3-(bis(4-methoxyphenyl)methyl)pentane-2,4-dione | 141221-94-5

• 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: 3-(bis(4-methoxyphenyl)methyl)pentane-2,4-dione
• 英文别名: 3-[Bis(4-methoxyphenyl)methyl]pentane-2,4-dione
• CAS: 141221-94-5
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: JEBXSUMBOBZKII-UHFFFAOYSA-N

物化性质

• 沸点：
  454.7±45.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻苯二甲醚 、 3-(bis(4-methoxyphenyl)methyl)pentane-2,4-dione 在 NaHSO₄/SiO₂ 作用下， 以 氯苯 为溶剂， 反应 6.0h， 以80%的产率得到1-(4,4'-dimethoxybenzhydryl)-3,4-dimethoxybenzene
  参考文献：
  名称：

  Simple Method for sp2–sp3 and sp3–sp3 Carbon–Carbon Bond Activation in 2-Substituted 1,3-Diketones

  摘要：

  Simple and efficient methods were developed for sp(2)-sp(3) and sp(3)-sp(3) C-C bond-activation reactions of 2-substituted 1,3-diketones. 3-Substituted 3-bromopentane-2,4-diones were deacylated in the presence of an aromatic compound and a silica gel supported Bronsted acid containing sulfonic groups. The carbocation formed by cleavage of the sp(3)-sp(3) C-C bond of the dione alkylated the aromatic compound.

  DOI：

  10.1055/s-0034-1378862
• 作为产物：
  描述：

  乙酰丙酮 、 二甲氧基苯甲醇 在 iron perchlorate hexahydrate 作用下， 反应 2.0h， 以99%的产率得到3-(bis(4-methoxyphenyl)methyl)pentane-2,4-dione
  参考文献：
  名称：

  Fe（ClO 4）3 ·×H 2 O催化仲苯甲醇与不同类型亲核试剂之间的直接CC键形成反应

  摘要：

  已经描述了温和有效的Fe（ClO 4）3 ·×H 2 O催化的1,3-二羰基化合物，富电子芳烃和杂芳烃以及4-羟基香豆素与仲苄醇的直接C-C键偶联反应。富电子芳烃和杂芳烃的苄基化导致双对称三芳基甲烷的合成。本发明的方法也适用于合成一个的抗-coagulant化合物，4-羟基-3-（1,2,3,4-四氢萘-1-基）-2- ħ从市场上可买到的底物中得到-铬-2--2-酮（香豆基（B）），产率为85％。该协议的优点是范围广，条件温和，使用廉价的催化剂以及操作简便，因为水是唯一的副产品。

  DOI：

  10.1016/j.tet.2010.02.063

文献信息

• Benzylation of β-dicarbonyl compounds and 4-hydroxycoumarin using TMSOTf catalyst: a simple, mild, and efficient method
  作者：Palani Theerthagiri、Appaswami Lalitha

  DOI：10.1016/j.tetlet.2010.08.019

  日期：2010.10

  The direct benzylation of 1,3-dicarbonyl compounds and 4-hydroxycoumarin with a wide variety of benzylic alcohols was achieved using trimethylsilyl trifluoromethanesulfonate as an efficient catalyst. The reaction proceeded under very mild conditions at room temperature providing the desired products in good to excellent yields.

  使用三甲基甲硅烷基三氟甲磺酸盐作为有效催化剂，可以用多种苄醇直接进行1,3-二羰基化合物和4-羟基香豆素的苄基化反应。反应在室温下在非常温和的条件下进行，以良好至优异的产率提供了所需的产物。
• HY and Hβ Zeolites Mediated C–C Bond Formation via Addition/Substitution Reaction of 1,3-Dicarbonyl Compounds to Alcohols and Alkenes
  作者：Murali Boosa、Divya Rohini Yennamaneni、Durgaiah Chevella、Vasu Amrutham、Krishna Sai Gajula、Ramulamma Madasu、Venugopal Akula、Narender Nama

  DOI：10.1007/s10562-022-04062-8

  日期：——

  We investigated direct addition reaction of β-diketone with several alcohols and alkenes employing solid acid zeolites (HY & Hβ). The presence of acidic sites and the porous structures exhibits and influences the catalytic activity. These heterogeneous catalysts were used directly for the nucleophilic addition/substitution reactions. HY zeolite was utilized for the reaction of various aromatic alcohols

  我们使用固体酸性沸石 (HY & Hβ) 研究了 β-二酮与几种醇和烯烃的直接加成反应。酸性位点和多孔结构的存在表现出并影响催化活性。这些非均相催化剂直接用于亲核加成/取代反应。HY 沸石用于各种含有取代基的芳香醇（如给电子基团、卤素、二苯醇、炔丙醇）与乙酰丙酮的反应，并以 14-99% 的产率得到相应的产物。Hβ 沸石用于几种取代烯烃与乙酰丙酮的反应，并提供了 35% 至 98% 产率的相应产物。大规模实验 (10 mmol) 的验证为该协议增加了额外的红利。而且，. 这些沸石（HY 和 Hβ）对可回收性的效率在五个循环中得到证明。 图形概要
• Manganese(III)-mediated carbon-carbon bond formation in the reaction of xanthenes with active methylene compounds
  作者：Hiroshi Nishino、Hironori Kamachi、Harumi Baba、Kazu Kurosawa

  DOI：10.1021/jo00039a010

  日期：1992.6

  Oxidation of xanthenes with manganese(III) acetate in the presence of active methylene compounds such as 1,3-dicarbonyl compounds, malononitrile derivatives, acetone, and nitromethane selectively gives 9-substituted xanthene derivatives in good yields. A similar oxidation of thioxanthene also yields 2-(9-thioxanthenyl)-1,3-dicarbonyl compounds in 57-91% yields. The obtained 2-(9-xanthenyl)-1,3-dicarbonyl compounds are readily converted to 2-(9-xanthenylidene)-1,3-dicarbonyl derivatives using manganese(III) complexes or 2,3-dichloro-5, 6-dicyano-1,4-benzoquinone. The mechanisms for the formation of 9-substituted xanthenes are discussed on the basis of the reaction of intermediates, the electron-donating substituent effect on the xanthene ring system, effect of additives, and comparison with a reaction of radical-trapping reagents.
• Synthesis of functionalized triarylmethanes by combination of FeCl3-catalyzed benzylations of acetylacetone with [3+3] cyclocondensations
  作者：Rasheed Ahmad Khera、Ihsan Ullah、Rasheed Ahmad、Abdolmajid Riahi、Nguyen Thai Hung、Muhammad Sher、Alexander Villinger、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2010.01.022

  日期：2010.2

  Functionalized triarylmethanes are prepared in two steps by FeCl3-catalyzed benzylation of acetylacetone to give 3-(diarylmethyl)pentane-2,4-diones and subsequent formal [3+3] cyclization of the latter with 1,3-bis(trimethylsilyloxy)-1,3-dienes (C) 2010 Elsevier Ltd All rights reserved
• Synthesis of functionalized triarylmethanes based on a ‘FeCl3-catalyzed benzylation/[3+3] cyclocondensation’ strategy
  作者：Rasheed Ahmad、Abdolmajid Riahi、Peter Langer

  DOI：10.1016/j.tetlet.2009.01.079

  日期：2009.4

  Functionalized triarylmethanes are prepared in two steps by FeCl3-catalyzed benzylation of acetylacetone to give 3-(diarylmethyl)pentane-2,4-diones and subsequent formal [3+3] cyclization of the latter with 1,3-bis(trimethylsilyloxy)-1,3-dienes. (C) 2009 Elsevier Ltd. All rights reserved.