2-(1-hydroxybenzyl)thiamin chloride hydrochloride | 16028-23-2

• 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-(1-hydroxybenzyl)thiamin chloride hydrochloride
• CAS: 16028-23-2
• 化学式: C₁₉H₂₃N₄O₂S*ClH*Cl
• 分子量: 443.397
• InChiKey: MTFBCOLWHXLBIR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.88
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  96.14
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxybenzyl)thiamin chloride hydrochloride 在 盐酸 作用下， 生成 2-(1-hydroxybenzyl)oxythiamin
  参考文献：
  名称：

  Oka,Y. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 534 - 541

  摘要：

  DOI：

文献信息

• Studies on Pyrimidine Derivatives and Related Compounds. LXXVII. Reaction of Thiamine Analogues with Diethyl Benzoylphosphonate
  作者：AKIRA TAKAMIZAWA、HIROSHI HARADA

  DOI：10.1248/cpb.21.770

  日期：——

  Reaction of thiamine analogues (8, 14, and 17) with diethyl benzoylphosphonate (20) was carried out and an interesting difference in reactivity in aprotic solvent according to substituents and nuclei was observed.

  硫胺素类似物（8、14和17）与二乙基苯甲酰膦酸酯（20）的反应进行了研究，在非质子溶剂中观察到了根据取代基和核的不同而产生的反应活性的有趣差异。
• Studies on Vitamin B<SUB>1</SUB> and Related Compounds.CVII.Synthesis of Hydroxyethylthiamine Homologs
  作者：Yoshikazu Oka、Eiko Imamiya、Hiroshi Hirano

  DOI：10.1248/cpb.15.448

  日期：——

  Two types of dihydrothiamine derivatives, IV, VI, VIII, and V, VII, IX, were obtained by the reaction of I, II, and phenylglyoxal derivatives. On treatment with mineral acids both of those underwent hydrolysis in the presence of water, but in non-aqueous solutions thiamine was afforded under room temperature. Treatments of them with weak acids such as phosphoric acid, formic acid and acetic acid effected the conversion to the aryl homologs of hydroxyethylthiamine, XI, XII and XIII.

  通过 I、II 和苯乙醛衍生物的反应，得到了两种二氢硫胺衍生物 IV、VI、VIII 和 V、VII、IX。用矿酸处理时，这两种衍生物都会在有水的情况下发生水解，但在非水溶液中，硫胺可在室温下生成。用磷酸、甲酸和乙酸等弱酸对它们进行处理，可将它们转化为羟乙基硫胺的芳基同系物 XI、XII 和 XIII。
• Destruction of Vitamin B1 by Benzaldehyde. Reactivity of Intermediates in the Fragmentation of <i>N</i>1‘-Benzyl-2-(1-hydroxybenzyl)thiamin
  作者：Ronald Kluger、Ian F. Moore

  DOI：10.1021/ja000194i

  日期：2000.7.1

  Thiamin (vitamin B1) combines with benzaldehyde in alkaline solutions to form 2-(1-hydroxybenzyl)thiamin (HBzT), a reactive intermediate in the thiamin-catalyzed benzoin condensation. In neutral solutions, HBzT fragments into pyrimidine and thiazole constituents by cleavage of the bridging methylene−thiazole bond. The fragmentation is promoted by protonation of the pyrimidine moiety of HBzT. The N1‘-benzyl

  硫胺素（维生素 B1）在碱性溶液中与苯甲醛结合形成 2-（1-羟基苄基）硫胺素 (HBzT)，这是硫胺素催化的安息香缩合反应的反应中间体。在中性溶液中，HBzT 通过断裂亚甲基-噻唑键断裂成嘧啶和噻唑成分。HBzT 的嘧啶部分的质子化促进了断裂。HBzT 的 N1'-苄基衍生物（方案 4 中的 4，BHT）也在中性和碱性溶液中发生断裂，这与由硫胺衍生的嘧啶上的正电荷驱动的断裂一致。阴离子布朗斯台德碱催化反应（β = 0.5，对于一系列取代的醋酸盐）。观察到的 BHT 裂解的一级速率系数对缓冲液浓度的依赖性是非线性的，
• Interactions of metal ions with the intermediate of thiamine catalysis
  作者：Ning-Hai Hu、Toshio Norifusa、Katsuyuki Aoki

