3-Benzyl-4-methylthiazolium bromide | 4356-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Benzyl-4-methylthiazolium bromide
• 英文别名: N-benzyl-4-methylthiazolium bromide；3-benzyl-4-methyl-1,3-thiazol-3-ium;bromide
• CAS: 4356-66-5
• 化学式: Br*C₁₁H₁₂NS
• 分子量: 270.193
• InChiKey: RNNHDVNXKHLIKX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Benzyl-4-methylthiazolium bromide 在 silver tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 3-benzyl-4-methyl-2-phenylsulfanyl-thiazolium, tetrafluoroborate
  参考文献：
  名称：

  .alpha.-Keto acid dehydrogenases: a chemical model

  摘要：

  DOI：

  10.1021/jo00322a027
• 作为产物：
  描述：

  4-甲基噻唑 、 溴甲苯 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-Benzyl-4-methylthiazolium bromide
  参考文献：
  名称：

  二芳基α-二酮与卡巴噻唑的意外反应性：发现一种新型多组分反应，可轻松合成1,4-噻嗪-3-酮†

  摘要：

  在（苯并）噻唑鎓卡宾存在的情况下，二芳基α-二酮不会发生极性反转，但会与 水有效地提供医学上相关的1,4-噻嗪-3-一杂环。优化了三套不同的条件，以根据α-二酮芳族取代基和噻唑鎓或苯并噻唑鎓底物的电子性质，以公平的价格提供优异收率的标题化合物。基于假定的关键中间体和同位素标记实验的分离和表征，还提出了合理的反应机理。

  DOI：

  10.1039/c2ob25928a

文献信息

• Facile Synthesis of Highly Substituted 3-Aminofurans from Thiazolium Salts, Aldehydes, and Dimethyl Acetylenedicarboxylate
  作者：Cheng Ma、Hanfeng Ding、Guangming Wu、Yewei Yang

  DOI：10.1021/jo051513x

  日期：2005.10.1

  A facile preparation of 3-aminofuran derivatives via multicomponent reactions of thiazole carbenes, aldehydes, and dimethyl acetylenedicarboxylate (DMAD) is reported. In this process, the thiazole carbenes, generated in situ from thiazolium salts, reacted with aldehydes and DMAD at −78 to 0 °C in CH2Cl2 to afford the substituted furans in moderate to good yields. Eight substituted thiazolium salts

  据报道，通过噻唑卡宾，醛和乙炔二羧酸二甲酯（DMAD）的多组分反应可轻松制备3-氨基呋喃衍生物。在此过程中，由噻唑鎓盐原位生成的噻唑羧化物在-78至0°C下于CH 2 Cl 2中与醛和DMAD反应，以中等至良好的产率提供取代的呋喃。在反应中使用八种取代的噻唑鎓盐作为卡宾前体。除了芳基醛以外，还研究了α ， β-不饱和醛，脂肪族醛和烯丙基，并适用于该反应。
• 1H NMR study ofcis-trans isomerization in two analogs of the thiol form of thiamine
  作者：Derald Chriss、Robert H. Miller、Richard E. Echols、Ellen Vessel

  DOI：10.1002/mrc.1270220204

  日期：1984.2

  AbstractProton magnetic resonance (1H NMR) was used to study cis‐trans isomerization in N‐methyl‐N‐(1‐methylthio‐2‐propenyl)formamide and N‐benzyl‐N‐(1‐methylthio‐2‐propenyl)formamide, two analogs of the thiol form of thiamine. Benzene dilution studies and shift reagent studies were used to make resonance assignments, which indicate that the predominant isomer for each analog has the CC bond trans to the carbonyl oxygen. Shift reagent studies, using Pr(fod)3 in CCl4 or CDCl3, suggest that the reagent may be bonding to both the nitrogen and oxygen atoms of the substrate. For some of the systems studied, varying ρ at constant temperature had the same spectral effect as varying temperature at constant ρ.
• Ukai et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1943, vol. 63, p. 296,298, 300
  作者：Ukai et al.

  DOI：——

  日期：——
• Electron-Transfer Properties of Active Aldehydes of Thiamin Coenzyme Models, and Mechanism of Formation of the Reactive Intermediates
  作者：Ikuo Nakanishi、Shinobu Itoh、Shunichi Fukuzumi

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2810::aid-chem2810>3.0.co;2-f

  日期：1999.10.1

  The active aldehydes 2a-c(-) derived from the reaction of 3-benzylthiazolium salts (1a(+): 3-benzyl-4-methylthiazolium bromide, 1b(+): 3-benzyl-4;5-dimethyIthiazolium bromide, 1c(+): 3-benzylthiazolium bromide) with o-tolualdehyde in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) are stable in deaerated MeCN at 298 K because of the steric bulkiness of the o-methyl group, which prohibits benzoin condensation with a second aldehyde molecule. The one-electron oxidation of fourteen different active aldehydes (2a-n(-)) derived from various aldehydes occurs at -0.98 to -0.77 V vs. SCE in deaerated MeCN at 298 or 233 K and leads to formation of the corresponding radical intermediates (2a-n(.)), which have been characterized by electron spin resonance (ESR spectroscopy. The rapid rates of electron exchange between 2a-c(-) and 2a-c(.) were determined by the linewidth variations of the ESR spectra of 2a-c(.) in the presence of different concentrations of 2a-c(-), demonstrating the efficient electron-transfer properties of the active aldehydes. The electron transfer from 2a(-) to an outer-sphere one-electron oxidant, [Co-II(phen)(3)](2+) (phen = 1,10-phenanthroline), whose one-electron reduction potential (E-red(o) = -0.97 V) is about the same as the one-electron oxidation potential of 2a(-) (E-ox(o) = -0.96 V), occurs efficiently to yield the corresponding Co-I complex. The observed rate constants for formation of [Co-I(phen)(3)]' agree with those for formation of the active aldehyde examined independently. This agreement indicates that rate-determining formation of 2a(-), which is a very strong reductant, precedes the highly efficient electron transfer from 2a(-) to [Co-II(phen)(3)](2+).
• Takamizawa,A. et al., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 7, p. 1356 - 1362
  作者：Takamizawa,A. et al.

  DOI：——

  日期：——