2-Phenyl-2-hydroxy-4-<(2-methyl-4-aminopyrimidin-5-yl)-methyl>-5-methyl-6-(2-hy-droxyethyl)-3-oxo-2.3-dihydro-4H-1.4-thiazin | 66666-26-0

• 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: 2-Phenyl-2-hydroxy-4-<(2-methyl-4-aminopyrimidin-5-yl)-methyl>-5-methyl-6-(2-hy-droxyethyl)-3-oxo-2.3-dihydro-4H-1.4-thiazin
• 英文别名: 4-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-2-hydroxy-6-(2-hydroxy-ethyl)-5-methyl-2-phenyl-4H-[1,4]thiazin-3-one；4-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-hydroxy-6-(2-hydroxyethyl)-5-methyl-2-phenyl-1,4-thiazin-3-one
• CAS: 66666-26-0
• 化学式: C₁₉H₂₂N₄O₃S
• 分子量: 386.475
• InChiKey: BZNHGPGGGXRUEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Phenyl-2-hydroxy-4-<(2-methyl-4-aminopyrimidin-5-yl)-methyl>-5-methyl-6-(2-hy-droxyethyl)-3-oxo-2.3-dihydro-4H-1.4-thiazin 、 乙酸酐 以62%的产率得到
  参考文献：
  名称：

  TAKAMIZAWA A.; HARADA H.; MAKINO I., CHEM. AND PHARM. BULL., 1978, 26, NO 3, 722-735

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-6-(2-hydroxy-ethyl)-5-methyl-2-phenyl-4H-[1,4]thiazin-3-one 、 双氧水 以38%的产率得到
  参考文献：
  名称：

  TAKAMIZAWA A.; HARADA H.; MAKINO I., CHEM. AND PHARM. BULL., 1978, 26, NO 3, 722-735

  摘要：

  DOI：

文献信息

• Studies on pyrimidine derivatives and their related compounds. XCI. On the oxidation products of 2-substituted-1,4-thiazin-3-one derivatives.
  作者：AKIRA TAKAMIZAWA、HIROSHI HARADA、ITSUO MAKINO

  DOI：10.1248/cpb.26.722

  日期：——

  On treatment of 2-p-chlorophenylthiazinothiamine (Ib) with hydrogen peroxide, 2-hydroxy-2-p-chlorophenylthiazinothiamine (IIb) was obtained. Similar reaction products of phenyl-and methylthiazinothiamine (Ia and Ie) were reinvestigated and found to be IIb analogues (IIa and IIe, respectively). Reactions of IIa, IIb or IIe with acetic anhydride afforded the corresponding N-(2-methyl-4-aminopyrimidin-5-yl) methyl-N-(2-acetylthio-4-amino-1-methyl-1-butenyl) aryl (or methyl) oxalamide (IIIa, IIIb or IIIe, respectively). Treatment of 2-o-tolylthiazinothiamine (Ic) with hydrogen peroxide gave N-[1-(2-oxido-1, 2-oxathiolan-3-ylidene) ethyl]-N-[(2-methyl-4-aminopyrimidin-5-yl) methyl]-o-tolyloxalamide (VIIIc) as a major product and similar treatment of o-methoxyphenylthiazinothiamine (Id) with hydrogen peroxide gave 1-(2-methyl-4-aminopyrimidin-5-yl) methyl-2-methyl-3-(2-hydroxyethyl)-4-hydroxy-4-(2-methoxyphenyl)-⊿2-pyrrolin-5-one (XV). Oxidations of Ia, Ic and Id with m-chloroperbenzoic acid also gave VIIIc and the corresponding VIIIc analogues (VIIIa and VIIId, respectively). The mechanisms of these reactions are discussed as shown in Chart 2.

  用过氧化氢处理 2-对氯苯基噻嗪硫胺（Ib）后，得到 2-羟基-2-对氯苯基噻嗪硫胺（IIb）。对苯基和甲基噻嗪硫胺（Ia 和 Ie）的类似反应产物进行了重新研究，发现它们分别是 IIb 类似物（IIa 和 IIe）。将 IIa、IIb 或 IIe 与乙酸酐反应，可得到相应的 N-(2-甲基-4-氨基嘧啶-5-基)甲基-N-(2-乙酰硫基-4-氨基-1-甲基-1-丁烯基)芳基（或甲基）草酰胺（分别为 IIIa、IIIb 或 IIIe）。用过氧化氢处理 2-邻甲苯基噻嗪硫胺（Ic）可得到 N-[1-（2-氧代-1、2-(2-甲基-4-氨基嘧啶-5-基)甲基]-N-[(2-甲基-4-氨基嘧啶-5-基)甲基]-邻甲苯基柳酰胺(VIIIc)作为主要产物，用过氧化氢处理邻甲氧基苯基噻嗪硫胺(Id)得到 1-(2-甲基-4-氨基嘧啶-5-基)甲基-2-甲基-3-(2-羟乙基)-4-羟基-4-(2-甲氧基苯基)-&lrtri；2-吡咯啉-5-酮 (XV)。用间氯过苯甲酸氧化 Ia、Ic 和 Id 还可得到 VIIIc 和相应的 VIIIc 类似物（分别为 VIIIa 和 VIIId）。这些反应的机理如图 2 所示。