2-chloro-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline | 20303-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-chloro-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline
• CAS: 20303-09-7
• 化学式: C₁₄H₁₄ClN
• 分子量: 231.725
• InChiKey: QCXXBYQVBAFZGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-chloro-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline-11-carboxylic acid 生成 2-chloro-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline
  参考文献：
  名称：

  The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives

  摘要：

  DOI：

  10.1021/jo50015a019

文献信息

• New Iridium Catalysts for the Selective Alkylation of Amines by Alcohols under Mild Conditions and for the Synthesis of Quinolines by Acceptor-less Dehydrogenative Condensation
  作者：Susanne Ruch、Torsten Irrgang、Rhett Kempe

  DOI：10.1002/chem.201402952

  日期：2014.10.6

  family of iridium catalysts stabilised by P,N‐ligands have been introduced. The ligands are based on imidazo[1,5‐b]pyridazin‐7‐amines and can be synthesised with a broad variety of substitution patterns. The catalysts were synthesised quantitatively from the protonated ligands and a commercially available iridium precursor. The catalysts mediate the alkylation of amines by alcohols under mild conditions

  引入了由P，N-配体稳定的新型铱催化剂。配体基于咪唑[1,5- b]哒嗪-7胺，可以合成多种取代方式。由质子化的配体和可商购的铱前体定量合成催化剂。催化剂在温和的条件下（70°C）介导醇将胺烷基化。另外，据报道由仲或伯醇和氨基醇合成喹啉。这种可持续的合成通过释放两当量的水和两当量的二氢来进行。研究表明，适用于氢自动转移或借用氢化学的催化剂也可能适用于无受体的脱氢缩合反应。
• Direct synthesis of ring-fused quinolines and pyridines catalyzed by <i>NN</i>_<i>H</i><i>Y</i>-ligated manganese complexes (Y = NR₂ or SR)
  作者：Zheng Wang、Qing Lin、Ning Ma、Song Liu、Mingyang Han、Xiuli Yan、Qingbin Liu、Gregory A. Solan、Wen-Hua Sun

  DOI：10.1039/d1cy01945g

  日期：——

  Four cationic manganese(I) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1–Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (where NNH is a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alcohol with a ketone or secondary alcohol; NNHS-ligated Mn-4 proved the most effective of the four catalysts

  四种阳离子锰( I )配合物，[( fac-NN H N )Mn(CO) 3 ]Br ( Mn-1 – Mn-3 ) 和 [( fac-NN H S )Mn(CO) 3 ]Br ( Mn -4 )（其中N H是 5,6,7,8-四氢-8-喹啉胺部分），已被合成并评估为通过 γ-氨基醇与酮或仲醇；NN H S -连接的Mn-4被证明是四种催化剂中最有效的。在催化剂负载量为 0.5-5.0 mol% 的情况下，反应进行得很好，并且可以耐受不同的官能团，如烷基、环烷基、烷氧基、氯化物和杂芳基。基于 DFT 计算和实验证据，提出了一种涉及无受体脱氢偶联 (ADC) 的机制。值得注意的是，这种基于锰的催化方案为广泛合成重要的取代单环、双环和三环N-杂环（包括 50 个喹啉和 26 个吡啶实例）提供了一条有前途的绿色环保途径，分离产率高达 93 %。
• [EN] NOVEL UNCHARGED REACTIVATORS AGAINST OP-INHIBITION OF HUMAN ACETYLCHOLINESTERASE<br/>[FR] NOUVEAUX RÉACTIVATEURS NON CHARGÉS CONTRE L'INHIBITION DE L'ACÉTYLCHOLINESTÉRASE HUMAINE
  申请人：UNIV STRASBOURG

  公开号：WO2015075082A1

  公开（公告）日：2015-05-28

  The present invention deals with compounds of formula (I) which are novel uncharged reactivators of human acetylcholinesterase, pharmaceutical compositions comprising said compounds, and their use for reactivating human acetylcholinesterase inhibited by at least one organophosphorus nerve agent.

  本发明涉及式(I)的化合物，这些化合物是人体乙酰胆碱酯酶的新型未带电再活化剂，包含上述化合物的药物组合物，以及它们用于再活化被至少一种有机磷神经毒剂抑制的人体乙酰胆碱酯酶的用途。
• One-pot Mannich/aza-Wittig/deaminative aromatization reactions for the synthesis of 1,2,3,4-tetrahydroacridines and cyclohepta[<i>b</i>]quinolines
  作者：Wensheng Zhang、Wei Zheng、Guoqiang Zuo、Xiaole Li、Xiaofeng Zhang、Wei Zhang

  DOI：10.1039/d2nj04082d

  日期：——

  A one-pot synthesis for the preparation of 1,2,3,4-tetrahydroacridines involving a Zr(IV)-catalyzed Mannich reaction of o-azidobenzaldehydes and arylamines with cycloketones, followed by aza-Witting cyclization and deaminative aromatization, is developed. This method can be extended for the synthesis of cyclohepta[b]quinolines.

  开发了用于制备 1,2,3,4-四氢吖啶的一锅法合成，涉及 Zr( IV ) 催化的邻叠氮基苯甲醛和芳基胺与环酮的曼尼希反应，然后是氮杂维廷环化和脱氨基芳构化。该方法可推广用于环庚[ b ]喹啉的合成。
• NOVEL UNCHARGED REACTIVATORS AGAINST OP-INHIBITION OF HUMAN ACETYLCHOLINESTERASE
  申请人：Université de Strasbourg

  公开号：EP3071558A1

  公开（公告）日：2016-09-28