2-十二烷基-1,3-苯并噻唑 | 142023-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-十二烷基-1,3-苯并噻唑
• 英文名称: 2-n-dodecylbenzo[d]thiazole
• 英文别名: 2-Dodecyl-1,3-benzothiazole；2-dodecyl-1,3-benzothiazole
• CAS: 142023-38-9
• 化学式: C₁₉H₂₉NS
• 分子量: 303.512
• InChiKey: YMSKAIOGNNOEJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯并噻唑 、 1-碘十二烷 在 (N¹,N¹-dimethyl-N²-(quinolin-8-yl)benzene-1,2-diamino)nickel(II) chloride 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以87%的产率得到2-十二烷基-1,3-苯并噻唑
  参考文献：
  名称：

  喹啉基NNN-镍镍（II）配合物的合成：鲁棒和改进的催化剂体系，用于卤代烷与卤代烷的C–H键烷基化

  摘要：

  The quinoline-based pincer nickel(II) complexes kappa(N),kappa(N),kappa(N) -{R2N-C6H4-(mu-N)-C9H6N}NiX (((NNNQ)-N-R2)NiCl: R = Me) 2a; R = Et, 2b) were synthesized by the reaction of the ligand precursors ((NNNQ)-N-R2)H (R = Me, 1a; R = Et, 1b) with (DME)NiCl2 in the presence of Et3N. Similarly, the pincer mickel(II) derivatives ((NNNQ)-N-R2)NiX (R = Me, X = Br, 3a; R = Et, X = Br, 3b; R = Me, X = OAc, 4a) were obtained by treatment of the ligands ((NNNQ)-N-R2)H with the nickel precursor (THF)(2)NiBr2 or Ni(QAc)(2). All of these complexes were characterized by H-1 and C-13 NMR spectroscopy as well as by elemental analysis. Further, the molecular structures of 2a and 3a,b were elucidated by X-ray crystallography. Complex 2a is found to be an efficient catalyst for the direct C-H bond alkylation of substituted benzothiazoles and oxazoles with various unactivated alkyl halides containing beta-hydrogens under mild reaction conditions. The catalyst 2a is very robust and was recycled and reused five times for the alkylation reaction without a decrease in its catalytic activity. Preliminary studies reveal that the catalyst 2a acts as an active catalyst and the alkylation reaction appears to operate via a radical pathway.

  DOI：

  10.1021/acs.organomet.6b00201

文献信息

• Synthesis of Quinoline-Based NNN-Pincer Nickel(II) Complexes: A Robust and Improved Catalyst System for C–H Bond Alkylation of Azoles with Alkyl Halides
  作者：Ulhas N. Patel、Dilip K. Pandey、Rajesh G. Gonnade、Benudhar Punji

  DOI：10.1021/acs.organomet.6b00201

  日期：2016.6.13

  The quinoline-based pincer nickel(II) complexes kappa(N),kappa(N),kappa(N) -R2N-C6H4-(mu-N)-C9H6N}NiX (((NNNQ)-N-R2)NiCl: R = Me) 2a; R = Et, 2b) were synthesized by the reaction of the ligand precursors ((NNNQ)-N-R2)H (R = Me, 1a; R = Et, 1b) with (DME)NiCl2 in the presence of Et3N. Similarly, the pincer mickel(II) derivatives ((NNNQ)-N-R2)NiX (R = Me, X = Br, 3a; R = Et, X = Br, 3b; R = Me, X = OAc, 4a) were obtained by treatment of the ligands ((NNNQ)-N-R2)H with the nickel precursor (THF)(2)NiBr2 or Ni(QAc)(2). All of these complexes were characterized by H-1 and C-13 NMR spectroscopy as well as by elemental analysis. Further, the molecular structures of 2a and 3a,b were elucidated by X-ray crystallography. Complex 2a is found to be an efficient catalyst for the direct C-H bond alkylation of substituted benzothiazoles and oxazoles with various unactivated alkyl halides containing beta-hydrogens under mild reaction conditions. The catalyst 2a is very robust and was recycled and reused five times for the alkylation reaction without a decrease in its catalytic activity. Preliminary studies reveal that the catalyst 2a acts as an active catalyst and the alkylation reaction appears to operate via a radical pathway.