1-(2,7-Dichloroquinolin-3-yl)but-3-en-1-ol | 1404111-10-9

• 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: 1-(2,7-Dichloroquinolin-3-yl)but-3-en-1-ol
• 英文别名: 1-(2,7-dichloroquinolin-3-yl)but-3-en-1-ol
• CAS: 1404111-10-9
• 化学式: C₁₃H₁₁Cl₂NO
• 分子量: 268.142
• InChiKey: GMSWSAXBCMHGFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,7-Dichloroquinolin-3-yl)but-3-en-1-ol 在 sodium sulfide 、 碘 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 6-chloro-2,2a,10,11-tetrahydrofuro[2’,4’:4,6]thiopyrano[2,3-b]quinoline
  参考文献：
  名称：

  I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines

  摘要：

  I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.041
• 作为产物：
  描述：

  2,7-二氯喹啉-3-羧醛 、 3-溴丙烯 在 indium 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2,7-Dichloroquinolin-3-yl)but-3-en-1-ol
  参考文献：
  名称：

  I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines

  摘要：

  I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.041

文献信息

• Ligand promoted and controlled palladium-catalyzed intramolecular Heck reaction of homoallyl alcohols: a facile synthesis of cyclopentaannulated quinolines
  作者：Radhey M. Singh、Atish Chandra、Neha Sharma、Bhawana Singh、Ritush Kumar

  DOI：10.1016/j.tet.2012.08.088

  日期：2012.11

  Bidentate phosphine ligands in palladium-catalyzed intramolecular Heck reactions of 2-chloroquinolin-3-yl-(1-homoallyl)alcohols are described to afford facile synthesis of 3-methylene-2,3-dihydro-1H-cyclopenta[b]quinolines in improved yields. We further observed using bulky aromatic phosphine ligand in Pd-catalyzed intermolecular Heck coupling reaction at olefinic centers with iodobenzene also favored

  描述了2-氯喹啉-3-基-（1-高烯丙基）醇在钯催化的分子内Heck反应中的双齿膦配体可轻松合成3-亚甲基-2,3-二氢-1H-环戊基[ b ]喹啉提高产量。我们进一步观察到，在Pd催化的烯烃中心分子间Heck偶联反应中，使用碘化苯与笨重的芳烃膦配体同样也非常有利于Heck产品，且收率很高。
• I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines
  作者：Mrityunjaya Asthana、Neha Sharma、Ritush Kumar、Jay Bahadur Singh、Radhey M. Singh

  DOI：10.1016/j.tetlet.2014.06.041

  日期：2014.7

  I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.