5-benzyl-3-butylimidazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-benzyl-3-butylimidazolidine-2,4-dione
• 英文别名: 5-Benzyl-3-n-butylhydantoin；3-Butyl-5-(phenylmethyl)-2,4-imidazolidinedione
• 化学式: C₁₄H₁₈N₂O₂
• mdl: MFCD12641393
• 分子量: 246.309
• InChiKey: ZOTOLRCNCFQPTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-benzyl-3-butylimidazolidine-2,4-dione 、 碘甲烷 以 N-甲基乙酰胺 、 水 为溶剂， 以85%的产率得到5-Benzyl-3-n-butyl-1-methylhydantoin
  参考文献：
  名称：

  Treatment of immediate hypersensitivity diseases with aryl hydantoins

  摘要：

  描述了一种新的咪唑啉化合物，其化学式为（I）：##STR1##其中Ar是苯基，可以选择性地取代为来自包括C.sub.1-6烷氧基、卤素、1,3-二氧杂环戊烷-2-基、羟基C.sub.1-4烷氧基C.sub.1-4烷基、苯基、羟基、腈基、C.sub.1-4卤代烷基、C.sub.1-4烷基、C.sub.2-4烯基氧基、C.sub.1-4烷氧羰基或苯氧基，可以选择性地取代为C.sub.1-4卤代烷基、C.sub.1-4烷氧基或卤素；或是噻吩，可以选择性地取代为苯基或一个或两个C.sub.1-4烷基基团；R.sup.1和R.sup.2独立地是氢原子或一起表示化学键；R.sup.3是氢原子，C.sub.1-6烷基或C.sub.2-4烯基；R.sup.4是C.sub.1-6烷基、C.sub.2-4烯基、苯基或苄基；但要求当Ar是未取代的苯基且R.sup.4是正丁基时，R.sup.3不能是氢原子。这些化合物在治疗包括哮喘在内的即时超敏症疾病中具有用途。

  公开号：

  US04241073A1
• 作为产物：
  描述：

  DL-苯丙氨酸 、 异氰酸正丁酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 5-benzyl-3-butylimidazolidine-2,4-dione
  参考文献：
  名称：

  Treatment of immediate hypersensitivity diseases with aryl hydantoins

  摘要：

  描述了一种新的咪唑啉化合物，其化学式为（I）：##STR1##其中Ar是苯基，可以选择性地取代为来自包括C.sub.1-6烷氧基、卤素、1,3-二氧杂环戊烷-2-基、羟基C.sub.1-4烷氧基C.sub.1-4烷基、苯基、羟基、腈基、C.sub.1-4卤代烷基、C.sub.1-4烷基、C.sub.2-4烯基氧基、C.sub.1-4烷氧羰基或苯氧基，可以选择性地取代为C.sub.1-4卤代烷基、C.sub.1-4烷氧基或卤素；或是噻吩，可以选择性地取代为苯基或一个或两个C.sub.1-4烷基基团；R.sup.1和R.sup.2独立地是氢原子或一起表示化学键；R.sup.3是氢原子，C.sub.1-6烷基或C.sub.2-4烯基；R.sup.4是C.sub.1-6烷基、C.sub.2-4烯基、苯基或苄基；但要求当Ar是未取代的苯基且R.sup.4是正丁基时，R.sup.3不能是氢原子。这些化合物在治疗包括哮喘在内的即时超敏症疾病中具有用途。

  公开号：

  US04241073A1

文献信息

• Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions
  作者：Aleksandr Voronov、Vinayak Botla、Luca Montanari、Carla Carfagna、Raffaella Mancuso、Bartolo Gabriele、Giovanni Maestri、Elena Motti、Nicola Della Ca

  DOI：10.1039/d1cc04154a

  日期：——

  The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.

