hexyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate | 4450-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: hexyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
• 英文别名: hexyl orotate；2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid hexyl ester；Orotsaeurehexylester；hexyl 2,4-dioxo-1H-pyrimidine-6-carboxylate
• CAS: 4450-01-5
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: DZOWZIPXYRXFPS-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230 °C
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙烯 、 hexyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate 以 水 、 丙酮 为溶剂， 生成 、
  参考文献：
  名称：

  The [2+2] Photocycloaddition of Uracil Derivatives with Ethylene as a General Route to cis-Cyclobutane β-Amino Acids

  摘要：

  基于尿嘧啶与乙烯的[2+2]光化学反应，随后通过控制杂环的降解，已开发出一种三步法程序，用于合成一系列C1和C2取代的顺式环丁烷β-氨基酸，总体产率良好。

  DOI：

  10.1055/s-2006-941571
• 作为产物：
  描述：

  乳清酸 、 正己醇 在 盐酸 作用下， 生成 hexyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
  参考文献：
  名称：

  The [2+2] Photocycloaddition of Uracil Derivatives with Ethylene as a General Route to cis-Cyclobutane β-Amino Acids

  摘要：

  基于尿嘧啶与乙烯的[2+2]光化学反应，随后通过控制杂环的降解，已开发出一种三步法程序，用于合成一系列C1和C2取代的顺式环丁烷β-氨基酸，总体产率良好。

  DOI：

  10.1055/s-2006-941571

文献信息

• An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights
  作者：Meryem Köse、Thanigaimalai Pillaiyar、Vigneshwaran Namasivayam、Elisabetta De Filippo、Katharina Sylvester、Trond Ulven、Ivar von Kügelgen、Christa E. Müller

  DOI：10.1021/acs.jmedchem.9b01339

  日期：2020.3.12

  The orphan G protein-coupled receptor (GPCR) GPR84 is expressed on immune cells mediating proinflammatory and immunostimulatory effects. In this study, we prepared the fully efficacious, nonbiased GPR84 agonist 6-hexylamino-2,4(1H,3H)-pyrimidinedione (6) in tritium-labeled form ([H-3]PSB-1584) by hydrogenation of a hexenyl-substituted precursor with tritium gas. The radio-ligand was characterized by kinetic, saturation, and competition assays using membranes of Chinese hamster ovary cells recombinantly expressing the human GPR84. [H-3]6 reversibly labeled the receptor with high affinity (K-D 2.08 nM). Structurally diverse orthosteric and allosteric ligands, including newly designed and synthesized compounds, were studied in competition binding assays. A homology model of GPR84 was generated to perform docking studies rationalizing the experimental data. The radioligand was additionally used for labeling GPR84 in native cells and tissues. [H-3]6 constitutes the first GPR84 agonist radioligand representing a powerful tool for this poorly investigated GPCR, which has potential as a future drug target.
• [EN] URACIL DERIVATIVES AS ANTI-SEBORRHEIC ADDITIVES FOR COSMETIC PRODUCTS
  申请人：HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN

  公开号：WO1983002891A1

  公开（公告）日：1983-09-01

  (EN) The compounds are represented by the formula (I):$(8,)$wherein R1 is an alkyl group having from 1 to 18 atoms of carbon, a hydroxyalkyl group having from 1 to 4 atoms of carbon, an alkoxymethyl group having from 1 to 18 atoms of carbon, a halogenomethyl or arylalkyl group, a fluorine atom, an ester group CO2R2, wherein R2 is an alkyl residue having from 1 to 18 atoms of carbon, or an amide residue CONR3 R4, wherein R3 and R4 are hydrogen, an alkyl group having from 1 to 18 atoms of carbon, an aryl or aralkyl group or form together with the nitrogen atom a heterocyclic ring. The antiseborrheic compounds are used in a ratio from 0.01 to 20 % by weight, preferably 0.1 to 2 % by weight, based on the total weight of the composition.(FR) Les composés répondent à la formule (I):$(8,)$dans laquelle R1 représente un groupe alkyle ayant de 1 à 18 atomes de carbone, un groupe hydroxyalkyle ayant de 1 à 4 atomes de carbone, un groupe alkoxyméthyle ayant de 1 à 18 atomes de carbone, un groupe halogénométhyle ou arylalkyle, un atome de fluor, un groupe ester CO2 R2, dans lequel R2 représente un reste alkyle ayant de 1 à 18 atomes de carbone, ou un reste amide CONR3 R4, dans lequel R3 et R4 sont l'hydrogène, un groupe alkyle de 1 à 18 atomes de carbone, un groupe aryl ou aralkyle ou forment avec l'atome d'azote un anneau hétérocyclique. Les composés antiséborrhéiques sont utilisés à raison de 0,01 à 20 % en poids, de préférence 0,1 à 2 % en poids, rapporté au poids total de la composition.
• The [2+2] Photocycloaddition of Uracil Derivatives with Ethylene as a General Route to <i>cis</i>-Cyclobutane β-Amino Acids
  作者：David Aitken、Christine Gauzy、Bertrand Saby、Elisabeth Pereira、Sophie Faure

  DOI：10.1055/s-2006-941571

  日期：2006.6

  A three-step procedure, based on the [2+2]-photochemical reaction of uracils with ethylene followed by controlled degradation of the heterocyclic ring, has been developed for the synthesis of a range of C1- and C2-substituted cis-cyclobutane β-amino acids, in good overall yield.

  基于尿嘧啶与乙烯的[2+2]光化学反应，随后通过控制杂环的降解，已开发出一种三步法程序，用于合成一系列C1和C2取代的顺式环丁烷β-氨基酸，总体产率良好。