5-(2-chloroethoxy)quinoline | 303751-55-5

• 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: 5-(2-chloroethoxy)quinoline
• CAS: 303751-55-5
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: GAHDHRMFYOJABT-UHFFFAOYSA-N

物化性质

• 熔点：
  69.5-72 °C
• 沸点：
  344.1±17.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-chloroethoxy)quinoline 、 3-(1,2,3,6-四氢-4-吡啶基)-1H-吡咯并[2,3-b]吡啶 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 5-{2-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-ethoxy}-quinoline
  参考文献：
  名称：

  Studies toward the discovery of the next generation of antidepressants. Part 2: Incorporating a 5-HT1A antagonist component into a class of serotonin reuptake inhibitors

  摘要：

  The design and synthesis of a novel series of indole derivatives (9) having dual 5-HT transporter reuptake and 5-HT1A antagonist activity are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00746-6
• 作为产物：
  描述：

  2-(1H-Indol-4-yloxy)-chloroethane 以41%的产率得到5-(2-chloroethoxy)quinoline
  参考文献：
  名称：

  Aryl-8-azabicyclo [3.2.1] octanes for the treatment of depression

  摘要：

  本发明包括式I1的化合物，其中A、X、n、Ar1和Ar2如本文所述。这些化合物可用于治疗抑郁症。本发明还包括含有这些化合物的配方，以及制备和使用本发明化合物的方法。

  公开号：

  US20030032645A1

文献信息

• Palladium catalyzed chloroethoxylation of aromatic and heteroaromatic chlorides: an orthogonal functionalization of a chloroethoxy linker
  作者：Bálint Pethő、Dóra Vangel、János T. Csenki、Márton Zwillinger、Zoltán Novák

  DOI：10.1039/c8ob01146j

  日期：——

  A novel disconnection based on cross-coupling chemistry was designed to access pharmaceutically relevant aryl-aminoethyl ethers. The developed palladium-catalyzed functionalization of aryl- and heteroaryl chlorides with a sodium tetrakis-(2-chloroethoxy) borate salt is orthogonal to the simple nucleophilic replacement of the chloro function of the ethylene linker. The transformation enables efficient

  设计了一种基于交叉偶联化学的新型断开连接，以获取药学上相关的芳基-氨基乙基醚。用四（2-氯乙氧基）硼酸钠钠开发的钯催化的芳基和杂芳基氯化物的官能化与乙烯接头的氯官能团的简单亲核取代正交。该转化在不存在额外的外部碱的情况下实现了有效的2-氯乙氧基化。烷基卤的随后胺取代得到2-氨基乙氧基芳烃。通过合成各种芳基和杂芳基烷基醚，包括市售药物分子的中间体，证明了该方法的适用性。
• Azaindole derivatives for the treatment of depression
  申请人：American Home Products Corporation

  公开号：US06337336B1

  公开（公告）日：2002-01-08

  Compounds useful in the treatment of diseases affected by disorders of the serotonin-affected neurological systems, such as depression and anxiety, are provided having the following formula: wherein: R1 and R2 form a carbocyclic ring of 5 to 7 carbon atoms, wherein said ring may be saturated or unsaturated and may contain one or more heteroatoms; and X is independently hydrogen, cyano, carbamoyl, halogen or alkoxy; or pharmaceutically acceptable salts thereof.

  提供了以下公式的化合物，对受到血清素受影响的神经系统紊乱所影响的疾病，如抑郁和焦虑等，具有治疗作用： 其中： R1和R2形成一个由5至7个碳原子组成的碳环，该环可以是饱和或不饱和的，并且可以含有一个或多个杂原子； X是独立的氢、氰基、氨基甲酰、卤素或烷氧基；或其药学上可接受的盐。
• Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of <i>N</i>-Aryloxyethylindolylalkylamines
  作者：Richard E. Mewshaw、Dahui Zhou、Ping Zhou、Xiaojie Shi、Geoffrey Hornby、Taylor Spangler、Rosemary Scerni、Deborah Smith、Lee E. Schechter、Terrance H. Andree

  DOI：10.1021/jm0304010

  日期：2004.7.1

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.
• Novel aryloxy-8-azabicyclo[3.2.1]oct-3-enes with 5-HT transporter and 5-HT1A affinity
  作者：Adam M. Gilbert、Thomas Coleman、Jason Kodah、Richard E. Mewshaw、Rosemary Scerni、Lee E. Schechter、Deborah L. Smith、Terrance H. Andree

  DOI：10.1016/j.bmcl.2004.08.030

  日期：2004.11

  Joining aryl 8-azabicyclo[3.2.1]oct-3-enes with aryloxyethanes and aryloxypropanes produces novel series of compounds 11 and 12 with potent 5-HT-T affinity and moderately potent 5-HT1A affinity. Moreover, several of these compounds possess functional 5-HT1A antagonism. Optimal compounds are, 4-indolyloxyethane 21, 4-indolyloxypropanes 25, and 27, which possess potent 5-HT-T affinity (5-HT-T K-i: 21: 1.2 nM, 25: 0.54 nM, 27: 0.38 nM) and good 5-HT1A affinity/antagonism (5-HT1A K-i, [S-35]GTPgammaS: E-max (%): 21: 111.1 nM, 0% 25: 173.2 nM, 0%; 27: 107 nM, 0%). (C) 2004 Elsevier Ltd. All rights reserved.
• AZAINDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1171439A1

  公开（公告）日：2002-01-16