1-(2-n-butylthioethyl)imidazole | 27423-91-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(2-n-butylthioethyl)imidazole
• 英文别名: N-(β-Thiobutyl)-ethylimidazol；1-(β-n-butylthio)ethylimidazole；1-(2-butylsulfanyl-ethyl)-1H-imidazole；1-(2-Butylmercapto-aethyl)-1H-imidazol；1-(2-butylsulfanylethyl)imidazole
• CAS: 27423-91-2
• 化学式: C₉H₁₆N₂S
• 分子量: 184.305
• InChiKey: NNOJBKGDMABPGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2-n-butylthioethyl)imidazole 、 3-苯基丙炔腈 在 sulfur 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以97%的产率得到(Z)-3-{3-[2-(butylsulfanyl)ethyl]-2-thioxo-2,3-dihydro-1H-imidazol-1-yl}-3-phenyl-2-propenenitrile
  参考文献：
  名称：

  Three-component reaction of imidazoles, cyanophenylacetylene, and chalcogens: stereoselective synthesis of 3-alkenyl-2-imidazolethiones and -selones

  摘要：

  The three-component reaction of 1-substituted imidazoles, cyanophenylacetylene, and elemental sulfur or selenium proceeds readily (for sulfur at room temperature without solvent, and for selenium in boiling MeCN) to stereoselectively afford 3-(Z)-cyanophenylethenyl-2-imidazolethiones or -selones in yields ranging 39-97% (for thiones) and 39-84% (for selones). In this reaction, tellurium is inactive both under the above conditions and upon heating (50-55 degrees C) in DMSO, instead, only the C(2)-vinylation of the imidazole ring in up to 98% yield takes place. The Z-stereoselectivity of the reaction is close to 100% (for sulfur) and reaches 91-99% (for selenium). The reaction involves the zwitterionic adduct of imidazoles with cyanophenylacetylene, which converts to the carbene via proton transfer (from the imidazole 2 position to the carbanionic site of the zwitterion) further reacting with chalcogens. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.094
• 作为产物：
  描述：

  咪唑 、 2-氯乙基丁基硫醚 在 氢氧化钾 作用下， 生成 1-(2-n-butylthioethyl)imidazole
  参考文献：
  名称：

  芥末型发泡剂与α-氨基酸的反应。

  摘要：

  DOI：

  10.1021/ja01184a093

文献信息

• C(2)-Functionalization of 1-substituted imidazoles with cyanoacetylenes and aromatic or heteroaromatic aldehydes
  作者：Boris A. Trofimov、Ludmila V. Andriyankova、Kseniya V. Belyaeva、Anastasiya G. Mal’kina、Lina P. Nikitina、Oleg A. Dyachenko、Olga N. Kazheva、Grigorii G. Alexandrov、Gennadii V. Shilov、Andrei V. Afonin、Igor’ A. Ushakov

  DOI：10.1016/j.tet.2010.11.072

  日期：2011.2

  a hitherto unknown family of functionalized imidazole derivatives, in up to 62% yield. This three-component manifold represents a novel C(2)-functionalization of the imidazole nucleus involving zwitterionic, carbene and enol ether intermediates. Unlike the analogous reaction with aliphatic aldehydes, which gives enol ethers, in this case the latter undergo the further rearrangement to 3-(2-imidazol

  取代的咪唑（取代基为Me，Et，i- Bu，n-己基，（CH 2）2 S–Bu- n，Ph，Bn）与氰基乙炔（3-苯基- 2-丙腈和4-（1-丁氧基乙氧基）-4-甲基-2-戊腈）和芳族或杂芳族醛（苯甲醛，4-CN-苯甲醛，吡啶-3-醛）得到3-（2-咪唑基）- 3-芳基-2-酰基丙烷腈，迄今未知的官能化咪唑衍生物家族，收率高达62％。这种三组分歧管代表一种新颖的C（2）咪唑核的功能化涉及两性离子，卡宾和烯醇醚中间体。与与脂肪醛的类似反应不同，后者产生烯醇醚，在这种情况下，后者进行进一步的重排，生成3-（2-咪唑基）-3-芳基-2-酰基丙腈。