2-(pent-4-en-1-yl)benzo[d]thiazole | 1228306-55-5

• 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: 2-(pent-4-en-1-yl)benzo[d]thiazole
• 英文别名: 2-Pent-4-enyl-1,3-benzothiazole
• CAS: 1228306-55-5
• 化学式: C₁₂H₁₃NS
• 分子量: 203.308
• InChiKey: YCGODEUDNHVWKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-巯基苯并噻唑 在 hexaammonium heptamolybdate tetrahydrate 、 3DPA2FBN 、 双氧水 、 对甲苯磺酸 、 potassium hydroxide 、 lithium iodide 、 锌 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 9.0h， 生成 2-(pent-4-en-1-yl)benzo[d]thiazole
  参考文献：
  名称：

  有机锌碘化物的光氧化还原激活促进多氟芳烃和杂芳烃的自由基取代

  摘要：

  芳香族化合物在光氧化还原条件下与有机锌试剂相互作用，产生取代产物。该反应在蓝光照射下通过原位生成的有机锌试剂（巴比尔条件）进行，该试剂被光催化剂氧化，然后对芳香族底物进行自由基攻击。该方法适用于多氟化芳烃、2-氯苯并恶唑和2-磺酰基取代的苯并噻唑。

  DOI：

  10.1002/adsc.202300757

文献信息

• Mechanistic Aspects of Pincer Nickel(II)-Catalyzed C–H Bond Alkylation of Azoles with Alkyl Halides
  作者：Ulhas N. Patel、Shailja Jain、Dilip K. Pandey、Rajesh G. Gonnade、Kumar Vanka、Benudhar Punji

  DOI：10.1021/acs.organomet.8b00025

  日期：2018.3.26

  κN-C9H6N-(μ-N)-C6H4–NMe2}NiCl [(QNNNMe2)NiCl; (1)] has recently been demonstrated to be an efficient and robust catalyst for the alkylation of azoles with alkyl halides under copper-free conditions. Herein, we report the detailed mechanistic investigation for the alkylation of azoles catalyzed by (QNNNMe2)NiCl (1), which highlights an iodine-atom transfer (IAT) mechanism for the reaction involving a

  基于喹啉基钳形镍络合物，κ Ñ，κ Ñ，κ ñ - C 9 ħ 6 N-（μ-N）-C 6 H ^ 4 -NMe 2 }的NiCl [（Q NNN ME2）的NiCl; （1）]最近被证明是一种在无铜条件下用烷基卤化物将唑类烷基化的有效而稳定的催化剂。在此，我们报告了由（Q NNN ME2）NiCl（1）催化的唑烷基化的详细机理研究，该研究着重介绍了涉及Ni II的反应的碘原子转移（IAT）机理。/ Ni III工艺。氘标记实验表明苯并噻唑CH键可逆裂解，动力学研究强调了底物苯并噻唑的分数负速率顺序。通过自由基钟和外部添加剂实验验证了烷基在烷基化过程中的参与。活性中间物种（Q NNN ME2）Ni（苯并噻唑基）（5a）已被分离出来，并在结构上进行了表征。发现络合物（Q NNN ME2）Ni（苯并噻唑基）（5a）是催化剂1的静止状态。电子不同中间体的动力学分析表明，涉及5a与烷基碘反应的步
• The Nickel/Copper-Catalyzed Direct Alkylation of Heterocyclic CH Bonds
  作者：Oleg Vechorkin、Valérie Proust、Xile Hu

  DOI：10.1002/anie.200907040

  日期：——

  protocol for the cross‐coupling of non‐activated alkyl halides with heterocyclic CH bonds has been developed. The transformation is chemo‐ and regioselective and many functional groups on both coupling partners are tolerated. The method employs cheap nickel/copper catalysts, and expands significantly the scope of CH functionalization (see scheme).

  选择性太强：已开发出一种通用且直接的方案，可将未活化的烷基卤与杂环CH键交叉偶联。该转化是化学和区域选择性的，并且两个偶联伴侣上的许多官能团都是可以容忍的。该方法使用廉价的镍/铜催化剂，并大大扩展了CH功能化的范围（参见方案）。
• 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.