  DOI：10.1016/s0277-5387(99)00215-6

  日期：1999.10

  to the N(1′) site of the pyrimidine ring in each case, despite the different shapes and sizes of metal coordination units; a tetrahedral unit in the cadmium complexes, a double-metal unit consisting of two tetrahedral Hg(II) ions in the mercury complexes and a square-planar unit in the platinum complex. The HBT ligands in these complexes adopt the S conformation, as usually observed in C(2)-substituted

  摘要通过使CdX2，HgX2和K2Pt（NO2）4与2-反应制得五种化学式为Cd（HBT）X3·H2O，Hg2X5（HBT）（X = Cl，Br）和Pt（HBT）（ ）3的配合物。 （α-羟基苄基）硫胺素（HBT），硫胺素催化的活性中间体，其晶体结构通过X射线衍射测定。尽管金属配位单元的形状和尺寸不同，但金属离子在每种情况下均与嘧啶环的N（1'）位结合；镉络合物中的四面体单元，汞络合物中的两个四面体Hg（II）离子和铂络合物中的方平面单元组成的双金属单元。这些配合物中的HBT配体采用S构象，通常在硫胺素的C（2）取代衍生物中观察到，平均扭转角ϕT为±99°，andP为±175°。在所有结构中，同一结构的嘧啶环的氨基和阳离子噻唑鎓环之间存在一个“两点”阴离子桥，形式为N（4′α）–H…X1–M– X2…噻唑环（M =金属离子），是影响S构象的因素之一。嘧啶和苯环之间的堆积相互作用在分子构
• Diverting Thiamin from Catalysis to Destruction. Mechanism of Fragmentation of N(1')-Methyl-2-(1-hydroxybenzyl)thiamin
  作者：Ronald Kluger、John Francis Lam、John Paul Pezacki、Chi-Ming Yang

  DOI：10.1021/ja00151a001

  日期：1995.11

  Thiamin (1) promotes reactions involving acyl carbanion equivalents derived from benzaldehyde through a covalent intermediate, 2-(1-hydroxybenzyl)thiamin (HBzT, 2). HBzT reverts to benzaldehyde and thiamin in alkaline solution. However, in neutral solution thiamin is not released as HBzT fragments irreversibly into thiazole and pyrimidine derivatives Since thiamin is produced from HBzT only at high pH, protonation of the pyrimidine of HBzT may lead to preference for fragmentation. To test the effect of charge on the reaction pathway, N(1')-methyl-2-(1-hydroxybenzyl)thiamin (5, MBzT) was prepared. Unlike HEzT, MBzT fragments in acidic, neutral, and alkaline solutions to give ketore 3 and a substituted pyrimidinium ion. Exchange of the C(2 alpha) hydrogen for deuterium is faster than fragmentation with proton removal from C(2 alpha a necessary step preliminary to fragmentation. A mechanism that is consistent with these data converts the C(2 alpha) conjugate base of HBzT to the tautomer in which a proton is removed from the C(2 alpha) and another is added to N(3). This zwitterion apparently fragments by C-N cleavage along with a 1-2 proton shift from nitrogen to carbon. The cleavage step involves an incipient carbanion in the transition state which is stabilized by the positively charged pyrimidine. The path leading to elimination of benzaldehyde is favored only when the neutral pyrimidine is present in much higher concentration than its conjugate acid. The C(2 alpha) conjugate base of 2-(1-hydroxybenzyl)thiamin diphosphate is an intermediate in the reaction catalyzed by benzoylformate decarboxylase where fragmentation of the thiamin derivative would block the normal catalytic process. In that case, forces in the active site of the enzyme must direct reaction away from fragmentation towards release of benzaldehyce.