3-(bis(4-chlorophenyl)methyl)pentane-2,4-dione | 665002-69-7

• 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: 3-(bis(4-chlorophenyl)methyl)pentane-2,4-dione
• 英文别名: 3-[Bis(4-chlorophenyl)methyl]-2,4-pentanedione；3-[bis(4-chlorophenyl)methyl]pentane-2,4-dione
• CAS: 665002-69-7
• 化学式: C₁₈H₁₆Cl₂O₂
• 分子量: 335.23
• InChiKey: KKDLKXBROGXKED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(bis(4-chlorophenyl)methyl)pentane-2,4-dione 、 邻苯二甲醚 在 NaHSO₄/SiO₂ 作用下， 以 氯苯 为溶剂， 反应 6.0h， 以96%的产率得到1-(4,4'-dichlorobenzhydryl)-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：

  4,4'-二氯二苯甲酮 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 反应 3.0h， 生成 3-(bis(4-chlorophenyl)methyl)pentane-2,4-dione
  参考文献：
  名称：

  布朗斯台德酸催化的1,3-二羰基衍生物的苄基化作用。

  摘要：

  已表明，通过简单的布朗斯台德酸（例如三氟甲磺酸（TfOH）和对甲苯磺酸（PTS））可以有效地催化1,3-二羰基化合物与苄醇的直接烷基化反应，从而以高收率产生单烷基化二羰基衍生物。在不存在亲核试剂的情况下，获得了通过正式的二聚反应生成的取代的烯烃。反应是在空气中使用未干燥的溶剂进行的，而水是该方法的唯一副产物。

  DOI：

  10.1021/ol070624a

文献信息

• Fe(ClO4)3·×H2O-Catalyzed direct C–C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles
  作者：Ponnaboina Thirupathi、Sung Soo Kim

  DOI：10.1016/j.tet.2010.02.063

  日期：2010.4

  mild and efficient Fe(ClO4)3·×H2O-catalyzed direct C–C bond coupling reactions of 1,3-dicarbonyl compounds, electron-rich arenes and heteroarenes and 4-hydroxycoumarin with secondary benzylic alcohols have been described. The benzylation of electron-rich arenes and heteroarenes leads to the synthesis of bis-symmetrical triarylmethanes. The present method is also applied to synthesis of an anti-coagulant

  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。
• Synthesis and structure of an air-stable bis(isopropylcyclopentadienyl) zirconium perfluorooctanesulfonate and its catalyzed benzylation of 1,3-dicarbonyl derivatives with alcohols
  作者：Xiaohong Zhang、Renhua Qiu、Congcong Zhou、Jingxing Yu、Ningbo Li、Shuangfeng Yin、Xinhua Xu

  DOI：10.1016/j.tet.2014.12.101

  日期：2015.2

  An air-stable uninuclear complex of bis(isopropylcyclopentadienyl) zirconium perfluorooctane sulfonate (1a center dot H2O center dot 3THF) was successfully synthesized by the reaction of (i-PrCp)(2)ZrCl2 with C17SO3Ag. The compound 1a center dot H2O center dot 3THF was characterized by different techniques (such as X-ray single crystal diffraction, TG-DSC, conductivity measurement and acid strength) and found to have the similar nature of water tolerance, air-stability, thermally-stability and strong Lewis-acidity with that of our previously reported binuclear and uninuclear zirconocenes perfluorooctanesulfonate. This novel complex was confirmed to be an effective catalyst with good recyclability and reusability for the direct benzylation of 1,3-dicarbonyl derivatives using alcohols as alkylating agents. Various 1,3-dicarbonyl and alcohols derivatives can participate in the reaction, affording the corresponding monobenzylated products in competitive yields as compared to its counterparts, such as Cp2Zr(OSO17)(2)center dot 3H(2)O center dot THF and the traditional Lewis-acid catalysts. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.
• Brønsted Acid-Catalyzed Benzylation of 1,3-Dicarbonyl Derivatives
  作者：Roberto Sanz、Delia Miguel、Alberto Martínez、Julia M. Álvarez-Gutiérrez、Félix Rodríguez

  DOI：10.1021/ol070624a

  日期：2007.5.1

  The direct alkylation of 1,3-dicarbonyl compounds with benzylic alcohols is shown to be efficiently catalyzed by simple Bronsted acids such as triflic acid (TfOH) and p-toluenesulfonic acid (PTS) to give rise to monoalkylated dicarbonyl derivatives in high yields. In the absence of the nucleophile, substituted alkenes, generated through a formal dimerization reaction, are obtained. The reactions are

  已表明，通过简单的布朗斯台德酸（例如三氟甲磺酸（TfOH）和对甲苯磺酸（PTS））可以有效地催化1,3-二羰基化合物与苄醇的直接烷基化反应，从而以高收率产生单烷基化二羰基衍生物。在不存在亲核试剂的情况下，获得了通过正式的二聚反应生成的取代的烯烃。反应是在空气中使用未干燥的溶剂进行的，而水是该方法的唯一副产物。