(E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione | 115984-23-1

• 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: (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 1,3-Dimethyl-5-(3-phenyl-allylidene)-pyrimidine-2,4,6-trione；1,3-dimethyl-5-[(E)-3-phenylprop-2-enylidene]-1,3-diazinane-2,4,6-trione
• CAS: 115984-23-1
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: LPVZBHMLVXKEEV-RMKNXTFCSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  413.2±48.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 反应 4.0h， 以75%的产率得到(1α,2α,3β,4β)-1,3-Bis(1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,4,6-trioxo-5-pyrimidinylidenmethyl)-2,4-diphenylcyclobutan
  参考文献：
  名称：

  Kaupp, Gerd; Frey, Herbert; Behmann, Gabriele, Chemische Berichte, 1988, vol. 121, p. 2135 - 2146

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 以 乙醇 、 甲苯 为溶剂， 反应 12.0h， 生成 (E)-1,3-dimethyl-5-(3-phenylallylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

  摘要：

  A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

  DOI：

  10.1021/acs.orglett.0c02508

文献信息

• Molecular Recognition on Functionalized Self-Assembled Monolayers of Alkanethiols on Gold
  作者：Kianoush Motesharei、David C. Myles

  DOI：10.1021/ja973166h

  日期：1998.7.1

  A system for probing molecular recognition events at organic interfaces using fluorescent receptors is described. Receptors formed from the bis(2,6-diaminopyridine) amide of isophthalic acid are incorporated in mixed self-assembled monolayers (SAMs) of alkanethiols on gold and shown to interact with barbituric acid derivatives from solution. Individual parameters that affect the ability of receptors

  描述了使用荧光受体探测有机界面上的分子识别事件的系统。由间苯二甲酸的双 (2,6-二氨基吡啶) 酰胺形成的受体被纳入金上链烷硫醇的混合自组装单层 (SAM) 中，并显示出与溶液中的巴比妥酸衍生物相互作用。已经检查了影响表面受体从溶液中识别配体的能力的各个参数以及配体溶液的各种溶剂。
• Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
  作者：Branko S. Jursic、Edwin D. Stevens

  DOI：10.1016/s0040-4039(03)00111-4

  日期：2003.3

  Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate

  通过系统地研究反应条件，开发了用于获得大量取代的5-烷基和5-苄基巴比妥酸的非常有效的制备方法。该过程包括两步准备，其中第二步是还原锌粉/酸。对于制备5-烷基巴比妥酸酯，第一步是制备5-酰基或5-亚烷基巴比妥酸酯。如果5-苄基巴比妥酸酯是目标产物，则第一步包括制备5-亚苄基。无论第一步的性质如何，所有反应的合成产率均约为90％，而分离和纯化仅涉及结晶。
• [EN] COMPOUNDS FOR USE IN CANCER THERAPY<br/>[FR] COMPOSÉS POUR UTILISATION DANS LA THÉRAPIE DU CANCER
  申请人：NUHOPE LLC

  公开号：WO2013024447A1

  公开（公告）日：2013-02-21

  Provided are methods and compositions for use in therapy, and in particular for treating cancer, preferably drug-resistant cancer, and/or radiation resistant cancer. The compounds may be used for reducing tumor size in a mammalian subject and for inducing apoptosis in a tumor cell. The methods are effective on tumor cells that are resistant to drugs such as temozolomide, doxorubicin, and geldanamycin, as well as non-resistant tumor cells. Further provided are barbiturate and thiobarbiturates diene compounds for use in treating cancer, and uses, methods and compositions relating to these compounds.

  提供了用于治疗的方法和组合物，特别是用于治疗癌症，最好是药物耐药性癌症和/或放射线耐药性癌症。这些化合物可用于减小哺乳动物主体的肿瘤大小，并诱导肿瘤细胞凋亡。这些方法对于对于药物如替莫唑胺、多柔比星和格兰达霉素耐药的肿瘤细胞以及非耐药的肿瘤细胞都有效。此外，还提供了用于治疗癌症的巴比妥和硫代巴比妥二烯化合物，以及与这些化合物相关的用途、方法和组合物。
• Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts
  作者：Branko S Jursic、Donna M Neumann

  DOI：10.1016/s0040-4039(01)00621-9

  日期：2001.6

  Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).

  有效的单-和二-制备合成程序Ç通过钯和巴比土酸溶液的铂催化氢化烷基化巴比土酸衍生物（未取代的，Ñ -单和Ñ，N'二取代的巴比土酸）和羰基化合物（脂族和芳族醛和酮）。
• Chemoselective synthesis of 5,4′-imidazolinyl spirobarbiturates <i>via</i> NBS-promoted cyclization of unsaturated barbiturates and amidines
  作者：Hui Xu、Rong-Lu Huang、Zhu Shu、Ran Hong、Ze Zhang

  DOI：10.1039/d1ob00508a

  日期：——

  A selective cyclization of unsaturated barbiturates and amidines promoted by N-bromosuccinimide has been successfully developed to afford a vast variety of 5,4′-imidazolinyl spirobarbiturates in moderate to good yields. The present protocol features broad substrate scope, facile work-up procedure and mild reaction conditions, providing a novel strategy for the highly selective and efficient construction

  由N-溴代琥珀酰亚胺促进的不饱和巴比妥酸盐和脒的选择性环化已成功开发，以中等至良好的收率提供种类繁多的 5,4'-咪唑啉螺巴比妥酸盐。本协议具有广泛的底物范围、简便的后处理程序和温和的反应条件，为结构多样的螺咪唑啉的高选择性和高效构建提供了一种新策略。