Prop-2-enyl 6-(azidomethyl)-4-oxoquinoline-1-carboxylate | 1052094-65-1

• 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: Prop-2-enyl 6-(azidomethyl)-4-oxoquinoline-1-carboxylate
• CAS: 1052094-65-1
• 化学式: C₁₄H₁₂N₄O₃
• 分子量: 284.274
• InChiKey: UACMTOLCDPGZAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲氧苯乙烯基甲基酮 、 Prop-2-enyl 6-(azidomethyl)-4-oxoquinoline-1-carboxylate 在 2,6-二甲基吡啶 、 三乙基硅基三氟甲磺酸酯 、 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of an Azide-Tagged Library of 2,3-Dihydro-4-quinolones

  摘要：

  We describe the assembly of a 960-member library of tricyclic 2,3-dihydro-4-quinolones using a combination of solution-phase high-throughput organic synthesis and parallel chromatographic purification. The library was produced with high efficiency and complete chemo- and diastereoselectivity by diversification of an azide-buffing quinolone via a sequence of [4 + 2] cycloadditions, N-acylations, and reductive aminations. The azide-functionalization of this library is designed to facilitate subsequent preparation of fluorescent or affinity probes, as well as small-molecule/surface conjugation.

  DOI：

  10.1021/jo9025447
• 作为产物：
  描述：

  C₁₄H₁₂BrNO₃ 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以78%的产率得到Prop-2-enyl 6-(azidomethyl)-4-oxoquinoline-1-carboxylate
  参考文献：
  名称：

  Synthesis of an Azide-Tagged Library of 2,3-Dihydro-4-quinolones

  摘要：

  We describe the assembly of a 960-member library of tricyclic 2,3-dihydro-4-quinolones using a combination of solution-phase high-throughput organic synthesis and parallel chromatographic purification. The library was produced with high efficiency and complete chemo- and diastereoselectivity by diversification of an azide-buffing quinolone via a sequence of [4 + 2] cycloadditions, N-acylations, and reductive aminations. The azide-functionalization of this library is designed to facilitate subsequent preparation of fluorescent or affinity probes, as well as small-molecule/surface conjugation.

  DOI：

  10.1021/jo9025447

文献信息

• [EN] METHOD FOR ASSEMBLING HIGH-PURITY CHEMICAL LIBRARIES, PROAPOPTOTIC COMPOUNDS DISCOVERED BY SAME<br/>[FR] PROCÉDÉ PERMETTANT D'ASSEMBLER DES BIBLIOTHÈQUES CHIMIQUES D'UNE GRANDE PURETÉ, ET COMPOSÉS PROAPOPTOTIQUES DÉCOUVERTS GRÂCE À CE PROCÉDÉ
  申请人：KOZMIN SERGEY

  公开号：WO2008103367A2

  公开（公告）日：2008-08-28

  (EN) The present disclosure provides novel compounds of the formula (I): wherein R0, R1, R2, R3, R4, R5, and n are as defined in the detailed description. One preferred compound of formula (Vl), referred to as triazatricyclamide A, is disclosed.(FR) Cette invention concerne des nouveaux composés représentés par la formule (I): dans cette formule, R0, R1, R2, R3, R4, R5, et n sont tels que définis dans la description détaillée. Cette invention concerne un composé privilégié représenté par la formule (Vl), le triazatricyclamide A.
• Synthesis of an Azide-Tagged Library of 2,3-Dihydro-4-quinolones
  作者：Hajoong Lee、Masato Suzuki、Jiayue Cui、Sergey A. Kozmin

  DOI：10.1021/jo9025447

  日期：2010.3.5

  We describe the assembly of a 960-member library of tricyclic 2,3-dihydro-4-quinolones using a combination of solution-phase high-throughput organic synthesis and parallel chromatographic purification. The library was produced with high efficiency and complete chemo- and diastereoselectivity by diversification of an azide-buffing quinolone via a sequence of [4 + 2] cycloadditions, N-acylations, and reductive aminations. The azide-functionalization of this library is designed to facilitate subsequent preparation of fluorescent or affinity probes, as well as small-molecule/surface conjugation.