1-phenyl-3-(2,4,6-trimethylphenyl)-1,3-propanedione | 6477-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-phenyl-3-(2,4,6-trimethylphenyl)-1,3-propanedione
• 英文别名: Mesitoylbenzoylmethan；1-mesityl-3-phenyl-propane-1,3-dione；1-Mesityl-3-phenyl-propan-1,3-dion；1-Phenyl-3-(2.4.6-trimethyl-phenyl)-propandion-(1.3)；1,3-Propanedione, 1-phenyl-3-(2,4,6-trimethylphenyl)-；1-phenyl-3-(2,4,6-trimethylphenyl)propane-1,3-dione
• CAS: 6477-28-7
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: QMZQPUAFYSEKKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 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：

  1-phenyl-3-(2,4,6-trimethylphenyl)-1,3-propanedione 在 1,4-二氧六环 、 selenium(IV) oxide 作用下， 生成 mesityl-phenyl-propanetrione
  参考文献：
  名称：

  A New Synthesis of Benzoins. 2',4',6'-Trimethylbenzoin

  摘要：

  DOI：

  10.1021/ja01313a015
• 作为产物：
  描述：

  2′,4′,6′-三甲基苯乙酮 在 乙醚 、 乙基溴化镁 作用下， 生成 1-phenyl-3-(2,4,6-trimethylphenyl)-1,3-propanedione
  参考文献：
  名称：

  Reactions of Bromomagnesium Enolates of Mesityl Ketones. II. Condensation

  摘要：

  DOI：

  10.1021/ja01878a028

文献信息

• Synthesis of Dibenzoylmethane Derivaives and Inhibition of Mutagenicity in Salmonella typhimurium.
  作者：Tominari CHOSHI、Shigenori HORIMOTO、Ching Y. WANG、Hisamitsu NAGASE、Masataka ICHIKAWA、Eiichi SUGINO、Satoshi HIBINO

  DOI：10.1248/cpb.40.1047

  日期：——

  Twenty dibenzoylmethanes with methyl, methoxy, bromo, chloro, or fluoro substitution on either one or both benzene rings were synthesized and assayed for inhibition of the mutagenicity of 2-nitrofluorene in S. typhimurium TA98. 2, 2-Dimethoxy, 3, 3-dimethoxy and 3, 3, 4, 4-tetramethoxydibenzoylmethane was as active as dibenzoylmethane. None of the halogen-substituted dibenzoylmethanes were active. These results demonstrate that dibenzoylmethanes can inhibit the mutagenicity of 2-nitrofluorene, and that modifications made on the benzene rings of dibenzoylmethane cannot enhance the antimutagencity of this parent compound.

  合成了20种二苯甲酰甲烷，它们在一个或两个苯环上分别带有甲基、甲氧基、溴、氯或氟取代基，并测定了它们对S. typhimurium TA98株2-硝基芴致突变性的抑制作用。2,2-二甲氧基、3,3-二甲氧基和3,3,4,4-四甲氧基二苯甲酰甲烷与二苯甲酰甲烷同样有效。所有含卤素取代的二苯甲酰甲烷均无效。这些结果表明二苯甲酰甲烷能抑制2-硝基芴的致突变性，在二苯甲酰甲烷的苯环上作修饰并不能增强其母体化合物的抗致突变性。
• Direct and highly regioselective and enantioselective allylation of β-diketones
  作者：Wesley A. Chalifoux、Samuel K. Reznik、James L. Leighton

  DOI：10.1038/nature11189

  日期：2012.7

  A simple, regioselective and enantioselective method for allylating β-diketones has been developed, significantly expanding the pool of easily accessible enantiomerically enriched and functionally complex tertiary carbinols. The enantioselective allylation of ketones represents a problem of fundamental importance in asymmetric reaction design, especially given that only a very small number of methods can generate tertiary carbinols. In this manuscript, the authors describe a simple, regioselective and enantioselective method for allylating β-diketones. This reaction significantly expands the pool of enantiomerically enriched and functionally complex tertiary carbinols that can be easily accessed and also overturns more than a century of received wisdom regarding the reactivity of β-diketones. The enantioselective allylation of ketones is a problem of fundamental importance in asymmetric reaction design, especially given that only a very small number of methods can generate tertiary carbinols. Despite the vast amount of attention that synthetic chemists have given to this problem1,2,3,4,5,6,7,8, success has generally been limited to just a few simple ketone types. A method for the selective allylation of functionally complex ketones would greatly increase the utility of ketone allylation methods in the chemical synthesis of important targets. Here we describe the operationally simple, direct, regioselective and enantioselective allylation of β-diketones. The strong tendency of β-diketones to act as nucleophilic species was overcome by using their enol form to provide the necessary Brønsted-acid activation. This reaction significantly expands the pool of enantiomerically enriched and functionally complex tertiary carbinols that may be easily accessed. It also overturns more than a century of received wisdom regarding the reactivity of β-diketones.

  一种简单的、区域选择性和对映选择性的烯丙基化β-二酮方法已被开发出来，显着扩大了易于获得的对映体丰富且功能复杂的叔醇的库。酮的对映选择性烯丙基化是不对称反应设计中的一个非常重要的问题，特别是考虑到只有极少数的方法可以生成叔醇。在这篇手稿中，作者描述了一种简单的区域选择性和对映选择性烯丙基化 β-二酮的方法。该反应显着扩大了对映异构体丰富且功能复杂的叔醇库，这些叔醇可以很容易地获得，并且还颠覆了一个多世纪以来关于β-二酮反应性的公认观点。酮的对映选择性烯丙基化是不对称反应设计中一个非常重要的问题，特别是考虑到只有极少数的方法可以生成叔醇。尽管合成化学家对这个问题给予了大量的关注1,2,3,4,5,6,7,8，但成功通常仅限于几种简单的酮类型。功能复杂酮的选择性烯丙基化方法将大大增加酮烯丙基化方法在重要靶标化学合成中的效用。在这里，我们描述了操作简单、直接、区域选择性和对映选择性的β-二酮烯丙基化。通过使用烯醇形式提供必要的布朗斯台德酸活化，克服了β-二酮作为亲核物质的强烈倾向。该反应显着扩大了对映体富集且功能复杂的叔醇库，并且可以很容易地获得。它还颠覆了一个多世纪以来关于β-二酮反应性的公认观点。
• Hydrogenation and Hydrogenolysis of 1,3-Diketones
  作者：James M. Sprague、Homer Adkins

  DOI：10.1021/ja01327a041

  日期：1934.12
• The Acylation and Alkylation of Beta Diketones and Beta Sulfonyl Ketones
  作者：E. P. Kohler、H. A. Potter

  DOI：10.1021/ja01302a023

  日期：1936.11
• Allen; Normington; Wilson, Canadian Journal of Research, 1934, vol. 11, p. 386
  作者：Allen、Normington、Wilson

  DOI：——

  日期：——