5-(4-benzylpiperazinyl)uracil | 141692-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-(4-benzylpiperazinyl)uracil
• 英文别名: 5-(4-benzyl-piperazin-1-yl)-1H-pyrimidine-2,4-dione；5-(4-benzylpiperazin-1-yl)-1H-pyrimidine-2,4-dione
• CAS: 141692-31-1
• 化学式: C₁₅H₁₈N₄O₂
• mdl: MFCD03056013
• 分子量: 286.334
• InChiKey: BQUYEGDTBNEKRQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-benzylpiperazinyl)uracil 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 132.0h， 生成 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-(4-benzylpiperazino)uracil
  参考文献：
  名称：

  A Surprising Ring Opening Mechanism in the Formation of α-D-Arabinofuranosyl Nucleosides from 5-Substituted Uracils

  摘要：

  在三甲基硅基三氟甲磺酸酯的存在下，硅烷化的5-取代尿嘧啶衍生物6与甲基2,3,5-三-O-苯甲酰基-α-D-阿拉伯呋喃糖苷（3）反应，生成相应的5-取代1-(2,3,5-三-O-苯甲酰基-α-D-阿拉伯呋喃糖基)尿嘧啶7和非环状的2,3,5-三-O-苯甲酰基-1-O-甲基-1-(尿嘧啶-1-基)-D-阿拉伯醇9的混合物，其中C-1位的甲氧基保持完整。化合物7通过与甲醇氨反应去保护，得到8。化合物7还与Lawesson试剂反应，生成相应的4-硫-α-D-阿拉伯呋喃糖核苷14，后者通过甲醇氨处理去保护，得到核苷15。从化合物9也得到了去保护的非环状核苷10。讨论了核苷7的形成机理，并且认为非环状核苷9是中间体。

  DOI：

  10.1055/s-1992-26363
• 作为产物：
  描述：

  5-溴尿嘧啶 、 1-苄基哌嗪 反应 2.25h， 以70%的产率得到5-(4-benzylpiperazinyl)uracil
  参考文献：
  名称：

  Pedersen, Henrik; Pedersen, Erik B.; Nielsen, Carsten M., Heterocycles, 1992, vol. 34, # 2, p. 265 - 272

  摘要：

  DOI：

文献信息

• [EN] DERIVATIVES OF TRIAZINES AND URACILS, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPEUTICS<br/>[FR] DÉRIVÉS DE TRIAZINES ET D'URACILES, LEUR PRÉPARATION ET LEURS APPLICATIONS EN THÉRAPEUTIQUE HUMAINE
  申请人：PF MEDICAMENT

  公开号：WO2010006962A1

  公开（公告）日：2010-01-21

  The present invention relates to derivatives of general formula I wherein : - W represents nitrogen, - R1 represents: • a hydrogen or a linear or branched C1-C5 alkyl radical or, • a C1-C3 alkyl radical substituted with groups such as trifluoromethyl, nitrile, hydroxy, C1-C3 alcoxy, C3-C6 alkoxyalkoxy, indolyl, thiophenyl, oxothiophenyl, C1-C3 N-alkylcarbamoyl groups or, • a phenyl or pyridyl or naphthyl, or thiophenyl group optionally substituted with one or more groups such as halogen atoms, nitro, nitrile, trifluoromethyl, vinyl, methylsulfanyl, linear branched C1-C4 alkyl, linear or branched C1-C3 alkoxy groups, • a C6 2-oxocycloalkyl radical - R2 represents a methyl or heptyl, - m, n are equal to 1, - V represents CH2, - X-Y represents -N- (C=O) -, -CH-O-, - Z represents a phenyl group substituted with one or more trifluoromethyl groups, halogen atoms or linear C1-C4 alkyl groups.

  本发明涉及一般式I的衍生物，其中： - W代表氮， - R1代表： • 氢或直链或支链C1-C5烷基基团，或者 • 被三氟甲基、腈、羟基、C1-C3烷氧基、C3-C6烷氧基烷氧基、吲哚基、噻吩基、氧硫吩基、C1-C3 N-烷基氨基羰基基团取代的C1-C3烷基基团，或者 • 苯基或吡啶基或萘基，或者选择性地被一个或多个卤素原子、硝基、腈、三氟甲基、乙烯、甲硫基、直链或支链C1-C4烷基、直链或支链C1-C3烷氧基基团取代的噻吩基， • C6 2-氧代环烷基基团 - R2代表甲基或庚基， - m，n等于1， - V代表CH2， - X-Y代表-N- (C=O) -，-CH-O-，- Z代表被一个或多个三氟甲基基团、卤素原子或直链C1-C4烷基基团取代的苯基。
• DERIVATIVES OF TRIAZINES AND URACILS, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPEUTICS
  申请人：Leroy Isabelle

  公开号：US20110118266A1

  公开（公告）日：2011-05-19

  The present invention relates to derivatives of general formula I wherein: —W represents nitrogen, —R 1 represents: •a hydrogen or a linear or branched C 1 -C 5 alkyl radical or, •a C 1 -C 3 alkyl radical substituted with groups such as trifluoromethyl, nitrile, hydroxy, C 1 -C 3 alcoxy, C 3 -C 6 alkoxyalkoxy, indolyl, thiophenyl, oxothiophenyl, C 1 -C 3 N-alkylcarbamoyl groups or, •a phenyl or pyridyl or naphthyl, or thiophenyl group optionally substituted with one or more groups such as halogen atoms, nitro, nitrile, trifluoromethyl, vinyl, methylsulfanyl, linear branched C 1 -C 4 alkyl, linear or branched C 1 -C 3 alkoxy groups, •a C 6 2-oxocycloalkyl radical—R 2 represents a methyl or heptyl, —m, n are equal to 1, —V represents CH 2 , —X—Y represents —N— (C═O)—, —CH—O—, —Z represents a phenyl group substituted with one or more trifluoromethyl groups, halogen atoms or linear C 1 -C 4 alkyl groups.

