2-chloro-3-(methoxymethyl)quinoline | 183968-27-6

• 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-3-(methoxymethyl)quinoline
• CAS: 183968-27-6
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: IPJBSSOTSOYNDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 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：

  2-chloro-3-(methoxymethyl)quinoline 在 四(三苯基膦)钯 吡啶 、 barium dihydroxide 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙二醇二甲醚 、 水 、 丙酮 为溶剂， 反应 39.0h， 生成 麦皮星酮
  参考文献：
  名称：

  2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds:  Application to the Synthesis of Nothapodytine B

  摘要：

  The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-eyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence Of O-2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkyleyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).

  DOI：

  10.1021/jo025546d
• 作为产物：
  描述：

  2-(3-methoxy-1-propynyl)formanilide 在 三乙胺 、 lithium chloride 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以37%的产率得到2-chloro-3-(methoxymethyl)quinoline
  参考文献：
  名称：

  烯烯腈的双自由基/两性离子。正式的[4 +1]环加成反应生成11H-茚并[1,2-b]喹啉及相关化合物。

  摘要：

  [反应：见正文]苯甲环化的乙炔-异腈的1，3-质子重排至相应的烯烯-异腈，然后进行环芳烃化，生成了假定的喹啉双自由基/两性离子。随后进行的分子内自由基-自由基偶联或亲电芳族取代产生了正式的[4 +1]环加成加合物，从而生成11H-茚并[1,2-b]喹啉和相关化合物。

  DOI：

  10.1021/ol035143f

文献信息

• Practical total synthesis of (+)-Camptothecin: The full story
  作者：Marco A. Ciufolini、Frank Roschangar

  DOI：10.1016/s0040-4020(97)00365-7

  日期：1997.8

  The evolution of our strategy for the synthesis of (+)-Camptothecin and related substances is presented in detail.

  详细介绍了我们合成（+）-喜树碱和相关物质的策略的演变。
• Facile palladium-mediated substitution of chlorine in 2-chloroquinolines
  作者：Marco A. Ciufolini、James W. Mitchell、Frank Roschangar

  DOI：10.1016/0040-4039(96)01937-5

  日期：1996.11

  Unlike ordinary aryl chlorides, the title hererocycles participate readily in Castro-Stephens, Stille, Suzuki, and carbonylation reactions under the catalytic influence of Pd(0).

  与普通的芳基氯化物不同，标题的杂环化合物在Pd（0）的催化作用下易于参与Castro-Stephens，Stille，Suzuki和羰基化反应。
• Biradicals/Zwitterions from Enallene-Isonitriles. Formal [4 + 1] Cycloadditions Leading to 11<i>H</i>-Indeno[1,2-<i>b</i>]quinoline and Related Compounds
  作者：Xiaoling Lu、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1021/ol035143f

  日期：2003.9.1

  the corresponding enallene-isonitriles followed by cycloaromatization generated the putative quinoline biradicals/zwitterions. A subsequent intramolecular radical-radical coupling or electrophilic aromatic substitution then gave the formal [4 + 1] cycloaddition adducts leading to 11H-indeno[1,2-b]quinoline and related compounds.

  [反应：见正文]苯甲环化的乙炔-异腈的1，3-质子重排至相应的烯烯-异腈，然后进行环芳烃化，生成了假定的喹啉双自由基/两性离子。随后进行的分子内自由基-自由基偶联或亲电芳族取代产生了正式的[4 +1]环加成加合物，从而生成11H-茚并[1,2-b]喹啉和相关化合物。
• Tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes: an efficient synthesis of 2-chloro-3-substituted quinolines
  作者：Lanying Liu、Yong Wang、Honggen Wang、Changlan Peng、Jiaji Zhao、Qiang Zhu

  DOI：10.1016/j.tetlet.2009.09.096

  日期：2009.12

  A highly efficient one-pot synthesis of 2-chloro-3-substituted quinolines has been developed by tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes, which are generated in situ by dehydration of the corresponding N-(2-ethynylphenyl)formamides. (C) 2009 Elsevier Ltd. All rights reserved.
• 2-Pyridones from Cyanoacetamides and Enecarbonyl Compounds:  Application to the Synthesis of Nothapodytine B
  作者：Lionel Carles、Kesavaram Narkunan、Sébastien Penlou、Laurence Rousset、Denis Bouchu、Marco A. Ciufolini

  DOI：10.1021/jo025546d

  日期：2002.6.1

  The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-eyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence Of O-2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkyleyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).