5-(4-tert-butylbenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione | 430458-08-5

• 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: 5-(4-tert-butylbenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 5-[(4-tert-butylphenyl)methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 430458-08-5
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: PHNXJCYKCHHMOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  1,3-二甲基巴比妥酸 、 5-(4-tert-butylbenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 在 溴 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到5-(4-tert-butylphenyl)-1,1',3,3'-tetramethyl-1,5-dihydro-2H,2'H-spiro(furo[2,3-d]pyrimidine-6,5'-pyrimidine)-2,2',4,4',6'(1'H,3H,3'H)-pentone
  参考文献：
  名称：

  Electrocatalytic and chemical assembling of N,N′-dialkylbarbituric acids and aldehydes: efficient cascade approach to the spiro-[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′H,3H,3′H)-pentone framework

  摘要：

  Electrocatalytic assembling of aldehydes and N,N'-dialkylbarbituric acids leads to selective and efficient formation of substituted 1,5-dihydro-2H,2'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones in 70-85% yields as a result of the complex cascade process. The electrocatalytic process smoothly proceeds with aromatic aldehydes bearing both electron-donating and electron-withdrawing groups, and allows for the selective and efficient one-step formation of spirobarbiturates containing furo[2,3-d]pyrimidine scaffold, which are a perspective class of compounds with prominent pharmacological and physiological activity. The application of the effective electrocatalytic cascade method to the formation of medicinally relevant spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones is also beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel, facile and environmentally benign synthetic concept for electrocatalytic cascade reaction strategy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.057
• 作为产物：
  描述：

  对叔丁基苯甲醛 、 1,3-二甲基巴比妥酸 以 水 为溶剂， 以60 %的产率得到5-(4-tert-butylbenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  采用异硫属脲催化联烯酸酯的缩甲醛 (4+2)-环加成对映选择性合成 3,4-二氢吡喃

  摘要：

   介绍 含氧 6 环杂环化合物，如吡喃及其（部分）氢化衍生物，是生物活性（天然）产品中经常遇到的动机，或作为有价值的构建模块和合成中间体，以实现药物相关目标（方案 1A）。 1, 2, 3-5因此，开发以不对称方式获得结构多样的 6 环 O 杂环的合成方法是一项重要任务。 2, 3 （形式）(4+2)-环加成可直接获得 6 环基团，并已成功用于通过烯酮的形式 (4+2)-环加成获得手性部分氢化吡喃衍生物。 3联烯酸酯1是易于获得的多功能试剂，可以进行多种不同的环化反应。 6值得注意的是，当用（手性）路易斯碱催化剂活化时7它们可以进入不同的（正交）反应途径，具体取决于所使用的催化剂和反应伙伴， 8,9,10,11,12,13从而提供进入不同化学空间的途径依靠简单的起始材料和催化剂。已经报道了许多利用联烯酸酯进行正式环加成的应用，但不幸的是，鉴定具有高反应活性和高对映选择性的合适手性催化剂有时可能很乏味。

  DOI：

  10.1002/adsc.202400038

文献信息

• Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid (N,N'-dimethylbarbituric acid)
  作者：Ying Han、Hui Zheng、Yuan-Yuan Zhang、Chao-Guo Yan

  DOI：10.1016/j.cclet.2019.10.042

  日期：2020.5

  Abstract The three-component reaction of triphenylphosphine, dimethyl hex-2-en-4-ynedioate and arylidene N,N'-dimethylbarbituric acids in dry methylene dichloride at room temperature afforded trans-1,3-disubstituted 7,9-diazaspiro[4.5]dec-1-enes in good yields and with high diastereoselectivity. However, the similar three-component reaction with arylidene Meldrum acids resulted in a mixtures of cis/trans-1

  摘要室温下，三苯基膦，己二-2-己-4-二甲基己二酸二甲酯和亚芳基N，N'-二甲基巴比妥酸在干燥的二氯甲烷中的三组分反应得到反式1,3-二取代的7,9-二氮杂螺[4.5] ] dec-1-烯具有高收率和高非对映选择性。然而，与亚芳基Meldrum酸的类似的三组分反应导致顺式/反式1,2-二取代的7,9-二氧杂螺[4.5] dec-1-烯的混合物。另外，三苯基膦，丁二酸二炔基二甲酯和亚芳基Meldrum酸的三组分反应得到多取代的5-（三苯基-λ5-亚膦酰基）环戊-1，3-二烯。提出了一种合理的反应机理，用于形成具有不同区域选择性和非对映选择性的各种产物。
• CHARGE CONTROL AGENT AND TONER USING SAME
  申请人：Hodogaya Chemical Co., Ltd.

