7-氯喹啉-3-羧酸甲酯 | 379699-99-7

• 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
• 中文名称: 7-氯喹啉-3-羧酸甲酯
• 英文名称: 7-chloroquinoline-3-carboxylic acid methyl ester
• 英文别名: methyl 7-chloroquinoline-3-carboxylate
• CAS: 379699-99-7
• 化学式: C₁₁H₈ClNO₂
• 分子量: 221.643
• InChiKey: NVCYUPDSDHADTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  N-((1R,2S,5S)-2-氨基-5-(二甲基氨基甲酰基)环己基)-5-甲基-4,5,6,7-四氢噻唑并[5,4-C]吡啶-2-甲酰胺(依度沙班杂质) 、 7-氯喹啉-3-羧酸甲酯 在 水 、 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 7-chloro-N-{(1S,2R,4S)-4-[(dimethylamino)carbonyl]-2-{[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]amino}cyclohexyl}quinoline-3-carboxamide
  参考文献：
  名称：

  设计，合成和合成顺式-1,2-二氨基环己烷衍生物作为有效的Xa因子抑制剂。第二部分：探索6–6个稠合环作为S1的替代部分

  摘要：

  合成了一系列具有S1部分6-6稠合环的顺式-1,2-二氨基环己烷衍生物，作为新颖的Xa因子（fXa）抑制剂。本文报道了合成，结构-活性关系（SAR）和理化性质，并发现了具有强大的抗fXa活性，良好的理化性质和药代动力学（PK）的化合物45c，包括降低的不良食物效应。

  DOI：

  10.1016/j.bmc.2009.10.024
• 作为产物：
  描述：

  methyl (2E)-3-(4-chlorophenyl)-2-[(toluene-4-sulfonylamino)methyl]acrylate 在 碘苯二乙酸 、 碘 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以58%的产率得到7-氯喹啉-3-羧酸甲酯
  参考文献：
  名称：

  Synthesis of quinolines from the Baylis–Hillman acetates via the oxidative cyclization of sulfonamidyl radical as the key step

  摘要：

  Ethyl 3-quinolinecarboxylates 5 were synthesized in good to moderate yields from the Baylis-Hillman acetates 1 via the oxidative cyclization reaction of the N-tosylamidyl radical, which was generated from the rearranged tosylamide derivatives 2 by iodobenzene diacetate and iodine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01314-x

文献信息

• <i>N</i>-Bromosuccinimide-Mediated Radical Cyclization of 3-Arylallyl Azides: Synthesis of 3-Substituted Quinolines
  作者：Wei-Xia Wang、Qing-Zhao Zhang、Tian-Qi Zhang、Zhan-Shan Li、Wei Zhang、Wei Yu

  DOI：10.1002/adsc.201400637

  日期：2015.1.12

  an effective means to convert methyl 2‐(azidomethyl)‐3‐arylpropenoates and 2‐(azidomethyl)‐3‐arylacrylonitriles to the corresponding iminyl radicals via α‐hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quinoline‐3‐carboxylates and quinoline‐3‐carbonitriles respectively.

  N-溴代琥珀酰亚胺的可见光照射是一种有效的手段，可通过α-氢提取并随后挤出二氮，将2-（叠氮基甲基）-3-芳基丙烯酸甲酯和2-（叠氮基甲基）-3-芳基丙烯腈转化为相应的亚氨基。如此形成的亚氨基自由基随后在芳基环上进行分子内邻位攻击，分别得到喹啉-3-羧酸甲酯和喹啉-3-腈。
• Direct Transformation of Baylis-Hillman Acetates into N-Substituted Quinolones through an SN2′ → SNAr → (Δ3,4-Δ2,3 Shift) → Oxidation Sequence
  作者：Muraleedharan Kannoth Manheri、John Napoleon

  DOI：10.1055/s-0030-1260189

  日期：2011.10

  SN2′-SNAr cyclization in the presence of alkyl or aralkyl amines, Baylis-Hillman acetates gave the corresponding 1,2-dihydroquinolines, which on simple exposure to light and oxygen afforded the corresponding 4- and 2-quinolones through sensitized oxidation or a Δ³,4-Δ²,³ shift → oxidation cascade. The mechanism of the oxidation step, the stabilities of the 1,2- and 1,4-dihydroquinolines in solution and

