3-ethoxycarbonyl-7-iodocoumarin | 99969-90-1

• 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-ethoxycarbonyl-7-iodocoumarin
• 英文别名: 7-iodo-2-oxo-2H-chromene-3-carboxylic acid ethyl ester；7-Jod-2-oxo-2H-chromen-3-carbonsaeure-aethylester；Ethyl 7-iodo-2-oxochromene-3-carboxylate
• CAS: 99969-90-1
• 化学式: C₁₂H₉IO₄
• 分子量: 344.106
• InChiKey: CWJPHZKXHAXFKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  434.4±45.0 °C(Predicted)
• 密度：
  1.798±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-7-iodocoumarin 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Two-Photon Fluorescent Probes for Biological Mg²⁺ Detection Based on 7-Substituted Coumarin

  摘要：

  Two novel water-soluble coumarin-based compounds (OC7, NC7) were designed and synthesized as two-photon fluorescent probes for biological Mg2+ detection. The compounds feature a beta-keto, add as a high selective binding site for me and the coumarin framework as the two-photon fluorophore. OC7 and NC7 show significant "off-on" detecting signals (9.05-fold and 23.8-fold fluorescence enhancement) and lower detection limits compared with previous reported two-photon fluorescent probes for Mg2+. Moreover, OC7-Mg2+ and NC7-Mg2+ exhibit large two-photon absorption cross sections (340 and 615 GM) at the near-infrared wavelengths (740 and 860 nm), which indicates that the probes are very suitable for detection of Mg2+ in vivo. Both OC7 and NC7 are pH-insensitive and of low cytotoxicity and can be applied to image intracellular Mg2+ under two-photon microscopy (TPM). Our results provide a strategy to modify the coumarin fluorophore to get better two-photon fluorescent properties. And the results also suggest that electronic density of beta keto acid plays a very important role in the recognition of Mg2+.

  DOI：

  10.1021/jo502775t
• 作为产物：
  描述：

  7-aminocoumarin-3-carboxylic acid 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 生成 3-ethoxycarbonyl-7-iodocoumarin
  参考文献：
  名称：

  Kuwayama; Ichibagase, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 196

  摘要：

  DOI：

文献信息

• 一种七位取代的香豆素衍生物双光子荧光染料 及其制备方法
  申请人：安徽大学

  公开号：CN104119690B

  公开（公告）日：2016-06-29

  本发明公开了一种七位取代的香豆素衍生物双光子荧光染料，其结构通式为：其中R为CH3O-或(CH3)2N-。本发明制备的荧光染料合成简单而且得到了单晶结构，具有大的双光子吸收截面，可以被双光子激发产生荧光，具有低的细胞毒性，可以进入细胞，用于细胞生物成像。
• A two-photon fluorescent probe for real-time monitoring of autophagy by ultrasensitive detection of the change in lysosomal polarity
  作者：Jiacheng Jiang、Xiaohe Tian、Changzhi Xu、Shuxin Wang、Yan Feng、Man Chen、Haizhu Yu、Manzhou Zhu、Xiangming Meng

  DOI：10.1039/c7cc00752c

  日期：——

  The first two-photon probe, Lyso-OC, was proposed for use in monitoring cell autophagy by detection of the change in the lysosomal polarity during the membrane fusion process.

  第一个双光子探针Lyso-OC被提议用于通过检测溶酶体极性在膜融合过程中的变化来监测细胞自噬。
• A bright two-photon fluorescent probe for real-time monitoring autophagy in living cells
  作者：Chuankun Jiang、Longchun Li、Jiacheng Jiang、Lilin Hou、Gemin Fang、Yu Haizhu、Xiangming Meng

  DOI：10.1016/j.cclet.2019.07.046

  日期：2020.2

  Abstract A novel donor-acceptor (D-A) type of two-photon (TP) fluorescent probe, i.e. Lyso-OSC, based on the lysosome-targeting morpholine group was developed. The polarity sensing coumarin group was functionalized as the acceptor and the 1-vinyl-4-methoxybenzene group was engineered as the donor. The fluorescence intensity and emission maximum wavelength of Lyso-OSC are highly sensitive to the polarity