  公开号：EP2618219A1

  公开（公告）日：2013-07-24

  [Problems] To provide a charge control agent which contains no heavy metal component, therefore, does not adversely affect the environment and, besides, is colorless or is light-colored lending itself well to be applied to colored toners, and is little affected by the environmental conditions, and exhibits the effect of imparting high charging power even when it is used for polymerized toners. [Means for Solution] The charge control agent comprises a barbituric acid derivative represented by the following general formula (1): wherein R1 to R8 are alkyl groups, cycloalkyl groups or aryl groups, V, W, X, Y and Z are carbon atoms or nitrogen atoms, at least two of which being carbon atoms, and p, q, r, s and t are the numbers of 0 or 1.

  [问题]提供一种电荷控制剂，它不含重金属成分，因此不会对环境造成不利影响，此外，它是无色或浅色的，可以很好地应用于有色墨粉，并且受环境条件的影响很小，即使用于聚合墨粉，也能显示出赋予高电荷功率的效果。 [解决方法]电荷控制剂包括由以下通式（1）表示的巴比妥酸衍生物： 其中 R1 至 R8 为烷基、环烷基或芳基、 V、W、X、Y 和 Z 是碳原子或氮原子，其中至少有两个是碳原子，以及 p、q、r、s 和 t 是 0 或 1 的数字。
• CHARGE CONTROL AGENT AND TONER USING THE SAME
  申请人：Kimura Ikuo

  公开号：US20130157190A1

  公开（公告）日：2013-06-20

  [Problems] To provide a charge control agent which contains no heavy metal component, therefore, does not adversely affect the environment and, besides, is colorless or is light-colored lending itself well to be applied to colored toners, and is little affected by the environmental conditions, and exhibits the effect of imparting high charging power even when it is used for polymerized toners. [Means for Solution] The charge control agent comprises a barbituric acid derivative represented by the following general formula ( 1 ): wherein R 1 to R 8 are alkyl groups, cycloalkyl groups or aryl groups, V, W, X, Y and Z are carbon atoms or nitrogen atoms, at least two of which being carbon atoms, and p, q, r, s and t are the numbers of 0 or 1. [Selected Drawing] None
• US8900785B2
  申请人：——

  公开号：US8900785B2

  公开（公告）日：2014-12-02
• Electrocatalytic and chemical assembling of N,N′-dialkylbarbituric acids and aldehydes: efficient cascade approach to the spiro-[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′H,3H,3′H)-pentone framework
  作者：Anatolii N. Vereshchagin、Michail N. Elinson、Evgeniya O. Dorofeeva、Tatiana A. Zaimovskaya、Nikita O. Stepanov、Sergey V. Gorbunov、Pavel A. Belyakov、Gennady I. Nikishin

  DOI：10.1016/j.tet.2011.11.057

  日期：2012.1

  Electrocatalytic assembling of aldehydes and N,N'-dialkylbarbituric acids leads to selective and efficient formation of substituted 1,5-dihydro-2H,2'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones in 70-85% yields as a result of the complex cascade process. The electrocatalytic process smoothly proceeds with aromatic aldehydes bearing both electron-donating and electron-withdrawing groups, and allows for the selective and efficient one-step formation of spirobarbiturates containing furo[2,3-d]pyrimidine scaffold, which are a perspective class of compounds with prominent pharmacological and physiological activity. The application of the effective electrocatalytic cascade method to the formation of medicinally relevant spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones is also beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel, facile and environmentally benign synthetic concept for electrocatalytic cascade reaction strategy. (C) 2011 Elsevier Ltd. All rights reserved.