5-[1-(chloromethoxy)ethyl]-6-nitro-1,3-benzodioxole | 911377-03-2

• 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-(chloromethoxy)ethyl]-6-nitro-1,3-benzodioxole
• CAS: 911377-03-2
• 化学式: C₁₀H₁₀ClNO₅
• 分子量: 259.646
• InChiKey: VTXGOPMYMYAJCX-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±42.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[1-(chloromethoxy)ethyl]-6-nitro-1,3-benzodioxole 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.08h， 生成 methyl 3,4-(methylenedioxy)-6-nitrosophenyl ketone
  参考文献：
  名称：

  Optical Control of Small Molecule-Induced Protein Degradation

  摘要：

  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.

  DOI：

  10.1021/jacs.9b12718
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 sodium tetrahydroborate 、 磺酰氯 、 硝酸 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.33h， 生成 5-[1-(chloromethoxy)ethyl]-6-nitro-1,3-benzodioxole
  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

文献信息

• Caged nucleotides and oligonucleotides and their application
  申请人：——

  公开号：US08247540B2

  公开（公告）日：2012-08-21

  There is disclosed nucleotides and nucleotide analogs having a protecting or “caging” group. There is further disclosed oligonucleotides and oligonucleotides analogs formed having a protecting or “caging” group. There is further disclosed a method for decaging the nucleotides and nucleotide analogs having a protecting or “caging” group and oligonucleotides and oligonucleotide analogs having a caging group.

  披露了具有保护或“笼罩”基团的核苷酸和核苷酸类似物。进一步披露了形成具有保护或“笼罩”基团的寡核苷酸和寡核苷酸类似物。进一步披露了一种去笼罩具有保护或“笼罩”基团的核苷酸和核苷酸类似物以及具有笼罩基团的寡核苷酸和寡核苷酸类似物的方法。
• Photo-controlled cell-specific metabolic labeling of RNA
  作者：C. Feng、Y. Li、R. C. Spitale

  DOI：10.1039/c7ob01009e

  日期：——

  A method for photo-controlled cell-specific metabolic labeling is presented.

  一种用于光控细胞特异性代谢标记的方法被提出。
• Synthesis of Deoxypseudouridine 5′-Triphosphate Bearing the Photoremovable Protecting Group at the <i>N</i>1 Position Capable of Enzymatic Incorporation to DNA
  作者：Leo Takeshita、Yuji Yamada、Yoshiaki Masaki、Kohji Seio

  DOI：10.1021/acs.joc.9b02194

  日期：2020.2.21

  enzymatic incorporation of dNBΨTP and dNPOMΨTP using the Klenow fragment exo-. As a result, it was clarified that dNPOMΨTP could be incorporated to oligonucleotide 193 times more efficiently than dNBΨTP, as judged by Vmax/Km. We also performed the incorporation of at least eight dNPOMΨ residues in a 35-mer oligodeoxynucleotide. It has also been revealed that the oligodeoxynucleotides incorporating photocaged

  带有光可裂解保护基的脱氧核苷5'-三磷酸的酶促掺入是制备光笼化的寡脱氧核苷酸的有用方法。在这里，我们描述了新的光笼式脱氧核苷三磷酸酯N1-（2-硝基苄基）-脱氧pseudouridine三磷酸（dNBΨTP）和N1-（6-硝基胡椒基氧基甲基）-脱氧pseudouridine三磷酸（dNPOMΨTP）的合成。我们成功地合成了dNBΨTP和dNPOMΨTP，并将其应用于光笼寡核苷酸的酶促合成。另外，我们还合成了N1-（2-硝基苄基）-和N1-（6-硝基哌啶基氧基甲基）-脱氧伪杜鹃碱的亚磷酰胺，以使掺入它们的光笼寡核苷酸能够化学合成。通过在365nm下照射30秒和10s分别裂解寡核苷酸中的可光裂解的2-硝基苄基和6-硝基哌啶基氧基甲基。我们还研究了使用Klenow片段exo-酶促整合dNBΨTP和dNPOMΨTP的方法。结果表明，根据Vmax / Km判断，dNPOMΨTP可以比dNBΨTP高1
• 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。
• Npom-Protected NONOate Enables Light-Triggered NO/cGMP Signalling in Primary Vascular Smooth Muscle Cells
  作者：Anna S. Stroppel、Michael Paolillo、Thomas Ziegler、Robert Feil、Thorsten Stafforst

  DOI：10.1002/cbic.201700683

  日期：2018.6.18

  Spatiotemporally photocontrolled signal transduction: A new photoprotected NONOate, accessible in a small number of steps, was applied for light‐triggered cGMP induction in live primary mouse cells. The compound has excellent properties and opens new possibilities for spatiotemporal control in NO/cGMP studies.

  时空光控信号转导：将新的光保护性NONOate（可通过少量步骤访问）应用于活原代小鼠细胞中的光触发cGMP诱导。该化合物具有出色的性能，为NO / cGMP研究中的时空控制开辟了新的可能性。