1-prop-2-enyl-3,4-dihydro-2H-quinolin-5-ol | 1386264-24-9

• 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-prop-2-enyl-3,4-dihydro-2H-quinolin-5-ol
• CAS: 1386264-24-9
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: RTAUWMNTAWMTIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-prop-2-enyl-3,4-dihydro-2H-quinolin-5-ol 在 4-二甲氨基吡啶 、 silver hexafluoroantimonate 、 三苯基膦氯金 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 7,8,9,10-tetrahydro-2-oxo-4-(ethyl-tert-butoxycarbonylamino)-7-(2-propen-1-yl)-2H-pyrano[3,2-f ]quinoline
  参考文献：
  名称：

  Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents

  摘要：

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.

  DOI：

  10.1021/jo3006842
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉-5-醇 在 咪唑 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-prop-2-enyl-3,4-dihydro-2H-quinolin-5-ol
  参考文献：
  名称：

  Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents

  摘要：

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.

  DOI：

  10.1021/jo3006842

文献信息

• [EN] FULL-SPECTRUM HIGH-BRIGHTNESS AND HIGH-STABILITY FLUORESCENT DYES, AND SYNTHESIS AND APPLICATION THEREOF<br/>[FR] COLORANTS FLUORESCENTS À HAUTE STABILITÉ, À HAUTE LUMINOSITÉ ET À SPECTRE COMPLET, ET SYNTHÈSE ET APPLICATION DE CEUX-CI<br/>[ZH] 一种全光谱高亮度、高稳定性荧光染料及其合成和应用
  申请人：DALIAN INST CHEM & PHYSICS CAS

  公开号：WO2020124688A1

  公开（公告）日：2020-06-25

  本发明提供了一种全光谱高亮度、高稳定性荧光染料，该染料由4-酰胺基取代萘酰亚胺类染料、双烷氧基取代的萘酰亚胺类荧光染料、双氨基取代萘酰亚胺类荧光染料、9，10-双氨基取代苝酰亚胺、六元环并罗丹明类染料、五元环并罗丹明类染料、硅基罗丹明类染料中的一种或几种按任意比混合。相比于目前的商业染料，本发明的荧光染料光稳定性更高，半峰宽更窄(25nm)，对pH、极性、温度等多种外界环境均保持不敏感性。通过Click基团、蛋白标签、药物分子等活性基团的引入，得到的功能化荧光分子具有很高的生物相容性，能够对活细胞及活体进行快速、特异性染色。此外，由于光稳定性及荧光亮度的提升，该系列染料实现了Storm，STED、SIM等多种模式下的超分辨荧光成像。
• RHODAMINE COMPOUNDS AND THEIR USE AS FLUORESCENT LABELS
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  公开（公告）日：2017-01-04
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