1,4-双(2-噻唑基)-1,4-二氮杂环己烷 | 131136-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1,4-双(2-噻唑基)-1,4-二氮杂环己烷
• 英文名称: 1,4-bis(2-thiazolyl)-1,4-diazacyclohexane
• 英文别名: 1,4-Bis(2'-thiazolyl)piperazine；1,4-di(thiazol-2-yl)piperazine；2-[4-(1,3-Thiazol-2-yl)piperazin-1-yl]-1,3-thiazole
• CAS: 131136-87-3
• 化学式: C₁₀H₁₂N₄S₂
• 分子量: 252.364
• InChiKey: PQTXIAJSEHFHFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  哌嗪 、 2-氯噻唑 在 potassium tert-butylate 、 C₆₆H₉₂Cl₃N₃Pd 作用下， 以 正庚烷 为溶剂， 反应 4.0h， 以82%的产率得到1,4-双(2-噻唑基)-1,4-二氮杂环己烷
  参考文献：
  名称：

  Buchwald‐Hartwig Amination of Coordinating Heterocycles Enabled by Large‐but‐Flexible Pd‐BIAN‐NHC Catalysts**

  摘要：

  AbstractA new class of large‐but‐flexible Pd‐BIAN‐NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N‐heterocyclic carbene) has been rationally designed to enable the challenging Buchwald‐Hartwig amination of coordinating heterocycles. This robust class of BIAN‐NHC catalysts permits cross‐coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron‐deficient heterocycles containing multiple heteroatoms with BIAN‐INon (N,N′‐bis(2,6‐di(4‐heptyl)phenyl)‐7H‐acenaphtho[1,2‐d]imidazol‐8‐ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN‐NHC scaffold.

  DOI：

  10.1002/chem.202103341

文献信息

• Chemospecific and ligand free CuI catalysed heterogeneous N-arylation of amines with diheteroaryl halides at room temperature
  作者：Sanjeev K. Verma、B. N. Acharya、M. P. Kaushik

  DOI：10.1039/c0ob00859a

  日期：——

  A ligand free, copper-catalyzed N-arylation reaction of amines with diheteroaryl halides in heterogeneous medium at room temperature has been developed. The protocol is very effective for low boiling amines and useful for amines available in aqueous solution. The reaction gives chemospecific arylation of amines with diheteroaryl halides in the mixture monoheteroaryl halides, diheteroaryl halides and carbocyclic aryl halides. The reaction is also chemospecific with respect to arylation of aliphatic amines. Monoarylated piperazines were also synthesized at room temperature following this protocol.

  我们开发了一种无配体、铜催化的 N-芳基化反应，可在室温下在异相介质中使胺与二硬脂酰卤发生反应。该方案对低沸点胺非常有效，对水溶液中的胺也很有用。在单杂芳基卤化物、二杂芳基卤化物和碳环芳基卤化物的混合物中，该反应可使胺与二杂芳基卤化物发生化学特异性芳基化反应。该反应对脂肪胺的芳基化也具有化学特异性。按照此方案，还可在室温下合成单芳基化的哌嗪。
• Synthesis of New Armed Cyclopolyamines and Their Selective Extraction Properties for Metal Ions
  作者：Kiyoshi Matsumoto、Keisuke Fukuyama、Hirokazu Iida、Mitsuo Toda、J. William Lown

  DOI：10.3987/com-94-6952

  日期：——

  A variety of new armed cyclopolyamines were prepared by high pressure SNAr reactions (0.8 GPa, 100 degrees C) of cyclopolyamines with heteroaromatic halides. Certain of these agents show selective extraction properties for Hg2+ and Ag+ ions.
• High-pressure functionalization of diaza-crown ethers: new synthesis of silver(1+) ion-specific binders
  作者：Hiroshi Tsukube、Hiroyuki Minatogawa、Megumi Munakata、Mitsuo Toda、Kiyoshi Matsumoto

  DOI：10.1021/jo00028a027

  日期：1992.1

  High-pressure S(N)Ar reaction was first applied to the synthesis of a new crown ether family, which incorporated various heteroaromatics as potential cation binding sites in a unique fashion. In a CH2Cl2 liquid membrane transport experiment, several diaza-crown ethers having thiazole, oxazole, pyrazine, and pyridazine rings exhibited a perfect Ag+ ion selectivity. Cation extraction and C-13 NMR titration experiments revealed that attachment of a unique heterocycle to the diaza-crown ring, if in the proper position, significantly offered excellent Ag+ ion specificity. Since the binding and transport selectivities of these crown ethers were apparently higher than those with conventional crown ethers, the high-pressure technique provided a useful method for synthesis of a new specific crown ether family.
• Arylation of Amines and Monoarylation of Symmetrical Diamines in the Presence of Brine Solution with Diheteroaryl Halides
  作者：Sanjeev K. Verma、Ramarao Ghorpade、M. P. Kaushik

  DOI：10.1080/00397911.2013.804931

  日期：2014.9.17
• MATSUMOTO, KIYOSHI;HASHIMOTO, SHIRO;MINATOGAWA, HIROYUKI;MUNAKATA, MEGUMU+, CHEM. EXPRESS., 5,(1990) N, C. 473-476
  作者：MATSUMOTO, KIYOSHI、HASHIMOTO, SHIRO、MINATOGAWA, HIROYUKI、MUNAKATA, MEGUMU+

  DOI：——

  日期：——