2,2-dimethyl-5-<(2,3,4-trimethoxyphenyl)-methylene>-1,3-dioxane-4,6-dione | 152821-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2-dimethyl-5-<(2,3,4-trimethoxyphenyl)-methylene>-1,3-dioxane-4,6-dione
• 英文别名: 5-(2,3,4-trimethoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione；2,2-dimethyl-5-(2,3,4-trimethoxybenzylidene)-1,3-dioxane-4,6-dione；5-(2,3,4-trimethoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione；2,2-dimethyl-5-[(2,3,4-trimethoxyphenyl)methylidene]-1,3-dioxane-4,6-dione
• CAS: 152821-16-4
• 化学式: C₁₆H₁₈O₇
• 分子量: 322.315
• InChiKey: YKRQNGHPSCILLN-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  550.6±50.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-<(2,3,4-trimethoxyphenyl)-methylene>-1,3-dioxane-4,6-dione 在 硫酸 、 铜 作用下， 反应 1.67h， 生成 瑞香素二甲醚
  参考文献：
  名称：

  An Efficient Preparation of Coumarins

  摘要：

  o-methoxyaryl-aldehydes (or -ketones) react in solid-phase with Meldrum's acid under mild conditions, to give benzylidene derivatives which are cyclized in high yield, with cold sulfuric acid to substituted 3-carboxycoumarins. Thermal decarboxylation, speed up by copper powder, provided an easy access to numerous coumarins.

  DOI：

  10.1080/00397919308013801
• 作为产物：
  描述：

  diisopropylidenemethylenedimalonate 、 2,3,4-三甲氧基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 以82%的产率得到2,2-dimethyl-5-<(2,3,4-trimethoxyphenyl)-methylene>-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  与环状砜的狄尔斯-阿尔德反应：VII。1-苯并噻吩1,1-二氧化物衍生物的合成

  摘要：

  5-Arylmethylene-2,2-dimethyl-1,3-dioxane-4,6-diones reacted with 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide to give the corresponding ortho-addition products, 5-aryl-2',2',7-trimethyl-3,3a,5,6-tetrahydro-2H-spiro[1-benzothiophene-4,5'-[1,3]dioxane]-4',6'-dione 1,1-dioxides. Their aminolysis resulted in opening of the 1,3-dioxane ring and formation of 4-carbamoyl-7-methyl-2,3,3a,4,5,6-hexahydro-l-benzothiophene-4-carboxylic acid 1,1-dioxide whose structure was determined by X-ray analysis. Reactions of the spiro adducts with amines and hydrazine hydrate afforded the corresponding mono- or dicarboxylic acid monoamides (hydrazide).

  DOI：

  10.1023/b:rujo.0000044549.81561.4f

文献信息

• A Practical Synthesis of α-Substituted tert-Butyl Acrylates from Meldrum’s Acid and Aldehydes
  作者：Christopher Frost、Stephen Penrose、Robert Gleave

  DOI：10.1055/s-0028-1083351

  日期：2009.2

  An expeditious synthesis of α-substituted tert-butyl acryl­ates from commercially available aldehydes and Meldrum’s acid has been established. The method benefits from a telescoped condensation-reduction sequence to afford 5-monosubstituted Meldrum’s acid derivatives followed by a Mannich-type reaction triggered by a rapid cycloreversion of the dioxinone ring on heating with tert-butyl alcohol.

  已建立了一种从商业可得的醛和Meldrum酸快速合成α-取代叔丁基丙烯酸酯的方法。该方法通过叠缩-还原序列实现，先得到5-单取代的Meldrum酸衍生物，然后在加热条件下与叔丁醇发生曼尼希型反应，触发快速环转化反应，从而形成二氧环己酮环。
• Tandem Molybdenum Catalyzed Hydrosilylations:  An Expedient Synthesis of β-Aryl Aldehydes
  作者：Christopher G. Frost、Benjamin C. Hartley

  DOI：10.1021/ol701812w

  日期：2007.10.1

  The synthesis of beta-aryl aldehydes utilizing a tandem molybdenum catalyzed hydrosilylation is described. This new functional group interconversion provides an efficient method for the two-carbon homologation of aryl aldehydes.

  描述了利用串联钼催化的氢化硅烷化合成β-芳基醛。这种新的官能团互变为芳基醛的二碳同系提供了一种有效的方法。
• Reactions of methoxybenzylidene derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione and their saturated analogs with certain nucleophilic reagents
  作者：Z. Tetere、I. Ravina、I. Rijkure、D. Zicane

  DOI：10.1007/s10593-011-0690-7

  日期：2011.3

  The reactions of the methoxybenzylidene derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione and their saturated analogs with potassium hydroxide in methanol, ammonia, and hydrazine hydrate were realized. The 1,2-bis(methoxybenzylidene)hydrazines, amides, and hydrazides of methoxybenzylidene-malonic acid, suitable for use as structural blocks in the synthesis of various structures based on them, were

  实现了2,2-二甲基-1,3-二恶烷-4,6-二酮的甲氧基亚苄基衍生物及其饱和类似物与氢氧化钾在甲醇，氨和水合肼中的反应。制备并表征了适合用作合成基于它们的各种结构的结构嵌段的甲氧基亚苄基-丙二酸的1,2-双（甲氧基亚苄基）肼，酰胺和酰肼。
• Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents
  作者：Harmeet S. Sandhu、Sameer Sapra、Mukesh Gupta、Kunal Nepali、Raju Gautam、Sunil Yadav、Raj Kumar、Sanjay M. Jachak、Manoj Chugh、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2010.06.033

  日期：2010.8

  A series of arylidene analogues of Meldrum's acid were synthesized and evaluated for in vitro antimalarial and antioxidant activities for the first time. The influence of various physico-chemical parameters such as dielectric constant (epsilon), donor number (DN), acceptor number (AN), hydrogen bond donor (HBD), hydrogen bond acceptor (HBA), and solubilizing power of the solvents on Meldrum's acid anion generation and thus on promoting the Knoevenagel condensation of Meldrum's acid with aryl aldehydes has been discussed. Five compounds 9l, 9m, 9n, 9r, and 9s were found to be most active against Plasmodium falciparum with IC(50) values in the range of 9.68-16.11 mu M. Compound 9l exhibited the most potent antimalarial activity (IC(50) 9.68 mu M). The compounds were also found to possess antioxidant activity when tested against DPPH and ABTS free radicals. (C) 2010 Elsevier Ltd. All rights reserved.
• An Efficient Preparation of Coumarins
  作者：Francis Rouessac、Anne Leclerc

  DOI：10.1080/00397919308013801

  日期：1993.11

  o-methoxyaryl-aldehydes (or -ketones) react in solid-phase with Meldrum's acid under mild conditions, to give benzylidene derivatives which are cyclized in high yield, with cold sulfuric acid to substituted 3-carboxycoumarins. Thermal decarboxylation, speed up by copper powder, provided an easy access to numerous coumarins.