N-(2-aminophenyl)-4-methyl-thiazoline-2-thione | 215809-07-7

• 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: N-(2-aminophenyl)-4-methyl-thiazoline-2-thione
• 英文别名: 3-(2-Aminophenyl)-4-methyl-1,3-thiazole-2(3h)-thione；3-(2-aminophenyl)-4-methyl-1,3-thiazole-2-thione
• CAS: 215809-07-7
• 化学式: C₁₀H₁₀N₂S₂
• 分子量: 222.335
• InChiKey: BMMDYBPNQLEIHK-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C(Solv: ethanol (64-17-5))
• 沸点：
  369.4±44.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-aminophenyl)-4-methyl-thiazoline-2-thione 在 selenium 、 sodium tetrahydroborate 、 硫酸 、 三氟化硼乙醚 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 12.0h， 生成 4-methyl-3-[2-(4-methyl-2-selanylidene-1,3-thiazol-3-yl)phenyl]-1,3-thiazole-2-selone
  参考文献：
  名称：

  Towards Functionalised Quasi-planar Dithiadiazafulvalenes: Synthesis of Various Precursors

  摘要：

  DOI：

  10.1055/s-1998-2183
• 作为产物：
  描述：

  邻苯二胺 以 乙腈 为溶剂， 反应 15.0h， 生成 N-(2-aminophenyl)-4-methyl-thiazoline-2-thione
  参考文献：
  名称：

  Novel phenyl(thio)ureas bearing (thio)oxothiazoline group as potential BACE-1 inhibitors: synthesis and biological evaluation

  摘要：

  We report the synthesis and the beta-site amyloid precursor protein cleaving enzyme-1 inhibitory properties of novel phenyl(thio) ureas bearing 2-(thio)oxothiazoline derivatives. A library of analogues was prepared according to specific synthetic schemes and the inhibitory activity was monitored using a fluorescence resonance energy transfer assay. Several analogues show potent inhibitory activities ranging between 1 and 0.01 mu M and the activity is related to the NH acidity of the (thio) urea motif. Our results illustrate once again the close relationship between molecular recognition, complexation of the active site in enzymatic system, and organocatalysis utilizing explicit hydrogen bonding.

  DOI：

  10.3109/14756366.2011.642375

文献信息

• 3-(2-Aminophenyl)-4-methyl-1,3-thiazole-2(3H)-thione as an Ecofriendly Sulphur Transfer Agent to Prepare Alkanethiols in High Yield and High Purity
  作者：Mohammed Amine Mehdid、Ayada Djafri、Christian Roussel、Federico Andreoli

  DOI：10.3390/molecules14114634

  日期：——

  3-methyl[1,3]thiazolo[3,2-a]-[3,1]benzimidazol-9-ium salt and the alkanethiol derivative under mild conditions. The alkanethiol and the heteroaromatic salt are easily separated by a simple extraction process. The intermediate thiazolium quaternary salts resulting from the first reaction step can be isolated in quantitative yields, affording an odourless protected form of the thiols.

  描述了一种使用标题化合物的顺序烷基化，然后闭环以定量得到相应的 3-甲基 [1,3] 噻唑并 [3,2] 来制备非常纯的线性烷硫醇和线性 α,ω-烷二硫醇的新方法-a]-[3,1]苯并咪唑-9-鎓盐和链烷硫醇衍生物在温和条件下。烷硫醇和杂芳族盐很容易通过简单的萃取过程分离。可以定量产率地分离由第一反应步骤产生的中间体噻唑鎓季盐，得到硫醇的无味保护形式。
• Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives. Part III: An alkylthiol- and thioacid-free route to diversely substituted S-alkyl thioesters
  作者：Mohammed Amine Mehdid、Ayada Djafri、Federico Andreoli、Nicolas Vanthuyne、Daniel Farran、Johannes Niebler、Andrea Buettner、Michel Giorgi、Christian Roussel

  DOI：10.1016/j.tet.2013.04.013

  日期：2013.6

  conditions and in high isolated yields the S-alkyl thioesters. An ion-pair intermediate (9-acyl-3-methyl[1,3]thiazolo[3,2-a][3,1]benzimidazol-9-ium alkylthiolate) accounts for the formation of mixed thioesters during cross-coupling experiments. S-Alkyl diversity is provided by the alkylating agent and the acyl diversity comes from the acylating agent, while the sulfur atom is provided by the heterocycle

