coupling of methylene ketones and secondary alcohols with a series of primary alcohols to disubstituted branched ketones. A simple and nonprecious Fe2(CO)9 catalyst enables one-pot oxidations of both primary and secondary alcohols to a range of branched gem-bis(alkyl) ketones. A number of bond activations and formations selectively occurred in

  在本文中，我们证明了亚甲基酮和仲醇与一系列伯醇与二取代的支链酮的通用且广泛适用的催化交叉偶联。一种简单且非贵重的Fe 2（CO）9催化剂可将一元醇和仲醇一锅氧化成一系列支链宝石-双（烷基）酮。在一个罐中选择性地发生许多键的活化和形成，以提供酮产物。偶联反应可以以克为单位进行，并成功地用于合成阿兹海默氏病药物。可以实现甾体激素的烷基化。单一催化剂可以使用两种不同的醇将一锅法双烷基化为双杂芳基酮。使用IR探针，氘标记和动力学实验的初步机理研究确定了使用Fe催化剂参与借氢过程的过程，该反应产生H 2和H 2 O作为副产物。
• Alkylation of Ketones Catalyzed by Bifunctional Iron Complexes: From Mechanistic Understanding to Application
  作者：Charlotte Seck、Mbaye Diagne Mbaye、Sébastien Coufourier、Alexis Lator、Jean-François Lohier、Albert Poater、Thomas R. Ward、Sylvain Gaillard、Jean-Luc Renaud

  DOI：10.1002/cctc.201701241

  日期：2017.12.8

  Cyclopentadienone iron dicarbonyl complexes were applied in the alkylation of ketones with various aliphatic and aromatic ketones and alcohols via the borrowing hydrogen strategy in mild reaction conditions. DFT calculations and experimental works highlight the role of the transition metal Lewis pairs and the base. These iron complexes demonstrated a broad applicability in mild conditions and extended

  环戊二烯酮铁二羰基配合物通过在适当的反应条件下借用氢的策略，用于酮与各种脂族和芳族酮和醇的烷基化反应中。DFT计算和实验工作突出了过渡金属路易斯对和碱的作用。这些铁络合物在温和条件下显示出广泛的适用性，并扩展了底物的范围。
• Controlling the selectivity and efficiency of the hydrogen borrowing reaction by switching between rhodium and iridium catalysts
  作者：Danfeng Wang、Roy T. McBurney、Indrek Pernik、Barbara A. Messerle

  DOI：10.1039/c9dt02819f

  日期：——

  forming new carbon–carbon bonds. However, this transformation can result in more than one product being formed. The work reported here utilises bidentate triazole-carbene ligated iridium and rhodium complexes as catalysts for the selective formation of alkylated ketone or alcohol products. Switching from an iridium centre to a rhodium centre in the complex resulted in significant changes in product selectivity

  酮的催化烷基化与醇通过氢借用方法（HB）有可能成为形成新的碳-碳键的高效方法。但是，这种转变可能导致形成不止一种产品。此处报道的工作利用双齿三唑-卡宾连接的铱和铑配合物作为催化剂，用于选择性形成烷基化的酮或醇产物。从配合物中的铱中心转变为铑中心导致产物选择性的显着变化。还研究了其他因素（碱，碱负载，溶剂和反应温度）以进一步调节选择性。使用优化的条件来证明跨越17种酮和14种含有各种官能团的醇的反应范围。
• Triethylgallium as a Nonnucleophilic Base to Generate Enolates from Ketones
  作者：Yoshio Nishimura、Yutaka Miyake、Ryo Amemiya、Masahiko Yamaguchi

  DOI：10.1021/ol061948m

  日期：2006.10.1

  Triethylgallium deprotonated cyclic and acyclic ketones at 125-175 degrees C without forming carbonyl addition products, and the resulting gallium enolates underwent facile C-benzoylation and an aldol reaction. Unsymmetrical ketones were preferentially enolized at the methylene moiety, which was under kinetic control. [reaction: see text]

  三乙基镓在125-175℃下使环和非环酮去质子化，而没有形成羰基加成产物，并且所得的烯醇镓容易进行C-苯甲酰化和羟醛反应。不对称的酮优先在动力学控制的亚甲基部分被烯醇化。[反应：看文字]
• Piano‐stool Ru (II) arene complexes that contain ethylenediamine and application in alpha‐alkylation reaction of ketones with alcohols
  作者：Serdar Batıkan Kavukcu、Salih Günnaz、Onur Şahin、Hayati Türkmen

  DOI：10.1002/aoc.4888

  日期：2019.5

  borrowing hydrogen strategy in mild reaction conditions within a short time. The catalytic system has a broad substrate scope, which allows the synthesis of alpha alkylated ketones with excellent yields. The electronic and steric effects of complexes on catalytic activity were analysed. The influence of the carbon chain length of the ligand on the alpha‐alkylation reaction of ketones was also investigated

  制备了一系列带有乙二胺与芳基和脂肪族基团的钢琴凳Ru（II）配合物（Ru 1-7），并通过1 H，13 C，19 F和31 P NMR光谱，FT-IR和元素分析进行​​了全面表征。Ru 2–4和Ru 7的晶体结构由X射线晶体学确定。通过借用氢的策略，在短时间内温和的反应条件下，将它们成功地用于脂肪族和芳香族酮与醇的α（α）-烷基化反应。该催化体系具有广泛的底物范围，这允许以优异的产率合成α烷基化的酮。分析了配合物对催化活性的电子和空间效应。还研究了配体碳链长度对酮的α-烷基化反应的影响。还通过d 8-甲苯中的1 H-NMR光谱检查了催化循环。