  这里描述了钯催化氧化羰基化未保护的 α-氨基酰胺为乙内酰脲的第一个例子。目标化合物的选择性合成是在温和条件下（1 atm CO）实现的，无需配体和碱。催化系统超越了通常导致形成对称尿素的常见反应途径。
• Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates
  作者：Manjinder Gill、Dinesh Tanwar、Anjali Ratan

  DOI：10.1055/s-0036-1588468

  日期：2017.10

  A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted ­hydantoins in good yields. By applying this method, the bioactive anticonvulsant

  报道了一种制备 3-取代、5-取代或 3,5-二取代乙内酰脲的新颖且简单的方法。它涉及 α-氨基甲酯盐酸盐与氨基甲酸酯反应生成相应的脲基衍生物，随后在碱性条件下环化以高产率生成取代的乙内酰脲。应用该方法合成了生物活性抗惊厥药物乙妥英，收率良好。该过程避免了传统的多步骤方案，并且不使用通常用于合成这些重要化合物的危险、刺激性、有毒或对水分敏感的试剂，如异氰酸酯或氯甲酸酯。
• Thenyl hydantoins and anti-asthmatic compositions thereof
  申请人：Lilly Industries Limited

  公开号：US04293563A1

  公开（公告）日：1981-10-06

  Novel hydantoin compounds are described of the formula (I): ##STR1## wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C.sub.1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C.sub.1-4 alkoxy C.sub.1-4 alkyl, phenyl, hydroxyl, nitrile, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyloxy, C.sub.1-4 alkoxycarbonyl or phenoxy optionally substituted by C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or halogen; or is thiophene optionally substituted by phenyl or by one or two C.sub.1-4 alkyl groups; R.sup.1 and R.sup.2 are independently hydrogen or taken together represent a chemical bond; R.sup.3 is hydrogen, C.sub.1-6 alkyl or C.sub.2-4 alkenyl; and R.sup.4 is C.sub.1-6 alkyl, C.sub.2-4 alkenyl, phenyl or benzyl; provided that R.sup.3 cannot be hydrogen when Ar is unsubstituted phenyl and R.sup.4 is n-butyl. The compounds are useful in the treatment of immediate hypersensitivity diseases including asthma.

  本发明涉及一种新的脲嘧啶类化合物，其化学式为(I)：##STR1## 其中Ar是苯基，该苯基可选地被选自包括C.sub.1-6烷氧基，卤素，1,3-二氧杂环-2-基，羟基C.sub.1-4烷氧基C.sub.1-4烷基，苯基，羟基，腈基，C.sub.1-4卤代烷基，C.sub.1-4烷基，C.sub.2-4烯氧基，C.sub.1-4烷氧基羧基或选自C.sub.1-4卤代烷基，C.sub.1-4烷氧基或卤素取代的苯氧基取代的基团，或是噻吩基，该噻吩基可选地被苯基或一个或两个C.sub.1-4烷基取代；R.sup.1和R.sup.2分别是氢或一起表示化学键；R.sup.3是氢，C.sub.1-6烷基或C.sub.2-4烯基；R.sup.4是C.sub.1-6烷基，C.sub.2-4烯基，苯基或苄基；但是当Ar是未取代的苯基且R.sup.4是正丁基时，R.sup.3不能是氢。这些化合物可用于治疗包括哮喘在内的即时超敏反应性疾病。
• Apparatus for multiple simultaneous synthesis
  申请人：Warner-Lambert Company

