5-(1-((methylthio)methoxy)ethyl)-6-nitrobenzo[d][1,3]dioxole | 911377-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(1-((methylthio)methoxy)ethyl)-6-nitrobenzo[d][1,3]dioxole
• 英文别名: 5-[1-[(methylthio)methoxy]ethyl]-6-nitro-1,3-benzodioxole；5-[1-(Methylsulfanylmethoxy)ethyl]-6-nitro-1,3-benzodioxole
• CAS: 911377-02-1
• 化学式: C₁₁H₁₃NO₅S
• 分子量: 271.294
• InChiKey: DKVWTCCBVWKUSR-UHFFFAOYSA-N

物化性质

• 沸点：
  394.7±42.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(1-((methylthio)methoxy)ethyl)-6-nitrobenzo[d][1,3]dioxole 在 磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  A Photoactivatable Formaldehyde Donor with Fluorescence Monitoring Reveals Threshold To Arrest Cell Migration

  摘要：

  Controlled light-mediated delivery of biological analytes can enable the investigation of highly reactivity molecules within living systems. As many biological effects are concentration dependent, it is critical to determine the location, time, and quantity of analyte donation. In this work, we have developed the first photoactivatable donor for formaldehyde (FA). Our optimized photoactivatable donor, photoFAD-3, is equipped with a fluorescence readout that enables monitoring of FA release with a concomitant 139-fold fluorescence enhancement. Tuning of photostability and cellular retention enabled quantification of intracellular FA release through cell lysate calibration. Application of photoFAD-3 uncovered the concentration range necessary for arresting wound healing in live cells. This marks the first report where a photoactivatable donor for any analyte has been used to quantify intracellular release.

  DOI：

  10.1021/jacs.9b11899
• 作为产物：
  描述：

  6-硝基胡椒醛 在 三甲基铝 、 过氧化苯甲酰 作用下， 以 正庚烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 5-(1-((methylthio)methoxy)ethyl)-6-nitrobenzo[d][1,3]dioxole
  参考文献：
  名称：

  Photo-controlled cell-specific metabolic labeling of RNA

  摘要：

  一种用于光控细胞特异性代谢标记的方法被提出。

  DOI：

  10.1039/c7ob01009e

文献信息

• A New Photocaging Group for Aromatic <i>N</i>-Heterocycles
  作者：Alexander Deiters、Hrvoje Lusic

  DOI：10.1055/s-2006-942424

  日期：2006.7

  Biologically relevant nitrogen-containing heterocycles were photo-protected using an NPOM caging group that is stable under physiological conditions but readily decages under irradiation with non-photodamaging UV light.

  生物相关的含氮杂环化合物采用NPOM保护基团进行光保护，该基团在生理条件下稳定，但在非光损伤的紫外光照射下易于去除保护。
• Protocols for the generation of caged guideRNAs for light-triggered RNA-targeting with SNAP-ADARs
  作者：Alfred Hanswillemenke、Thorsten Stafforst

  DOI：10.1016/bs.mie.2019.06.004

  日期：——
• Optical Control of Small Molecule-Induced Protein Degradation
  作者：Yuta Naro、Kristie Darrah、Alexander Deiters

  DOI：10.1021/jacs.9b12718

  日期：2020.2.5

  As an emerging approach to protein perturbation, small molecule-induced protein degradation has gained significant attention as both a chemical tool and a potential therapeutic. To enable discrete control over its function, we have developed a broadly applicable approach for the optical activation of small molecule-induced protein degradation. By installing two different photolabile protecting groups, so-called caging groups, onto two different ligands recruiting Von Hippel-Lindau (VHL) and cereblon (CRBN) E3 ubiquitin ligases, our strategy enables light-triggered protein degradation for any small molecule warhead.