2,3,4-tricarbomethoxy-α-pyrone | 151797-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,3,4-tricarbomethoxy-α-pyrone
• 英文别名: 2,3,4-Tricarbomethoxy-2-pyrone；trimethyl 2-oxo-2H-pyran-4,5,6-tricarboxylate；Trimethyl 6-oxopyran-2,3,4-tricarboxylate
• CAS: 151797-12-5
• 化学式: C₁₁H₁₀O₈
• 分子量: 270.196
• InChiKey: NQHJZJXXLQGTLK-UHFFFAOYSA-N

物化性质

• 沸点：
  367.8±42.0 °C(predicted)
• 密度：
  1.441±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tricarbomethoxy-α-pyrone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 2,3,4-Tricarbomethoxy-4-hydroxypentanoic acid lactone
  参考文献：
  名称：

  Hydration of alkynes in anhydrous medium with formic acid as water donor

  摘要：

  Formic acid has been found to hydrate alkynes in the absence of water to give oxo products and carbon monoxide. The scope of the reaction of alkynes and formic acid has been delineated. Hydrocarbon alkynes were found to be reactive in the absence of catalyst. Functionalized alkynes, in particular oxygenated alkynes, are inert toward formic acid but can be activated catalytically with Ru3(CO)12. Consequently, all the tested types of alkynes were found to give oxo products and CO with formic acid. The mechanism of the reaction was examined. With some alkynes, the primary oxo products underwent secondary reactions that gave rise to unexpected products.

  DOI：

  10.1021/jo00078a023
• 作为产物：
  描述：

  溶剂黄146 、 丁炔二酸二甲酯 在 十二羰基三钌 作用下， 反应 0.75h， 以50%的产率得到2,3,4-tricarbomethoxy-α-pyrone
  参考文献：
  名称：

  Menashe, Naim; Shvo, Youval, Heterocycles, 1993, vol. 35, # 2, p. 611 - 613

  摘要：

  DOI：

文献信息

• Pyranthiones/Pyrones: “Click and Release” Donors for Subcellular Hydrogen Sulfide Delivery and Labeling**
  作者：Wei Huang、Nipuni Gunawardhana、Yunlei Zhang、Jorge Escorihuela、Scott T. Laughlin

  DOI：10.1002/chem.202303465

  日期：2024.2

  Hydrogen sulfide (H₂S), one of the most important gasotransmitters, plays a critical role in endogenous signaling pathways of many diseases. However, developing H₂S donors with both tunable release kinetics and high release efficiency for subcellular delivery has been challenging. Here, we describe a click and release reaction between pyrone/pyranthiones and bicyclononyne (BCN). This reaction features a release of CO₂/COS with second‐order rate constants comparable to Strain‐Promoted Azide‐Alkyne Cycloaddition reactions (SPAACs). Interestingly, pyranthiones showed enhanced reaction rates compared to their pyrone counterparts. We investigated pyrone biorthogonality and demonstrated their utility in protein labeling applications. Moreover, we synthesized substituted pyranthiones with H₂S release kinetics that can address the range of physiologically relevant H₂S dynamics in cells and achieved quantitative H₂S release efficiency in vitro. Finally, we explored the potential of pyranthiones as H₂S/COS donors for mitochondrial‐targeted H₂S delivery in living cells.

  摘要硫化氢（H2S）是最重要的气体递质之一，在许多疾病的内源性信号通路中发挥着关键作用。然而，开发具有可调释放动力学和高释放效率的亚细胞递送硫化氢供体一直是一项挑战。在这里，我们描述了吡喃酮/吡喃硫醚与双环壬炔（BCN）之间的点击释放反应。该反应的特点是释放 CO2/COS，其二阶速率常数与应变促进叠氮-炔环加成反应（SPAACs）相当。有趣的是，与吡喃酮类化合物相比，吡喃硫醚类化合物的反应速率更高。我们研究了吡喃酮的生物配位性，并证明了它们在蛋白质标记应用中的实用性。此外，我们还合成了具有 H2S 释放动力学的取代吡喃硫酮，其释放动力学可应对细胞中与生理相关的 H2S 动态范围，并实现了体外定量 H2S 释放效率。最后，我们探索了吡喃硫醚作为 H2S/COS 给体在活细胞中进行线粒体靶向 H2S 释放的潜力。
• Menashe Naim, Shvo Youval, J. Org. Chem, 58 (1993) N 26, S 7434-7439
  作者：Menashe Naim, Shvo Youval

  DOI：——

  日期：——
• Hydration of alkynes in anhydrous medium with formic acid as water donor
  作者：Naim Menashe、Youval Shvo

  DOI：10.1021/jo00078a023

  日期：1993.12

  Formic acid has been found to hydrate alkynes in the absence of water to give oxo products and carbon monoxide. The scope of the reaction of alkynes and formic acid has been delineated. Hydrocarbon alkynes were found to be reactive in the absence of catalyst. Functionalized alkynes, in particular oxygenated alkynes, are inert toward formic acid but can be activated catalytically with Ru3(CO)12. Consequently, all the tested types of alkynes were found to give oxo products and CO with formic acid. The mechanism of the reaction was examined. With some alkynes, the primary oxo products underwent secondary reactions that gave rise to unexpected products.
• Menashe, Naim; Shvo, Youval, Heterocycles, 1993, vol. 35, # 2, p. 611 - 613
  作者：Menashe, Naim、Shvo, Youval

  DOI：——

  日期：——