4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzaldehyde | 160888-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzaldehyde
• 英文别名: Ethyl 2-[2-(2-ethoxy-2-oxoethoxy)-5-formyl-4-nitrophenoxy]acetate
• CAS: 160888-74-4
• 化学式: C₁₅H₁₇NO₉
• 分子量: 355.301
• InChiKey: OJIDMPKZAXVJHM-UHFFFAOYSA-N

物化性质

• 沸点：
  513.529±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.331±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzaldehyde 在 sodium tetrahydroborate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzyl alcohol methanesulfonate
  参考文献：
  名称：

  Photochemical Gating of Intracellular Ca²⁺ Release Channels

  摘要：

  We have synthesized BiNiX, a caged methylxanthine agonist for the ryanodine receptor (RyR)the major calcium channel that mediates Ca2+ release from intracellular Ca2+ stores in electrically excitable cells. BiNiX is easily loaded into living cells through incubation with its acetoxymethyl (AM) ester. Delivery of focused UV light pulses to the loaded cell releases paraxanthine focally and rapidly to activate RyRs to release Ca2+, thus elevating intracellular Ca2+ concentration to initiate Ca2+-dependent signaling cascades. We demonstrate the biological utility of BiNiX in heart muscle cells by showing that local intracellular photolysis of BiNiX triggers Ca2+ release and consequent muscle contraction.

  DOI：

  10.1021/ja069361q
• 作为产物：
  描述：

  3,4-dicarboethoxymethyleneoxybenzaldehyde 在 potassium nitrate 、 三氟乙酸 作用下， 反应 16.0h， 以86%的产率得到4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzaldehyde
  参考文献：
  名称：

  Photochemical Gating of Intracellular Ca²⁺ Release Channels

  摘要：

  We have synthesized BiNiX, a caged methylxanthine agonist for the ryanodine receptor (RyR)the major calcium channel that mediates Ca2+ release from intracellular Ca2+ stores in electrically excitable cells. BiNiX is easily loaded into living cells through incubation with its acetoxymethyl (AM) ester. Delivery of focused UV light pulses to the loaded cell releases paraxanthine focally and rapidly to activate RyRs to release Ca2+, thus elevating intracellular Ca2+ concentration to initiate Ca2+-dependent signaling cascades. We demonstrate the biological utility of BiNiX in heart muscle cells by showing that local intracellular photolysis of BiNiX triggers Ca2+ release and consequent muscle contraction.

  DOI：

  10.1021/ja069361q

文献信息

• Optochemical Control of Bacterial Gene Expression: Novel Photocaged Compounds for Different Promoter Systems
  作者：Fabian Hogenkamp、Fabienne Hilgers、Nora Lisa Bitzenhofer、Vera Ophoven、Mona Haase、Claus Bier、Dennis Binder、Karl‐Erich Jaeger、Thomas Drepper、Jörg Pietruszka

  DOI：10.1002/cbic.202100467

  日期：2022.1.5

  Novel optochemical tools for controlling gene expression in E. coli were investigated. Six photocaged carbohydrates with redshifted absorption and a photocaged salicylic acid derivative were synthesized, photochemically characterized and applied in vivo for light-mediated target gene expression. The potential challenges during the establishment of a new optochemically controllable system and sufficient

  研究了用于控制大肠杆菌基因表达的新型光化学工具。合成了六种具有红移吸收的光笼碳水化合物和光笼水杨酸衍生物，进行光化学表征并应用于体内光介导的靶基因表达。详细讨论了建立新的光化学可控系统过程中的潜在挑战和足够的解决方案。
• Effect of Photocaged Isopropyl β‐ <scp>d</scp> ‐1‐thiogalactopyranoside Solubility on the Light Responsiveness of LacI‐controlled Expression Systems in Different Bacteria
  作者：Fabian Hogenkamp、Fabienne Hilgers、Andreas Knapp、Oliver Klaus、Claus Bier、Dennis Binder、Karl‐Erich Jaeger、Thomas Drepper、Jörg Pietruszka

  DOI：10.1002/cbic.202000377

  日期：2021.2.2

  Extended toolbox: New photocaged IPTG derivatives with various hydrophobicities for light‐induced gene expression were synthesised and tested with three different expression host strains. The most water‐soluble compound showed superior performance, especially in Bacillus subtilis.

  扩展工具箱：合成了具有各种疏水性的新型光笼 IPTG 衍生物，用于光诱导基因表达，并用三种不同的表达宿主菌株进行测试。水溶性最强的化合物表现出优越的性能，尤其是在枯草芽孢杆菌中。
• Photochemical Gating of Intracellular Ca²⁺ Release Channels
  作者：Jiahong Ni、Darryl A. Auston、David A. Freilich、Sukumaran Muralidharan、Eric A. Sobie、Joseph P. Y. Kao

  DOI：10.1021/ja069361q

  日期：2007.5.1

  We have synthesized BiNiX, a caged methylxanthine agonist for the ryanodine receptor (RyR)the major calcium channel that mediates Ca2+ release from intracellular Ca2+ stores in electrically excitable cells. BiNiX is easily loaded into living cells through incubation with its acetoxymethyl (AM) ester. Delivery of focused UV light pulses to the loaded cell releases paraxanthine focally and rapidly to activate RyRs to release Ca2+, thus elevating intracellular Ca2+ concentration to initiate Ca2+-dependent signaling cascades. We demonstrate the biological utility of BiNiX in heart muscle cells by showing that local intracellular photolysis of BiNiX triggers Ca2+ release and consequent muscle contraction.