ethyl 4-(4-methoxybenzyl)benzoate | 67205-88-3

• 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: ethyl 4-(4-methoxybenzyl)benzoate
• 英文别名: ethyl 4-[(4-methoxyphenyl)methyl]benzoate
• CAS: 67205-88-3
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: JFRPWHSKUZXHFF-UHFFFAOYSA-N

物化性质

• 熔点：
  44-45 °C
• 沸点：
  394.7±30.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-methoxybenzyl)benzoate 在 sodium hydroxide 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-[4-(4-hydroxybenzyl)benzyl]heptane-3,5-dione
  参考文献：
  名称：

  Antiviral activity of some .beta.-diketones. 4. Benzyl diketones. In vitro activity against both RNA and DNA viruses

  摘要：

  The synthesis and in vitro antiviral evaluation of a series of substituted benzyl beta-diketones are described. The introduction of a styryl group onto the phenyl ring enhanced activity against herpesvirus type 2. The 4-methoxystyryl homologue 8 was evaluated extensively in vitro and was found to be effective against both RNA and DNA viruses. Compound 8 was evaluated in the mouse vagina against herpes simplex type 1 and produced a significant increase in survival rate as well as in survival time.

  DOI：

  10.1021/jm00207a010
• 作为产物：
  描述：

  4-(4-甲氧基苯甲酰基)苯甲腈 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 生成 ethyl 4-(4-methoxybenzyl)benzoate
  参考文献：
  名称：

  Antiviral activity of some .beta.-diketones. 4. Benzyl diketones. In vitro activity against both RNA and DNA viruses

  摘要：

  The synthesis and in vitro antiviral evaluation of a series of substituted benzyl beta-diketones are described. The introduction of a styryl group onto the phenyl ring enhanced activity against herpesvirus type 2. The 4-methoxystyryl homologue 8 was evaluated extensively in vitro and was found to be effective against both RNA and DNA viruses. Compound 8 was evaluated in the mouse vagina against herpes simplex type 1 and produced a significant increase in survival rate as well as in survival time.

  DOI：

  10.1021/jm00207a010

文献信息

• The Crocacins: Novel Natural Products as Leads for Agricultural Fungicides
  作者：Patrick J. Crowley、Paul A. Worthington、Joe Swanborough、Olivia-Anabelle Sageot、Gordon R. Munns、Ingrid M. Devillers、Christopher R.A. Godfrey、Kevin Gillen、Ian H. Aspinall、John Williams

  DOI：10.2533/000942903777678669

  日期：——

  A short route to the synthesis of analogues of the antifungal but unstable natural product crocacin D was developed. A wide range of compounds were made in which the complex side chain was replaced by simple aromatic units, and many of them showed high activity in a mitochondrial beef heart respiration assay. Some of these compounds were active against plant pathogenic fungi of agricultural importance in glasshouse tests. In order to find compounds with greater stability than the natural crocacins, the photolabile (Z)-enamide was replaced with many different moieties, but none gave rise to useful fungicidal activity.

  一种合成抗真菌但不稳定的天然产物克罗卡辛D类似物的简短路线被开发出来。制造了广泛的化合物，其中复杂的侧链被简单的芳香单元所取代，并且其中许多化合物在牛肉线粒体呼吸试验中显示出高活性。其中一些化合物在温室测试中对农业上重要的植物病原真菌具有活性。为了找到比天然克罗卡辛更稳定的化合物，光敏性的(Z)-酰胺被许多不同的基团所取代，但没有任何一种能产生有用的杀真菌活性。

• Ligand‐Facilitated Reductive Coupling of Benzyl Chlorides with Aryl Chlorides Catalyzed by Well‐Defined Heteroleptic Ni (II)‐NHC Complexes
  作者：Gusheng Lu、Ruipeng Li、Zhengwang Shen、Qinjia Wu、Hongmei Sun

  DOI：10.1002/aoc.5741

  日期：2020.9

  3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene), complex 1 exhibited superior catalytic activity in the magnesium‐mediated reductive coupling of benzyl chlorides with aryl chlorides, featuring outstanding tolerance of both coupling partners with steric demand. This study discloses a ligand‐facilitated reductive coupling of benzyl chlorides with aryl chlorides, which provides a new and practical synthetic

