3-methyl-1-phenylhexane-1,4-dione | 121862-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-1-phenylhexane-1,4-dione
• CAS: 121862-34-8
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: CGMQQTZXSDYTNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 反应 20.0h， 生成 3-methyl-1-phenylhexane-1,4-dione
  参考文献：
  名称：

  A New Simple Synthesis of Aryl-Substituted 1,4-Diketones

  摘要：

  1,4-二酮可通过在叔丁氧基镁或二乙氨基镁溴化物的存在下，将甲基酮与α-溴酮进行醇醛缩合反应制备，随后在三乙胺的作用下，对形成的4-溴-3-羟基酮进行重排反应。

  DOI：

  10.1055/s-1996-4215

文献信息

• Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group
  作者：Naoto Esumi、Kensuke Suzuki、Yoshihiro Nishimoto、Makoto Yasuda

  DOI：10.1021/acs.orglett.6b02869

  日期：2016.11.4

  We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the α-halocarbonyls, which are usually generated in the presence

  我们报道了可见光诱导的甲硅烷基烯醇醚与α-溴羰基化合物的自由基偶联反应，得到1,4-二羰基。使用廉价的有机染料（曙红Y）作为光氧化还原催化剂可有效地促进反应。仅提供1，4-二羰基化合物，而没有生成α-卤代羰基的羰基加合物，α-卤代羰基的羰基加合物通常是在氟阴离子或路易斯酸的存在下生成的。将多种甲硅烷基烯醇醚，α-溴代酮，α-溴代酸酯和α-溴代酰胺应用于该系统以产生偶联化合物。
• Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of γ-Diketones and γ-Ketonitriles
  作者：Yi Li、Jia-Qi Shang、Xiang-Xiang Wang、Wen-Jin Xia、Tao Yang、Yangchun Xin、Ya-Min Li

  DOI：10.1021/acs.orglett.9b00520

  日期：2019.4.5

  A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)–H bond functionalization to construct new C–C bonds and C–O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to γ-diketones and γ-ketonitriles

  通过直接的C（sp 3）-H键官能化来构建新的C-C键和C-O双键的新型铜催化的炔基羧酸与酮和烷基腈的脱羧氧化烷基化反应得到了发展。这种转变的特征是广泛的官能团相容性和易于使用的试剂的使用，从而为γ-二酮和γ-酮腈提供了一种通用方法。提出了一种可能的机制。
• Pd-Catalyzed Carbonylative Conjugate Addition of Dialkylzinc Reagents to Unsaturated Carbonyls
  作者：Daniel W. Custar、Hai Le、James P. Morken

  DOI：10.1021/ol1013476

  日期：2010.9.3

  The Pd-catalyzed addition of organozinc reagents to unsaturated carbonyls in the presence of carbon monoxide provides 1,4-diketones in good yield. The reaction was studied with a number of substituted cyclic and acyclic ketones as well as α,β-unsaturated aldehydes.

  在存在一氧化碳的情况下，Pd 催化的有机锌试剂与不饱和羰基化合物的加成以良好的产率提供了 1,4-二酮。用许多取代的环状和无环酮以及 α,β-不饱和醛研究了该反应。
• 无催化剂合成1，4-二酮类化合物的方法
  申请人：重庆医科大学

  公开号：CN104844401B

  公开（公告）日：2016-08-24

  本发明提供一种无催化剂合成1，4‑二酮类化合物的方法，在碱存在下，烯醇硅醚与α‑卤代酮在多氟醇为溶剂下发生反应得到相应的1，4‑二酮化合物。本发明所述的合成1，4‑二酮类化合物的方法，原料易得，成本低廉，反应条件温和，操作简单易控，副反应较少，后处理简单，产品收率较高，溶剂可回收并循环使用，大大节约了生产成本，具有较好的环保效益和经济效益，适宜于工业化大生产。
• Synthesis of 1,4-keto esters and 1,4-diketones via palladium-catalyzed acylation of siloxycyclopropanes. Synthetic and mechanistic studies
  作者：Tsutomu Fujimura、Satoshi Aoki、Eiichi Nakamura

  DOI：10.1021/jo00008a043

  日期：1991.4

  The reaction of a variety of siloxycyclopropanes with acid chlorides in the presence of a catalytic amount of a palladium/phosphine complex gives 1,4-dicarbonyl compounds to good yield. 1-Alkoxy-1-(trialkylsiloxy)-cyclopropanes react with both aromatic and aliphatic acid chlorides in chloroform to give 1,4-keto esters. Synthesis of 1,4-diketones by the acylation of 1-alkyl- or 1-aryl-1-siloxycyclopropanes has been achieved by carrying out the reaction if HMPA under 10-20 atm of carbon monoxide. Kinetics studies and product analysis revealed the unique mechanism of this reaction, which involves rate-determining cleavage of the strained cyclopropane carbon-carbon bond with a coordinatively unsaturated acylpalladium chloride complex. Ab initio calculations of hydroxylated cyclopropane model compounds showed that the unique reactivities of the siloxycyclopropanes may be correlated with the molecular orbital properties of these compounds rather than their ground-state structural properties.