2-(4-nitrophenyl)-1-(thiophen-2-yl)ethanol | 188848-36-4

• 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: 2-(4-nitrophenyl)-1-(thiophen-2-yl)ethanol
• 英文别名: 2-(4-Nitrophenyl)-1-thiophen-2-ylethanol
• CAS: 188848-36-4
• 化学式: C₁₂H₁₁NO₃S
• 分子量: 249.29
• InChiKey: LXKPYCIKIWANII-UHFFFAOYSA-N

物化性质

• 沸点：
  412.7±35.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-1-(thiophen-2-yl)ethanol 在 盐酸 、 氯化亚砜 、 tin(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 生成 4-[2-Imidazol-1-yl-2-(2-thienyl)ethyl]aniline
  参考文献：
  名称：

  Antifungal estrogen-like imidazoles. Synthesis and antifungal activities of thienyl and 1H-pyrrolyl derivatives of 1-aryl-2-(1H-imidazol-1-yl)ethane

  摘要：

  Reaction of arylacetyl chlorides on thiophene or pyrrole derivatives furnished 2-aryl-1-(2-thienyl)- or 2-aryl-1-(1H-pyrrol-2-yl)-1-ethanones. Reduction of ketones to the corresponding carbinols and reaction of the latter compounds with 1,1'-sulfonyl-diimidazole or 1,1'-carbonyldiimidazole gave 2-thienyl- and 1H-pyrrol-2-yl-1-aryl-2-(1H-imidazol-1-yl)ethanes, respectively. The new compounds were tested in vitro against a variety of pathogenic fungi in comparison with miconazole and bifonazole. Some 5-chloro-2-thienyl derivatives were endowed with good antifungal activity, particularly against Candida albicans and Cryptococcus neoformans.

  DOI：

  10.1016/s0223-5234(97)87541-1
• 作为产物：
  描述：

  2-(4-硝基苯基)乙酰氯 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 2-(4-nitrophenyl)-1-(thiophen-2-yl)ethanol
  参考文献：
  名称：

  Antifungal estrogen-like imidazoles. Synthesis and antifungal activities of thienyl and 1H-pyrrolyl derivatives of 1-aryl-2-(1H-imidazol-1-yl)ethane

  摘要：

  Reaction of arylacetyl chlorides on thiophene or pyrrole derivatives furnished 2-aryl-1-(2-thienyl)- or 2-aryl-1-(1H-pyrrol-2-yl)-1-ethanones. Reduction of ketones to the corresponding carbinols and reaction of the latter compounds with 1,1'-sulfonyl-diimidazole or 1,1'-carbonyldiimidazole gave 2-thienyl- and 1H-pyrrol-2-yl-1-aryl-2-(1H-imidazol-1-yl)ethanes, respectively. The new compounds were tested in vitro against a variety of pathogenic fungi in comparison with miconazole and bifonazole. Some 5-chloro-2-thienyl derivatives were endowed with good antifungal activity, particularly against Candida albicans and Cryptococcus neoformans.

  DOI：

  10.1016/s0223-5234(97)87541-1

文献信息

• Nickel-Catalyzed Reductive Benzylation of Aldehydes with Benzyl Halides and Pseudohalides
  作者：Farhad Panahi、Marzieh Bahmani、Nasser Iranpoor

  DOI：10.1002/adsc.201400970

  日期：2015.4.13

  benzylation of aromatic and aliphatic aldehydes with benzylic halides is reported using a nickel/zinc catalyst system. In addition to benzylic halides, the first report on the addition of benzylic triflates, acetates, tosylates and tritylates to aldehydes is also presented. By this new method a range of alcohols was synthesized efficiently from aldehydes and benzylic substrates at room temperature in moderate

  据报道，使用镍/锌催化剂体系可将芳族和脂族醛与苄基卤化物进行还原性苄基化反应。除苄基卤化物外，还首次报道了向醛中添加苄基三氟甲磺酸酯，乙酸酯，甲苯磺酸酯和三苯甲酸酯的方法。通过这种新方法，可以在室温下从醛和苄基底物中高效合成中度到高产率的多种醇。温和的反应条件和良好的官能团耐受性使这种镍催化的方法可用于合成各种苄醇。
• Nickel-Catalyzed Reductive Etherification of Aldehydes at Room Temperature: C–O vs C–C Bond Formation
  作者：Sajjad Rahimi、Farhad Panahi、Marzieh Bahmani、Nasser Iranpoor

  DOI：10.1021/acs.joc.7b02281

  日期：2018.1.19

  reaction of secondary and tertiary benzyl alcohols activated by 2,4,6-trichloro-1,3,5-triazine (TCT) with aldehydes in the presence of NiCl2·dmg as a precatalyst in ethylene glycol afforded ethers at room temperature. A selective C–O vs C–C bond formation was observed for the secondary and tertiary benzyl alcohols in comparison with primary ones.

  在乙二醇中作为前催化剂的NiCl 2 ·dmg存在下，由2,4,6-三氯-1,3,5-三嗪（TCT）活化的仲和叔苄醇与醛的反应在室温下提供了醚。与伯醇相比，仲和叔苄醇具有选择性的C–O和C–C键形成。
• Antifungal estrogen-like imidazoles. Synthesis and antifungal activities of thienyl and 1H-pyrrolyl derivatives of 1-aryl-2-(1H-imidazol-1-yl)ethane
  作者：R Di Santo、R Costi、M Artico、S Massa、C Musiu、F Scintu、M Putzolu、P La Colla

  DOI：10.1016/s0223-5234(97)87541-1

  日期：1997.1

  Reaction of arylacetyl chlorides on thiophene or pyrrole derivatives furnished 2-aryl-1-(2-thienyl)- or 2-aryl-1-(1H-pyrrol-2-yl)-1-ethanones. Reduction of ketones to the corresponding carbinols and reaction of the latter compounds with 1,1'-sulfonyl-diimidazole or 1,1'-carbonyldiimidazole gave 2-thienyl- and 1H-pyrrol-2-yl-1-aryl-2-(1H-imidazol-1-yl)ethanes, respectively. The new compounds were tested in vitro against a variety of pathogenic fungi in comparison with miconazole and bifonazole. Some 5-chloro-2-thienyl derivatives were endowed with good antifungal activity, particularly against Candida albicans and Cryptococcus neoformans.