  当在烷基或芳烷基胺存在下进行串联S N 2'-S N Ar环化反应时，Baylis-Hillman乙酸酯可得到相应的1,2-二氢喹啉，将其简单地暴露于光和氧气下可得到相应的4-和2喹诺酮类化合物通过敏化氧化或Δ³，4-- Δ² ，³转变→氧化级联反应。讨论了氧化步骤的机理，溶液中和固态的1,2-和1,4-二氢喹啉的稳定性以及关键中间体向已知治疗剂的合成工艺。 抗生素-环化-喹啉-自由基反应-光氧化
• Encapsulating Au‐Fe ₃ O ₄ Nanodots into AIE‐active Supramolecular Assemblies: Ambient Visible‐light Harvesting “Dip‐Strip” Photocatalyst for C−C/C−N Bond Formation Reactions
  作者：Harpreet Kaur、Mandeep Kaur、Preet Kamal Walia、Manoj Kumar、Vandana Bhalla

  DOI：10.1002/asia.201801556

  日期：2019.3.15

  nanodots. Supramolecular assemblies of AIE‐active hetero‐oligophenylene derivative 6 served as reactors for the generation of Au‐Fe3O4 nanodots. The as prepared supramolecular ensemble functioned as an efficient recyclable photocatalytic system for C(sp2)−H bond activation of anilines for the construction of quinoline carboxylates. Interestingly, the “dip catalyst” prepared by depositing PTh‐co‐PANI‐6:

  本研究证明了由杂-低聚亚苯基衍生物6和Au-Fe 3 O 4纳米点组成的超分子多孔系的发展。AIE活性杂低亚苯基衍生物6的超分子组装体用作生成Au-Fe 3 O 4纳米点的反应器。所制备的超分子集合体用作苯胺的C（sp 2）-H键活化的有效可循环光催化体系，用于构造喹啉羧酸酯。有趣的是，通过沉积制备的“浸渍催化剂” PTH的共同-PANI-6：金-铁3 ö 4 滤纸上的纳米点充当可循环利用的条带（最多10个循环），用于CC / CN键形成反应。
• Polythiophene-Encapsulated Bimetallic Au-Fe₃O₄ Nano-Hybrid Materials: A Potential Tandem Photocatalytic System for Nondirected C(sp²)–H Activation for the Synthesis of Quinoline Carboxylates
  作者：Mandeep Kaur、Subhamay Pramanik、Manoj Kumar、Vandana Bhalla

  DOI：10.1021/acscatal.6b02681

  日期：2017.3.3

  Hetero-oligophenylene derivative 3 appended with thiophene moieties has been designed and synthesized which undergoes aggregation to form J-typefluorescent aggregates in in H2O/THF (7/3) media. These aggregates served as reactors for the preparation of bimetallic Au-Fe3O4 NPs. During the reduction process, aggregates of derivative 3 were oxidized to the polythiophene species 4. Interestingly, the polythiophene species 4, having a fibrous morphology, served as a shape-and morphology-directed template for assembly of bimetallic Au-Fe3O4 NPs in a flower-like arrangement. Furthermore, polythiophene-encapsulated bimetallic 4:AuFe3O4 nanohybrid materials served as an efficient and recyclable catalytic system for C(sp(2)) H bond activation of unprotected electron-rich anilines for the construction of synthetically versatile quinoline carboxylates via C H activation, carbonylation, and subsequent annulation under mild and eco-friendly conditions (aqueous media, room temperature, visible-light irradiation, and aerial conditions).
• Synthesis of quinolines from the Baylis–Hillman acetates via the oxidative cyclization of sulfonamidyl radical as the key step
  作者：Jae Nyoung Kim、Yun Mi Chung、Yang Jin Im

  DOI：10.1016/s0040-4039(02)01314-x

  日期：2002.8

  Ethyl 3-quinolinecarboxylates 5 were synthesized in good to moderate yields from the Baylis-Hillman acetates 1 via the oxidative cyclization reaction of the N-tosylamidyl radical, which was generated from the rearranged tosylamide derivatives 2 by iodobenzene diacetate and iodine. (C) 2002 Elsevier Science Ltd. All rights reserved.