  新型杂合Ni（II）配合物，带有高度受阻但具有柔性的IPr *配体，Ni（IPr *）（PPh 3）Br 2（1）和Ni（IPr *）（PCy 3）Br 2（2）（IPr * = 1,3-双（2,6-双（二苯甲基）-4-甲基苯基）咪唑-2-亚基可以轻松制备，产率分别为78％和89％。两者均通过元素分析和NMR光谱进行了表征，并对1进行了X射线晶体学分析。与2及其类似物相比，其空间要求较低的IPr配体（IPr = 1,3-二（2,6-二异丙基苯基）咪唑-2-亚基）复杂1在苄基氯与芳基氯的镁介导的还原偶联中表现出卓越的催化活性，这两种偶联伙伴均具有出色的空间耐受性。这项研究揭示了苄基氯与芳基氯的配体促进还原偶联，为二芳基甲烷的合成提供了一种新的实用合成工具。
• New Preparation of Benzylic Manganese Chlorides by the Direct Insertion of Magnesium into Benzylic Chlorides in the Presence of MnCl2·2LiCl
  作者：Paul Knochel、Pauline Quinio、Andreas Benischke、Alban Moyeux、Gérard Cahiez

  DOI：10.1055/s-0034-1379944

  日期：——

  Functionalized benzylic manganese chlorides were smoothly prepared by the direct insertion of magnesium into benzylic chlorides in the presence of MnCl2·2LiCl. Reactions with acid chlorides, aldehydes, an allyl bromide, and an enone proceed without any additional transition metal.

  在MnCl2·2LiCl存在下，通过将镁直接插入苄基氯化物中，顺利地制备了官能化苄基氯化锰。与酰氯、醛、烯丙基溴和烯酮的反应无需任何额外的过渡金属即可进行。
• Direct Pd-Catalyzed Cross-Coupling of Functionalized Organoaluminum Reagents
  作者：Klaus Groll、Tobias D. Blümke、Andreas Unsinn、Diana Haas、Paul Knochel

  DOI：10.1002/anie.201205987

  日期：2012.10.29

  A handsome couple: Through the use of the simple Pd catalyst [Pd(tmpp)2Cl2] (tmpp=tris(2,4,6‐trimethoxyphenyl)phosphine) and THF/DMF as solvent, various aryl‐, heteroaryl‐, benzyl‐ and alkylaluminum reagents can be readily cross‐coupled with aryl or heteroaryl iodides, bromides, and nonaflates, and in special cases even with chlorides and triflates. This cross‐coupling tolerates free NH2 groups, aldehydes

  一对英俊的夫妇：通过使用简单的Pd催化剂[Pd（tmpp）2 Cl 2 ]（tmpp = tris（2,4,6-三甲氧基苯基）膦）和THF / DMF作为溶剂，各种芳基，杂芳基，苄基和烷基铝试剂可以很容易地与芳基或杂芳基碘化物，溴化物和壬二酸酯交叉偶联，在特殊情况下甚至与氯化物和三氟甲磺酸酯交叉偶联。这种交叉偶联可耐受游离的NH 2基团，醛，酮，酯和硝基官能团。
• Cobalt-Catalyzed Reductive Cross-Coupling Between Benzyl Chlorides and Aryl Halides
  作者：Suman Pal、Sushobhan Chowdhury、Elodie Rozwadowski、Audrey Auffrant、Corinne Gosmini

  DOI：10.1002/adsc.201600378

  日期：2016.7.28

  cobalt‐catalyzed arylation of benzyl chlorides has been developed in order to form functionalized diarylmethanes. A variety of reactive groups either on the aryl or the benzyl halide was employed. This represents the first cobalt‐catalyzed reductive cross‐coupling which does not require any ligand and pyridine. A reaction pathway is proposed involving a radical benzyl species.

  为了形成功能化的二芳基甲烷，已经开发了一种直接还原钴催化的苄基氯芳构化的新方案。使用了芳基或苄基卤上的各种反应性基团。这代表了第一个钴催化的还原交叉偶联，不需要任何配体和吡啶。提出了涉及自由基苄基物质的反应途径。