  公开了不包含烷基硫醇或硫代羧酸作为硫源的S-烷基硫酯的无金属合成。该方法首先涉及容易获得的N-（2-氨基苯基）-4-甲基噻唑啉-2-硫酮在氮上的酰化作用，其次是所得酰胺在硫上的烷基化作用，最后是碱催化的易位反应，在非常温和的条件下，以高分离产率得到S-烷基硫酯。离子对中间体（9-酰基-3-甲基[1,3]噻唑并[3,2- a ] [3,1]苯并咪唑-9-烷基硫醇盐）解释了交叉偶联实验过程中混合硫酯的形成。 S-烷基的多样性是由烷基化剂提供的，而酰基的多样性是由酰化剂提供的，而硫原子是由杂环提供的。
• Access to <i>N</i>-Thioalkenyl and <i>N</i>-(<i>o</i>-Thio)aryl-benzimidazol-2-ones by Ring Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts and C–O Bond Cleavage of an Alkoxide
  作者：Federico Andreoli、Radia Kaid-Slimane、Fabien Coppola、Daniel Farran、Christian Roussel、Nicolas Vanthuyne

  DOI：10.1021/acs.joc.5b00221

  日期：2015.3.20

  We report herein the synthesis of highly functionalized 1,3-dihydro-2H-benzimidazol-2-ones via a ring opening of thiazolo[3,2-a]benzimidazolium or benzimidazo[2,1-b][1,3]benzothiazol-6-ium salts and an unusual C–O bond cleavage of an alkoxide. A large variety of benzimidazolones bearing an original N-thioalkenyl or N-(o-thio)aryl group was obtained in high yields. The developed chemistry provides efficient

  我们在这里报告通过噻唑并[3,2- a ]苯并咪唑鎓或苯并咪唑并[2,1- b ] [1,3]苯并噻唑的开环合成高度官能化的1,3-二氢-2H-苯并咪唑-2-酮-6-ium盐和醇盐异常的C–O键裂解。以高收率获得了多种带有原始N-硫代烯基或N-（邻硫代）芳基的苯并咪唑酮。先进的化学方法可快速有效地访问特权的苯并咪唑-2-酮骨架。
• New Route to 3-Alkylthiazolo[3,2-a]benzimidazole Derivatives
  作者：Christian Roussel、Federico Andreoli、Mihaela Roman、Maria Hristova、Nicolas Vanthuyne

  DOI：10.3390/10020327

  日期：——

  3-Alkyl-thiazolo[3,2-a]benzimidazole derivatives are obtained in high yields via the corresponding 4-alkyl-N-3-(2-aminophenyl)-thiazoline-2-thiones which are easily prepared from 1,2-diaminobenzene, CS(2) and halogenoketones. This new route compares advantageously with the classical mercaptobenzimidazole routes in term of simplicity,isolated yields and availability of the starting materials.

  3-烷基-噻唑并[3,2-a]苯并咪唑衍生物是通过相应的4-烷基-N-3-(2-氨基苯基)-噻唑啉-2-硫酮以高产率获得的，这些4-烷基-N-3-(2-氨基苯基)-噻唑啉-2-硫酮很容易从1,2-二氨基苯、CS(2) 和卤代酮。该新路线在简单性、分离产率和起始原料的可用性方面与经典的巯基苯并咪唑路线相比具有优势。
• Enantioselective cyanosilylation of aldehydes catalysed by a diastereomeric mixture of atropisomeric thioureas
  作者：Rebecca M. Steele、Chiara Monti、Cesare Gennari、Umberto Piarulli、Federico Andreoli、Nicolas Vanthuyne、Christian Roussel

  DOI：10.1016/j.tetasy.2006.03.008

  日期：2006.3

  New bifunctional atropisomeric thioureas 1 were synthesised and tested as both a mixture of diastereomers (aR/aS)-(R,R)-1 and as single diastereomers (aR)-(R,R)-1 and (aR)-(S,S)-1, in the organocatalysed, enantioselective, cyanosilylation of a range of aldehydes (aromatic and aliphatic). Moderate enantiomeric excesses (up to 69% ee) and quantitative yields were obtained. The best results were achieved

  合成并测试了新的双功能阻转异构硫脲1作为非对映异构体（a R / a S）-（R，R）-1的混合物以及作为单一非对映异构体（a R）-（R，R）-1和（a R）-（S，S）-1在一系列醛（芳族和脂族）的有机催化，对映选择性，氰基硅烷化反应中进行。获得了适度的对映体过量（至多69％ee）和定量收率。使用硫脲非对映异构体的混合物（R / aS）-（R，R）-1而不是单个非对映异构体。