1-(benzothiazol-2-yl)piperidin-2-one | 1373621-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 1-(benzothiazol-2-yl)piperidin-2-one
• CAS: 1373621-60-3
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: JNYKKFGPNXXYSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.2
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  哌啶酮 、 苯并噻唑 在 copper diacetate 、 三苯基膦 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以50%的产率得到1-(benzothiazol-2-yl)piperidin-2-one
  参考文献：
  名称：

  Copper-catalyzed oxidative C‒H, N‒H coupling of azoles and thiophenes

  摘要：

  C-H, N-H coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)(2) and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)(2)-2PPh(3) and 4 equiv of NaOAc under O-2 or in the presence of Ag2CO3 under N-2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended pi-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag2CO3 as an additive and Cu(OAc)2-2PPh3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo C-H, N-H amidation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.001

文献信息

• Synthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation–Iodination and N-Arylation, and Properties Thereof
  作者：Ghenia Bentabed-Ababsa、Ekhlass Nassar、Ziad Fajloun、Florence Mongin、Rim Amara、Madani Hedidi、Joseph Khoury、Haçan Awad、Thierry Roisnel、Vincent Dorcet、Floris Chevallier

  DOI：10.1055/s-0036-1590798

  日期：2017.10

  solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity. Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl2·TMEDA (M = Zn or Cd; TMEDA = N,N,N′,N′-tetramethylethylenediamine)

  摘要 使用原位由MCl 2 ·TMEDA（M = Zn或Cd; TMEDA = N，N，N '，N'-四甲基乙二胺）制得的碱对吨酮，噻吨酮，芴酮，二苯甲酮，2-苯甲酰吡啶，二苯并呋喃和二苯并噻吩进行去质子化。如随后的碘解所证明的那样，以1：3的比例加入2,2,6,6-四甲基哌啶锂。不同的芳基卤化物作为氮的伙伴参与吡咯烷-2-酮的芳基化。在碘化亚铜（I）和磷酸三钾的存在下，并使用二甲基亚砜作为溶剂，该反应可以以40％至70％的产率进行。大多数产品都经过了抗微生物，抗真菌，抗氧化剂和细胞毒性（MCF-7）活性测试。 使用原位由MCl 2 ·TMEDA（M = Zn或Cd; TMEDA = N，N，N '，N'-四甲基乙二胺）制得的碱对吨酮，噻吨酮，芴酮，二苯甲酮，2-苯甲酰吡啶，二苯并呋喃和二苯并噻吩进行去质子化。如随后的碘解所证明的那样，以1：3的比例加入2,2,6,6-四甲基哌啶锂。不同的
• Copper-catalyzed oxidative C‒H, N‒H coupling of azoles and thiophenes
  作者：Shinobu Mitsuda、Taiki Fujiwara、Katsuyoshi Kimigafukuro、Daiki Monguchi、Atsunori Mori

  DOI：10.1016/j.tet.2012.03.001

  日期：2012.5

  C-H, N-H coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)(2) and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)(2)-2PPh(3) and 4 equiv of NaOAc under O-2 or in the presence of Ag2CO3 under N-2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended pi-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag2CO3 as an additive and Cu(OAc)2-2PPh3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo C-H, N-H amidation. (C) 2012 Elsevier Ltd. All rights reserved.