2-(1-哌啶基)-4-噻唑胺 | 754954-64-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(1-哌啶基)-4-噻唑胺
• 英文名称: CT16
• 英文别名: 2-(1-Piperidinyl)-1,3-Thiazol-4-Amine；2-piperidin-1-yl-1,3-thiazol-4-amine
• CAS: 754954-64-8
• 化学式: C₈H₁₃N₃S
• mdl: MFCD09802061
• 分子量: 183.277
• InChiKey: UXCNXLNTJSYWJW-UHFFFAOYSA-N

物化性质

• 沸点：
  349.1±34.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-trifluoromethylphenyl)-3-(dimethylamino)-prop-2-en-1-one 、 2-(1-哌啶基)-4-噻唑胺 在 溶剂黄146 作用下， 反应 2.0h， 以63%的产率得到5-(4-(trifluoromethyl)phenyl)-2-(piperidin-1-yl)thiazolo[4,5-b]pyridine
  参考文献：
  名称：

  2,3-Unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines

  摘要：

  通过简单的 2,3-未取代色酮或其烯胺酮前体的正式 [3 + 3] 环缩合反应，开发出了一种不同的、具有区域选择性的方法来制备融合吡啶。

  DOI：

  10.1039/c1ob06494k

文献信息

• 3-Formylchromones, Acylpyruvates, and Chalcone as Valuable Substrates for the Syntheses of Fused Pyridines
  作者：Viktor Iaroshenko、Peter Langer、Vyacheslav Sosnovskikh、Satenik Mkrtchyan、Dmitriy Volochnyuk、Dmytro Ostrovskyi、Sergii Dudkin、Anton Kotljarov、Mariia Miliutina、Iryna Savych、Andrei Tolmachev

  DOI：10.1055/s-0029-1218842

  日期：2010.8

  The reaction of electron-rich aminoheterocycles with 1,3-CCC-dielectrophiles, such as 3-formylchromones, acylpyruvates, and chalcone, provided diversely fused pyridines. Starting from 5-amino-1-(2,3-O-isopropylidene-β-d-ribofuranosyl)-1H-pyrazole, nucleosides containing a pyrazolo[3,4-b]pyridine fragment were obtained, which can be considered as adenosine deaminase (ADA) inhibitors.

  富电子氨基异核环化合物与1,3-CCC-双电亲体（如3-甲酰基色烯、酰基丙酮酸和查尔酮）的反应生成了不同融合的吡啶。以5-氨基-1-(2,3-O-异丙烯基-β-D-核糖呋喃苷)-1H-吡唑为起始物，获得了含有吡唑[3,4-b]吡啶片段的核苷，这些核苷可以被视为腺苷脱氨酶（ADA）抑制剂。
• 3-(Dichloroacetyl)chromone; A New Building Block for the Synthesis of Formylated Purine Isosteres: Design and Synthesis of Fused α-(Formyl)pyridines
  作者：Viktor Iaroshenko、Peter Langer、Satenik Mkrtchyan、Gagik Ghazaryan、Ani Hakobyan、Aneela Maalik、Linda Supe、Alexander Villinger、Andrei Tolmachev、Dmytro Ostrovskyi、Vyacheslav Sosnovskikh、Tariel Ghochikyan

  DOI：10.1055/s-0030-1258364

  日期：2011.2

  The first synthesis of 3-(dichloroacetyl)chromone from 3-(dimethylamino)-1-(2-hydroxyphenyl)propen-1-one and dichloroacetyl chloride is described. The reaction of electron-rich aminoheterocycles with 3-(dichloroacetyl)chromone provides a set of diverse fused pyridines bearing the CHCl2-substituent at the α-position of the pyridine core. Subsequent hydrolysis leads to the formation of annulated α-(formyl)pyridines

  描述了由3-（二甲基氨基）-1-（2-羟基苯基）丙烯-1-酮和二氯乙酰氯首次合成3-（二氯乙酰基）色酮。富电子的氨基杂环与3-（二氯乙酰基）色酮的反应提供了一组不同的稠合吡啶，其在吡啶核的α-位带有CHCl 2-取代基。随后的水解导致环状的α-（甲酰基）吡啶的形成。 3-（二氯乙酰基）色酮-4 H -1-苯并吡喃-4-酮-杂环胺-稠合吡啶-环化反应
• 3-Methoxalylchromone—a novel versatile reagent for the regioselective purine isostere synthesis
  作者：Satenik Mkrtchyan、Viktor O. Iaroshenko、Sergii Dudkin、Ashot Gevorgyan、Marcelo Vilches-Herrera、Gagik Ghazaryan、Dmitriy M. Volochnyuk、Dmytro Ostrovskyi、Zeeshan Ahmed、Alexander Villinger、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1039/c0ob00379d

  日期：——

  The first synthesis of 3-methoxalylchromone was described. The reaction of the latter with electron-rich aminoheterocycles afforded a set of heteroannelated pyridines bearing a CO2Me substituent located at the α-position of the pyridine core.

  首次描述了 3-甲氧基苯丙酮的合成。后者与富含电子的氨基杂环反应后，得到了一组杂环吡啶，其吡啶核心的δ位上带有 CO2Me 取代基。
• 4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins
  作者：Viktor O. Iaroshenko、Friedrich Erben、Satenik Mkrtchyan、Ani Hakobyan、Marcelo Vilches-Herrera、Sergii Dudkin、Alina Bunescu、Alexander Villinger、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1016/j.tet.2011.08.030

  日期：2011.10

  4-chloro-3-(methoxalyl)coumarins react with electron-rich aminoheterocycles, dimethyl 1,3-acetonedicarboxylate, hydrazines, alkyl thioglycolates, and methyl sarcosinate to give a variety of 3,4-heteroannulated coumarins. The starting materials were prepared by the reaction of 4-hydroxycoumarin with trifluoroacetic anhydride and methyl 2-chloro-2-oxoacetate in the presence of trimethylsilylchloride.

  4-氯-3-（三氟乙酰基）-和4-氯-3-（甲氧烷基）香豆素与富含电子的氨基杂环，1,3-丙酮二羧酸二甲酯，肼，烷基硫代乙醇酸酯和肌氨酸甲酯合成各种3， 4异环化香豆素。在三甲基甲硅烷基氯的存在下，通过4-羟基香豆素与三氟乙酸酐和2-氯-2-氧代乙酸甲酯的反应制备起始原料。报道了NMR研究和X射线晶体学分析。
• Translating Planar Heterocycles into Three‐Dimensional Analogs by Photoinduced Hydrocarboxylation**
  作者：Myriam Mikhael、Sara N. Alektiar、Charles S. Yeung、Zachary K. Wickens

  DOI：10.1002/anie.202303264

  日期：2023.7.24

  We report a new strategy that translates indoles and related heterocycles into diverse 3D analogs by dearomative hydrocarboxylation. The transformation is highly chemoselective, broad in scope, operationally simple, and readily amenable to high-throughput experimentation (HTE).

  我们报告了一种新策略，通过脱芳烃加氢羧化将吲哚和相关杂环化合物转化为多种 3D 类似物。该转化具有高度化学选择性、范围广泛、操作简单且易于进行高通量实验（HTE）。