  摘要：以溶酶体为靶点的吗啉基团为基础，开发了一种新型的双光子（TP）荧光探针，即Lyso-OSC。极性感测香豆素基团被功能化为受体，而1-乙烯基-4-甲氧基苯基团被工程化为供体。Lyso-OSC的荧光强度和发射最大波长对溶剂的极性变化高度敏感。双光子吸收截面和组织穿透深度分别高达254 GM和150μm。强大的荧光，对极性的高敏感性，低细胞毒性和精确的溶酶体靶向能力使Lyso-OSC在检测细胞环境的极性变化方面具有出色的性能。为此，已经实现了活细胞的明亮，实时成像自噬。
• Deconstructive Insertion of Oximes into Coumarins: Modular Synthesis of Dihydrobenzofuran-Fused Pyridones
  作者：Ting-Yu Zheng、Yu-Qiang Zhou、Ning Yu、Yu-Lin Li、Tao Wei、Lan Peng、Yu Ling、Kun Jiang、Ye Wei

  DOI：10.1021/acs.orglett.2c00384

  日期：2022.4.1

  dihydrobenzofuran-fused pyridones in moderate to good yields with good functional group compatibility. The reaction likely involves a radical relay annulation, leading to the ring opening of the lactone moiety of the coumarins, and simultaneous formation of three new bonds. The investigation of photoluminescent properties reveals that several obtained compounds may have potential as fluorescent materials.

  在铜催化剂存在下，一系列肟解构插入香豆素中，以中等至良好的产率和良好的官能团相容性提供结构上有趣的二氢苯并呋喃稠合吡啶酮。该反应可能涉及自由基中继环化，导致香豆素的内酯部分开环，并同时形成三个新键。对光致发光特性的研究表明，几种获得的化合物可能具有作为荧光材料的潜力。
• Synthesis, bioactivity and molecular docking of novel coumarin-quinolinamide containing monocyclic monoterpenes as potential SDH inhibitors
  作者：Yuan Zhong、Cong Huang、Jing Zhang、Liang Zhong、Rong Zeng、Yuhuan Kuang、Xinyan Ye、Ziyin Xie、Ji Zhang、Zongde Wang、Shangxing Chen、Dayong Peng

  DOI：10.1016/j.molstruc.2024.138785

  日期：2024.11

  azoxystrobin. More importantly, the more bioactive compounds and did not affect the germination of cowpea seeds and also did not affect the growth of normal human hepatocytes and kidney cells. Molecular docking experiments showed that the introduction of the diethylamino group could promote the formation of hydrogen bonds between the hydrogen atom on the amide bond of the target compound and residue Tyr91, and

  琥珀酸脱氢酶抑制剂（SDHI）广泛用于植物抗真菌剂。为了打破耐药障碍，以天然樟脑或天然薄荷醇为先导化合物，设计合成了一系列含有单环单萜的新型香豆素-喹啉酰胺SDHI衍生物，并通过FT-IR、H NMR、C NMR和HRMS对其结构进行了表征。 。体外抗真菌活性测试结果表明，目标化合物对大多数植物病原真菌均具有抑制活性，特别是对 和 ，优于其他真菌。其中，化合物 和 比市售杀菌剂三环唑表现出更好的抑制效果，EC分别为16.90 mg/L和27.09 mg/L。在此基础上，采用离体叶试验进一步探讨化合物对植物体内水稻纹枯病的治疗和预防作用。体内抗真菌活性试验结果表明，化合物略优于阳性对照，与嘧菌酯的防治效果接近。更重要的是，这些更具生物活性的化合物并没有影响豇豆种子的发芽，也没有影响正常人体肝细胞和肾细胞的生长。分子对接实验表明，二乙氨基的引入可以促进目标化合物酰胺键上的氢原子与Tyr91残基