  公开号：US05567391A1

  公开（公告）日：1996-10-22

  An apparatus and method which provides a suitable location for multiple, simultaneous synthesis of compounds. The apparatus consists of: a reservoir block having a plurality of wells; a plurality of reaction tubes, usually gas dispersion tubes, having filters on their lower ends; a holder block, having a plurality of apertures; and a manifold, which may have ports to allow introduction/maintenance of a controlled environment. The manifold top wall has apertures and a detachable plate with identical apertures. The apparatus is constructed from materials which will accommodate heating, cooling, agitation, or corrosive reagents. Gaskets are placed between the components. Rods or clamps are provided for fastening the components together. Apparatus operation involves placing the filters on the lower ends of the reaction tubes in the reservoir block wells, and the upper ends passing through the holder block apertures and into the manifold. The apparatus provides in excess of 1 mg of each product with structural knowledge and control over each compound. The apparatus can be adapted to manual, semiautomatic or fully automatic performance. Using the apparatus a series of building blocks are covalently attached to a solid support. These building blocks are then modified by covalently adding additional different building blocks or chemically modifying some existing functionality until the penultimate structure is achieved. This is then cleaved from the solid support by another chemical reaction into the solution within the well yielding an array of newly synthesized individual compounds, which after postreaction modification, if necessary, are suitable for testing for activity.

  一种提供适合多个化合物同时合成的合适位置的装置和方法。该装置由以下组成：具有多个孔的储液块；多个反应管，通常为气体分散管，其下端具有过滤器；具有多个孔的支架块；以及可能具有端口以允许引入/维持受控环境的集流器。集流器顶壁具有孔和带有相同孔的可拆卸板。该装置由能够适应加热、冷却、搅拌或腐蚀试剂的材料构建。在组件之间放置垫圈。提供杆或夹具以将组件固定在一起。装置操作涉及将过滤器放置在反应管的下端，放入储液块的孔中，然后将其上端穿过支架块的孔并进入集流器。该装置可提供每种产物超过1毫克的结构知识和对每种化合物的控制。该装置可适应手动、半自动或全自动性能。使用该装置，一系列构建块被共价地附加到固体支撑上。然后通过共价地添加其他不同的构建块或化学修饰某些现有的功能来修改这些构建块，直到达到次终结构。然后通过另一种化学反应从固体支撑中将其分离到孔内的溶液中，产生一系列新合成的单个化合物，经过必要的后反应修饰后，适合进行活性测试。
• Hydantoin compounds, their preparation and pharmaceutical formulations containing them
  申请人：Lilly Industries Limited

  公开号：EP0005647A1

  公开（公告）日：1979-11-28

  Hydantoin compounds are described, having the following formula wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C1-4 alkoxy C1-4 alkyl, phenyl, hydroxyl, nitrile, C1-4 haloalkyl, C1-4 alkyl, C2-4 alkenyloxy, C1-4 alkoxycarbonyl or phenoxy optionally substituted by C1-4 haloalkyl, C1-4 alkoxy or halogen; or is thiophene optionally substituted by phenyl or by one or two C1-4 alkyl groups; R' and R2 are independently hydrogen or taken together represent a chemical bond; R3 is hydrogen, C1-6 alkyl or C2-4 alkenyl; and R4 is C1-6 alkyl, C2-4 alkenyl, phenyl or benzyl; provided that R3 cannot be hydrogen when Ar is unsubstituted phenyl and R4 is n-butyl. The compounds are useful in the prophylactic treatment of asthma in mammals.

  所述的海因化合物具有下式 其中 Ar 是苯基，可任选被最多三个基团取代，这三个基团选自 C1-6 烷氧基、卤素、1,3-二氧戊环-2-基、羟基 C1-4 烷氧基、C1-4 烷基、苯基、羟基、腈基、C1-4 卤代烷基、C1-4 烷基、C2-4 烯氧基、C1-4 烷氧羰基或任选被 C1-4 卤代烷基、C1-4 烷氧基或卤素取代的苯氧基； 或任选被苯基或一个或两个 C1-4 烷基取代的噻吩； R' 和 R2 独立为氢或共同代表一个化学键； R3 是氢、C1-6 烷基或 C2-4 烯基；以及 R4 是 C1-6 烷基、C2-4 烯基、苯基或苄基； 但当 Ar 为未取代苯基且 R4 为正丁基时，R3 不能为氢。 这些化合物可用于哺乳动物哮喘的预防性治疗。