5-(benzo[d] [1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione | 143208-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(benzo[d] [1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione
• 英文别名: 5-Benzo[1,3]dioxol-5-ylmethylene-1,3-dimethyl-pyrimidine-2,4,6-trione；5-(1,3-benzodioxol-5-ylmethylidene)-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 143208-55-3
• 化学式: C₁₄H₁₂N₂O₅
• mdl: MFCD00552571
• 分子量: 288.26
• InChiKey: PQIXEVBCIWHNHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzo[d] [1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione 在 sodium tetrahydroborate 作用下， 以 水 、 异丙醇 为溶剂， 以85%的产率得到1,3-dimethyl-5-piperonylbarbituric acid
  参考文献：
  名称：

  Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine

  摘要：

  Reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde results in aminomethylation of C-5 to form the corresponding 5-cytisylmethylbarbituric acids. The structures of the products are found using PMR spectroscopy mid mass spectrometry. 1-Phenyl-5-(2,4-dimethoxybenzyl)-5-cytisylmethylbarbituric acid is obtained as a mixture of two steroisomers in an approximately 2:1 ratio.

  DOI：

  10.1007/bf02236429
• 作为产物：
  描述：

  胡椒醛 、 1,3-二甲基巴比妥酸 以 水 为溶剂， 反应 2.0h， 生成 5-(benzo[d] [1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione
  参考文献：
  名称：

  通过N-烷氧基α-卤代酰胺从巴比妥酸酯衍生的烯烃的多米诺氮杂-Michael / SN2环化反应合成螺环巴比妥酸酯-吡咯烷酮。

  摘要：

  巴比妥酸酯衍生的烯烃与N-烷氧基α-卤代酰胺之间的高效多米诺氮杂-MIRC（迈克尔诱导的闭环）反应以中等至极好的收率实现。该反应在温和条件下通过多米诺氮杂-迈克尔加成/分子内SN2序列顺利进行，为合成生物活性分子螺巴比妥酸酯-3-吡咯烷酮提供了实用工具。

  DOI：

  10.1039/c9ob01992h

文献信息

• Leucettamine B analogs and their carborane derivative as potential anti-cancer agents: Design, synthesis, and biological evaluation
  作者：Ming-Hua Hsu、Cheng-Ying Hsieh、Mohit Kapoor、Jui-Hsun Chang、Hsueh-Liang Chu、Tsai-Mu Cheng、Kai-Cheng Hsu、Tony Eight Lin、Fu-Yuan Tsai、Jia-Cherng Horng

  DOI：10.1016/j.bioorg.2020.103729

  日期：2020.5

  a natural product found in marine sponge Leucetta microraphis. Several of analogs of its family, such as aplysinopsine and clathridine, are medicinally active molecules which have applications in many pharmaceuticals and healthcare products; however, thus far, leucettamine B has not been studied. In this report, we describe the synthesis of a new class of analogs of leucettamine B obtained by Knoevenagel

  Leucettamine B是海洋海绵Leucetta microraphis中的天然产物。其家族中的几种类似物，例如aplysinopsine和clathridine，是具有药用活性的分子，已在许多药物和保健产品中应用。然而，迄今为止，尚未研究亮氨酰胺B。在这份报告中，我们描述了使用微波反应器通过Knoevenagel缩合反应获得的新型亮丙二胺B类似物的合成。测试了25种新合成的化合物对MDA-MB-468，SW480和Mahlavu细胞系的抗癌活性。其中，基于碳硼烷的化合物（Z）-5-（苯并[d] [1,3]二氧杂-5-基亚甲基）-3-（1-氯基碳烷基）-2-硫代-噻唑烷-4- （49）和（Z）-5-（benzo [d] [1，3]二恶唑-5-基亚甲基）-3-（2-（吡咯烷-1-基）乙基）-2-硫代噻唑烷酮-4-一（31）衍生物具有最强的抗肿瘤细胞潜力。碳硼烷衍生物49对SW480细胞系（4
• A Facile and Clean Synthesis of Pyrimidine Derivatives via Three-component Reaction in Aqueous Media
  作者：Daqing Shi、Jinwen Shi、Shaofeng Rong

  DOI：10.1002/cjoc.201090148

  日期：——

  A series of 5‐benzylidenepyrimidine‐2,4,6(1H,3H,5H)‐trione and 5,5′‐(arylmethylene) bis[6‐aminopyrimidine‐ 2,4(1H,3H)‐dione] derivatives were synthesized via the three‐component reactions of aromatic aldehyde, 6‐aminopyrimidine‐2,4‐dione and Medrum's acid in aqueous media in the presence of triethylbenzylammonium chloride. The structures of the products were affected by substituents of aromatic aldehydes

  一系列的5-亚苄基嘧啶-2,4,6（1 H，3 H，5 H）-三酮和5,5'-（芳基亚甲基）双[6-氨基嘧啶-2,4（1 H，3 H）-二酮]衍生物是在三乙基苄基氯化铵存在下，在水性介质中通过芳族醛，6-氨基嘧啶-2,4-二酮和Medrum酸的三组分反应合成的。产品的结构受芳香醛取代基的影响。
• An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions
  作者：Zhibin Huang、Qian Zhao、Gang Chen、Huiyuan Wang、Wei Lin、Lexing Xu、Hongtao Liu、Juxian Wang、Daqing Shi、Yucheng Wang

  DOI：10.3390/molecules171112704

  日期：——

  A series of novel dispirooxindoles have been synthesized through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and an α-amino acid with the dipolarophile 5-benzylidene-1,3-dimethylpyrimidine-2,4,6-trione. This method has the advantages of mild reaction conditions, high atom economy, excellent yields, and high regio- and

  通过靛红和α-氨基酸与偶极亲和物5-苄叉-1,3-二甲基嘧啶-2的脱羧缩合原位生成的偶氮甲碱叶立德的三组分1,3-偶极环加成反应合成了一系列新型二螺环吲哚,4,6-三酮。该方法具有反应条件温和、原子经济性高、产率高、区域选择性和立体选择性高等优点。
• Figueroa-Villar, Jose Daniel; Carneiro, Carisa Lopes; Cruz, Elizabete Rangel, Heterocycles, 1992, vol. 34, # 5, p. 891 - 894
  作者：Figueroa-Villar, Jose Daniel、Carneiro, Carisa Lopes、Cruz, Elizabete Rangel

  DOI：——

  日期：——
• Akabori, Chemische Berichte, 1933, vol. 66, p. 151,158
  作者：Akabori

  DOI：——

  日期：——