3-amino-6,8-dichloro-2H-chromen-2-one | 33172-49-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-amino-6,8-dichloro-2H-chromen-2-one
• 英文别名: 3-amino-6,8-dichloro-chromen-2-one；3-Amino-6,8-dichlorochromen-2-one
• CAS: 33172-49-5
• 化学式: C₉H₅Cl₂NO₂
• 分子量: 230.05
• InChiKey: VQDFFHVEKCZXKG-UHFFFAOYSA-N

物化性质

• 熔点：
  166-169 °C
• 沸点：
  430.9±45.0 °C(Predicted)
• 密度：
  1.569±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-6,8-dichloro-2H-chromen-2-one 在 盐酸 、 sodium nitrite 作用下， 以 氘代二甲亚砜 为溶剂， 反应 1.25h， 生成 3-(8-(3-aminopropanoyl)-8,9-dihydro-3H-dibenzo[b,f][1,2,3]triazolo[4,5-d]azocin-3-yl)-6,8-dichloro-2H-chromen-2-one
  参考文献：
  名称：

  Development of surface immobilized 3-azidocoumarin-based fluorogenic probe via strain promoted click chemistry

  摘要：

  A new class of imaging probe, a fluorogenic version of 1, 3-dipolar cycloaddition of azides and alkynes has been developed. 3-azidocoumarin scaffolds were selectively immobilized on the DBCO modified bead surface via SPAAC and provide direct and strong fluorescence in fluorescence microscopy. This developed click-on beads could be applied to label various biomolecules, such as nucleic acids, proteins and other molecules. To this end, 5'(7-hydroxy 3-azido coumarin) labelled DNA primer also displayed strong fluorescence upon successful immobilization on the bead surface. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.078
• 作为产物：
  描述：

  6,8-二氯-2-氧代-2H-苯并吡喃-3-羧酸 在 盐酸 、 二苯基磷酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 3-amino-6,8-dichloro-2H-chromen-2-one
  参考文献：
  名称：

  新2的合成ħ，4 ħ -苯并吡喃并[3,4- b ] yridine -1,3,5-三酮衍生物通过二氧化三碳

  摘要：

  新的2 ħ，4 ħ - [1]苯并吡喃并[3,4- b ]吡啶-1,3,5-三酮衍生物10A-F在以下三个步骤制备：新的第一制备ñ - （叔-通过香豆素-3-羧酸与二苯基磷酰叠氮化物的反应，然后将5a-f与气态氯化氢水解，得到相应的胺7a-（丁氧基羰基）-3-氨基-2 H -1-苯并吡喃-2-酮衍生物5a-f。f，最后在路易斯酸存在下，通过7a-f与亚氧化碳的反应制备10a-f。

  DOI：

  10.1002/jhet.5570350122

文献信息

• Synthesis and cytotoxicity study of novel 3-(triazolyl)coumarins based fluorescent scaffolds
  作者：Sohini Sinha、Anuja Plavuvalapil Kumaran、Debasish Mishra、Priyankar Paira

  DOI：10.1016/j.bmcl.2016.09.078

  日期：2016.11

  Recently a choice of fluorescent bioimaging probes have been developed as medical diagnostic tools. Herein, we have introduced a series of coumarin-based target specific probes for cancer theranostic application which play a dual role in the field of both diagnosis and therapy. A fluorogenic version of 1,3-dipolar cycloaddition between azides and alkynes (DBCO) has been introduced to develop the triazolylcoumarin

  最近，已开发出多种荧光生物成像探针作为医学诊断工具。本文中，我们介绍了一系列基于香豆素的靶标特异性探针，用于癌症治疗学应用，在诊断和治疗领域均起着双重作用。引入了叠氮化物和炔烃之间的1,3-偶极环加成的荧光形式（DBCO），以开发基于三唑基香豆素的荧光支架。筛选这些支架对乳腺癌（MCF7）和人上皮子宫颈癌（HeLa）细胞系的抗癌活性。已确定三唑基香豆素（5c和5d）在苯环中具有负电取代作用，在两种细胞系中均显示出最有效的抗癌作用。
• Simple and Efficient Copper(I)-Catalyzed Access to Three Versatile Aminocoumarin-Based Scaffolds using Isocyanoacetate
  作者：Tao Meng、Yiquan Zou、Oleg Khorev、Yu Jin、Huayong Zhou、Yongliang Zhang、Dingyu Hu、Lanping Ma、Xin Wang、Jingkang Shen

  DOI：10.1002/adsc.201000895

  日期：2011.4.18

  An efficient method has been developed for the one‐pot copper(I)‐catalyzed synthesis of 3‐aminocoumarin and its derivatives, such as 3‐substituted methylideneaminocoumarins and chromeno[3,4‐d]imidazol‐4(1H)‐ones. Significantly, the strategy presents a straightforward and efficient approach to constructing biologically useful molecular scaffolds.

  已开发出一种有效的方法，用于一锅铜（I）催化的3-氨基香豆素及其衍生物的合成，例如3-取代的亚甲基氨基香豆素和chromeno [3,4- d ]咪唑-4（1 H）-ones 。重要的是，该策略为构建生物学上有用的分子支架提供了一种简单有效的方法。
• Development of surface immobilized 3-azidocoumarin-based fluorogenic probe via strain promoted click chemistry
  作者：M. Vijaya Bharathi、Mohit Chhabra、Priyankar Paira

  DOI：10.1016/j.bmcl.2015.10.078

  日期：2015.12

  A new class of imaging probe, a fluorogenic version of 1, 3-dipolar cycloaddition of azides and alkynes has been developed. 3-azidocoumarin scaffolds were selectively immobilized on the DBCO modified bead surface via SPAAC and provide direct and strong fluorescence in fluorescence microscopy. This developed click-on beads could be applied to label various biomolecules, such as nucleic acids, proteins and other molecules. To this end, 5'(7-hydroxy 3-azido coumarin) labelled DNA primer also displayed strong fluorescence upon successful immobilization on the bead surface. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of new 2<i>H</i>,4<i>H</i>-benzopyrano[3,4-<i>b</i>]yridine-1,3,5-trione derivatives<i>via</i>carbon suboxide
  作者：Leonardo Bonsignore、Giuseppe Loy

  DOI：10.1002/jhet.5570350122

  日期：1998.1

  The new 2H,4H-[1]benzopyrano[3,4-b]pyridine-1,3,5-trione derivatives 10a-f were prepared in the following three steps: first the preparation of new N-(tert-butoxycarbonyl)-3-amino-2H-1-benzopyran-2-one derivatives 5a-f by reaction of coumarin-3-carboxylic acids and diphenylphosphorylazide, then hydrolysis of 5a-f with gaseous hydrogen chloride to give the corresponding amines 7a-f, and finally the

  新的2 ħ，4 ħ - [1]苯并吡喃并[3,4- b ]吡啶-1,3,5-三酮衍生物10A-F在以下三个步骤制备：新的第一制备ñ - （叔-通过香豆素-3-羧酸与二苯基磷酰叠氮化物的反应，然后将5a-f与气态氯化氢水解，得到相应的胺7a-（丁氧基羰基）-3-氨基-2 H -1-苯并吡喃-2-酮衍生物5a-f。f，最后在路易斯酸存在下，通过7a-f与亚氧化碳的反应制备10a-f。