  本发明涉及一般式I的衍生物，其中：-W代表氮，-R1代表：•氢或线性或支链C1-C5烷基基团，或•C1-C3烷基基团，该基团被三氟甲基，腈，羟基，C1-C3烷氧基，C3-C6烷氧基烷氧基，吲哚基，噻吩基，氧代噻吩基，C1-C3N-烷基氨基甲酰基团取代，或•苯基或吡啶基或萘基，或噻吩基，可选地取代一个或多个卤原子，硝基，腈，三氟甲基，乙烯基，甲硫基，线性支链C1-C4烷基，线性或支链C1-C3烷氧基基团，•C62-氧代环烷基基团-R2代表甲基或庚基，-m，n等于1，-V代表CH2，-X-Y代表-N-(C═O)-，-CH-O-，-Z代表一个苯基，该苯基被一个或多个三氟甲基基团，卤原子或线性C1-C4烷基基团取代。
• Derivatives of triazines and uracils, their preparation and their application in human therapeutics
  申请人：Leroy Isabelle

  公开号：US08618287B2

  公开（公告）日：2013-12-31

  The present invention relates to derivatives of general formula I wherein: —W represents nitrogen, —R1 represents: •a hydrogen or a linear or branched C1-C5 alkyl radical or, •a C1-C3 alkyl radical substituted with groups such as trifluoromethyl, nitrile, hydroxy, C1-C3 alcoxy, C3-C6 alkoxyalkoxy, indolyl, thiophenyl, oxothiophenyl, C1-C3 N-alkylcarbamoyl groups or, •a phenyl or pyridyl or naphthyl, or thiophenyl group optionally substituted with one or more groups such as halogen atoms, nitro, nitrile, trifluoromethyl, vinyl, methylsulfanyl, linear branched C1-C4 alkyl, linear or branched C1-C3 alkoxy groups, •a C6 2-oxocycloalkyl radical—R2 represents a methyl or heptyl, -m, n are equal to 1, —V represents CH2, —X—Y represents —N— (C═O)—, —CH—O—, —Z represents a phenyl group substituted with one or more trifluoromethyl groups, halogen atoms or linear C1-C4 alkyl groups.

  本发明涉及一般式I的衍生物，其中：-W代表氮，-R1代表：•氢或线性或支链C1-C5烷基基团，或•C1-C3烷基基团，该基团被取代为三氟甲基、腈、羟基、C1-C3醇基、C3-C6烷氧基、吲哚基、噻吩基、氧代噻吩基、C1-C3 N-烷基氨基羰基基团或•苯基、吡啶基或萘基或噻吩基，或选配有一个或多个卤原子、硝基、腈、三氟甲基、乙烯基、甲基硫基、线性支链C1-C4烷基、线性或支链C1-C3烷氧基基团的基团，•C6 2-氧代环烷基基团-R2代表甲基或庚基，-m，n等于1，-V代表CH2，-X-Y代表—N—（C═O）—，—CH—O—，-Z代表苯基，该苯基被取代为一个或多个三氟甲基基团、卤原子或线性C1-C4烷基基团。
• US8618287B2
  申请人：——

  公开号：US8618287B2

  公开（公告）日：2013-12-31
• A Surprising Ring Opening Mechanism in the Formation of α-D-Arabinofuranosyl Nucleosides from 5-Substituted Uracils
  作者：Per Trolle Jørgensen、Erik B. Pedersen、Claus Nielsen

  DOI：10.1055/s-1992-26363

  日期：——

  Reaction of silylated 5-substituted uracil derivatives 6 with methyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside (3) in the presence of trimethylsilyl trifluoromethanesulfonate afforded a mixture of the corresponding 5-substituted 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)uracils 7 and the acyclo 2,3,5-tri-O-benzoyl-1-O-methyl-1-(uracil-1-yl)-D-arabinitols 9 with the methoxy group intact at C-1. Compound 7 was deprotected with methanolic ammonia to give 8. Compound 7 was also reacted with Lawesson's Reagent to generate the corresponding 4-thio-α-D-arabinofuranoside nucleoside 14 which was deprotected by treatment with methanolic ammonia to give the nucleosides 15. Deprotected acyclo nucleosides 10 were likewise obtained from compounds 9. The mechanism for formation of the nucleosides 7 is discussed and the acyclo nucleosides 9 are believed to be intermediates.

  在三甲基硅基三氟甲磺酸酯的存在下，硅烷化的5-取代尿嘧啶衍生物6与甲基2,3,5-三-O-苯甲酰基-α-D-阿拉伯呋喃糖苷（3）反应，生成相应的5-取代1-(2,3,5-三-O-苯甲酰基-α-D-阿拉伯呋喃糖基)尿嘧啶7和非环状的2,3,5-三-O-苯甲酰基-1-O-甲基-1-(尿嘧啶-1-基)-D-阿拉伯醇9的混合物，其中C-1位的甲氧基保持完整。化合物7通过与甲醇氨反应去保护，得到8。化合物7还与Lawesson试剂反应，生成相应的4-硫-α-D-阿拉伯呋喃糖核苷14，后者通过甲醇氨处理去保护，得到核苷15。从化合物9也得到了去保护的非环状核苷10。讨论了核苷7的形成机理，并且认为非环状核苷9是中间体。