2,2,4,6,6-五甲基-5,6-二氢-1(2H)-嘧啶醇 | 213180-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2,2,4,6,6-五甲基-5,6-二氢-1(2H)-嘧啶醇
• 英文名称: 1-hydroxy-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine
• 英文别名: 1,2,5,6-Tetrahydro-2,2,4,6,6-pentamethyl-1-pyrimidinol；1-hydroxy-2,2,4,6,6-pentamethyl-5H-pyrimidine
• CAS: 213180-20-2
• 化学式: C₉H₁₈N₂O
• 分子量: 170.255
• InChiKey: JRGCKMZUGOWOJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,4,6,6-五甲基-5,6-二氢-1(2H)-嘧啶醇 在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 生成 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahdyro-pyridmidine-1-oxyl
  参考文献：
  名称：

  Synthesis of acetonine nitroxide radical and 1-hydroxy-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine

  摘要：

  An oxidation of acetonine with hydrogen peroxide 30% in strong basic water media in the presence of sodium tungstate with subsequent reduction of reaction product with hydrazine hydrate afforded up to 50% yields of the title hydroxyderivative. Mild oxidation of this compound with MnO2 in ether gave acetonine nitroxide radical quantitatively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02049-3
• 作为产物：
  描述：

  2,2,4,4,6-五甲基-2,3,4,5-四氢嘧啶 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 生成 2,2,4,6,6-五甲基-5,6-二氢-1(2H)-嘧啶醇
  参考文献：
  名称：

  A new nitroxide radical derived from 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine and its conversion to 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine-1-oxyl

  摘要：

  The new oxaziridine nitroxide, 2,2,4,4,6-pentamethyl-7-oxa-1,3-diaza-bicyclo[4. 1.0]heptan-3-oxyl, has been obtained in 90% yield by oxidation of 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine with MCPBA in ether. This nitroxide is stable in the solid state or in non-protic solvents. It was converted to the known 2,2,4,6,6-pentamethyl-1,2, 5,6-tetrahydro-pyrimidine-1-oxyl by successive reduction with LiAlH4 and oxidation with Ag2O, with a reproducible yield of 16% from the starting tetra-hydropyrimidine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01557-4

文献信息

• Synthesis of acetonine nitroxide radical and 1-hydroxy-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine
  作者：Leonid Volodarsky、Vilen Kosover

  DOI：10.1016/s0040-4039(99)02049-3

  日期：2000.1

  An oxidation of acetonine with hydrogen peroxide 30% in strong basic water media in the presence of sodium tungstate with subsequent reduction of reaction product with hydrazine hydrate afforded up to 50% yields of the title hydroxyderivative. Mild oxidation of this compound with MnO2 in ether gave acetonine nitroxide radical quantitatively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• SUBSTITUTED TETRAHYDROPYRIMIDINE DERIVATIVES AND THEIR USE AS POLYMERIZATION INHIBITORS FOR VINYL AROMATIC COMPOUNDS
  申请人：UNIROYAL CHEMICAL COMPANY, Inc.

  公开号：EP0968192A1

  公开（公告）日：2000-01-05
• US5847035A
  申请人：——

  公开号：US5847035A

  公开（公告）日：1998-12-08
• [EN] SUBSTITUTED TETRAHYDROPYRIMIDINE DERIVATIVES AND THEIR USE AS POLYMERIZATION INHIBITORS FOR VINYL AROMATIC COMPOUNDS<br/>[FR] DERIVES SUBSTITUES DE TETRAHYDROPYRIMIDINE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE POLYMERISATION POUR COMPOSES AROMATIQUES VINYLIQUES
  申请人：UNIROYAL CHEMICAL COMPANY, INC.

  公开号：WO1998040360A1

  公开（公告）日：1998-09-17

  (EN) The present invention is directed to substituted tetrahydropyrimidine derivatives of general formula (I) wherein R1, R2, R3, R4, R5, R6 and R7, which may be the same or different are hydrogen or alkyl, aryl, cycloalkyl, alkaryl, aralkyl or heterocyclic, or substituted derivative thereof, R6 or R7 can additionally be -OH or -NR8 wherein R8 is hydrogen, alkyl, aryl, cycloalkyl, alkaryl, aralkyl or heterocyclic, or substituted derivative thereof, or R6 and R7 together can be =O or =NOH, and any two R groups on the same or adjacent carbon atoms can be joined in a cyclic configuration, and X is oxyl or hydroxy, it being provided that at least one of R2 and R3 and at least one of R4 and R5 are other than hydrogen. These compounds are used as polymerisation inhibitors for vinyl aromatic compounds. Compounds where X = hydroxy can also be used as polymer stabilisers.(FR) La présente invention concerne des dérivés substitués de tétrahydropyrimidine correspondant à la formule (I) dans laquelle R1, R2, R3, R4, R5, R6 et R7, qui peuvent identiques ou différents, représentent de l'hydrogène ou un alkyle, un aryle, un cycloalkyle, un alcaryle, un aralkyle ou un hétérocyclique, ou un dérivé substitué de ceux-ci, R6 ou R7 peuvent en outre représenter -OH ou -NR8 où R8 représente de l'hydrogène, un alkyle, un aryle, un cycloalkyle, un alcaryle, un aralkyle ou un hétérocyclique, ou un dérivé substiutué de ceux-ci, ou bien R6 et R7 représentent ensemble =O ou =NOH; l'un quelconque des groupes contenant deux R, situés sur les mêmes atomes de carbone, ou sur des atomes adjacents, peut être réuni dans une configuration cyclique; et X représente un oxyle ou un hydroxy; et ce, sous réserve qu'au moins soit R2 soit R3 et au moins soit R4 soit R5 ne représente pas de l'hydrogène. Ces composés sont utilisés en tant qu'inhibiteurs de polymérisation de composés aromatiques vinyliques. Les composés dans lesquels X représente un hydroxy peuvent également être utilisés en tant que stabilisateurs de polymères.
• A new nitroxide radical derived from 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine and its conversion to 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine-1-oxyl
  作者：Wen-li Huang、Robert Chiarelli、André Rassat

  DOI：10.1016/s0040-4039(00)01557-4

  日期：2000.11

  The new oxaziridine nitroxide, 2,2,4,4,6-pentamethyl-7-oxa-1,3-diaza-bicyclo[4. 1.0]heptan-3-oxyl, has been obtained in 90% yield by oxidation of 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine with MCPBA in ether. This nitroxide is stable in the solid state or in non-protic solvents. It was converted to the known 2,2,4,6,6-pentamethyl-1,2, 5,6-tetrahydro-pyrimidine-1-oxyl by successive reduction with LiAlH4 and oxidation with Ag2O, with a reproducible yield of 16% from the starting tetra-hydropyrimidine. (C) 2000 Elsevier Science Ltd. All rights reserved.