4,5-dichloro-3,6-dihydroxy-10,10-dimethyl-10-sila-9H-xanthen-9-one | 1391714-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,5-dichloro-3,6-dihydroxy-10,10-dimethyl-10-sila-9H-xanthen-9-one
• 英文别名: 4,6-Dichloro-3,7-dihydroxy-5,5-dimethylbenzo[b][1]benzosilin-10-one；4,6-dichloro-3,7-dihydroxy-5,5-dimethylbenzo[b][1]benzosilin-10-one
• CAS: 1391714-50-3
• 化学式: C₁₅H₁₂Cl₂O₃Si
• 分子量: 339.25
• InChiKey: XSSSRRKTBRMPGD-UHFFFAOYSA-N

物化性质

• 沸点：
  459.7±45.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dichloro-3,6-dihydroxy-10,10-dimethyl-10-sila-9H-xanthen-9-one 在 咪唑 、 盐酸 、 水 、 仲丁基锂 、 1-羟基苯并三唑 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.16h， 生成 2-[2-[2-[2-[bis(carboxymethyl)amino]phenoxy]ethoxy]-N-(carboxymethyl)-4-[[4-(4,6-dichloro-7-hydroxy-5,5-dimethyl-3-oxobenzo[b][1]benzosilin-10-yl)-3-methylbenzoyl]amino]anilino]acetic acid
  参考文献：
  名称：

  红色荧光探针，用于监测细胞质钙离子的动力学

  摘要：

  我们看到红色（黄色和绿色）：探针1是为可视化细胞质Ca 2+而开发的，Ca 2+是许多生物学反应中的关键第二信使。新型探针适用于同时检测金属离子或蛋白质的多色成像，并且优于现有的红色荧光探针Rhod-2，可用于监测培养细胞的细胞质Ca 2+振荡（请参见具有1（顶部）和Rhod-2（底部））。

  DOI：

  10.1002/anie.201210279
• 作为产物：
  描述：

  间溴苯酚 在 咪唑 、 N-氯代丁二酰亚胺 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四丁基氟化铵 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 4,5-dichloro-3,6-dihydroxy-10,10-dimethyl-10-sila-9H-xanthen-9-one
  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

• FLUORESCENT PROBE
  申请人：Nagano Tetsuo

  公开号：US20130289256A1

  公开（公告）日：2013-10-31

  A compound represented by the formula (I) (R 1 represents hydrogen atom or a monovalent substituent; R 2 and R 3 represent hydrogen atom, an alkyl group, or a halogen atom; R 4 and R 5 represent an alkyl group or an aryl group; R 6 and R 7 represent hydrogen atom, an alkyl group, or a halogen atom; R 8 represent hydroxy group or a dialkoxyboranetriyl group; and X represents silicon atom, germanium atom, or tin atom), which is a novel fluorophore usable as a mother nucleus of an off/on type fluorescent probe not utilizing the intramolecular photoinduced electron transfer.

  由公式(I)表示的化合物（其中R1代表氢原子或单价取代基；R2和R3代表氢原子、烷基或卤素原子；R4和R5代表烷基或芳基；R6和R7代表氢原子、烷基或卤素原子；R8代表羟基或二烷氧基硼三基团；X代表硅原子、锗原子或锡原子），这是一种新型的荧光发光体，可用作不利用分子内光诱导电子转移的off/on型荧光探针的母核。
• Fluorescent probe
  申请人：Nagano Tetsuo

  公开号：US09170266B2

  公开（公告）日：2015-10-27

  A compound represented by the formula (I) (one of substituents represented by R1 is a trapping group for an object substance for measurement; R2 and R3 represent hydrogen, alkyl, or halogen; R4 and R5 represent alkyl or aryl; R6 and R7 represent hydrogen, alkyl, or halogen; R8 represents hydrogen, alkylcarbonyl, or alkylcarbonyloxymethyl, and X represents silicon, germanium, or tin, which can be used as a fluorescent probe that enables red color bioimaging using intramolecular photoinduced electron transfer.

  根据您提供的英文句子，翻译成中文如下： 由公式(I)表示的化合物（其中R1代表的一个取代基是对测量对象的捕捉基团；R2和R3代表氢、烷基或卤素；R4和R5代表烷基或芳基；R6和R7代表氢、烷基或卤素；R8代表氢、烷基羰基或烷基羰基氧甲基，而X代表硅、锗或锡），可作为荧光探针使用，利用分子内光诱导电子转移实现红色生物成像。
• Red Fluorescent Probe for Monitoring the Dynamics of Cytoplasmic Calcium Ions
  作者：Takahiro Egawa、Kazuhisa Hirabayashi、Yuichiro Koide、Chiaki Kobayashi、Naoya Takahashi、Tomoko Mineno、Takuya Terai、Tasuku Ueno、Toru Komatsu、Yuji Ikegaya、Norio Matsuki、Tetsuo Nagano、Kenjiro Hanaoka

  DOI：10.1002/anie.201210279

  日期：2013.4.2

  We see red (and yellow and green): Probe 1 was developed for the visualization of cytoplasmic Ca2+, a pivotal second messenger in many biological responses. The new probe is suitable for multicolor imaging for the simultaneous detection of metal ions or proteins and is superior to the existing red fluorescent probe Rhod‐2 for the monitoring of cytoplasmic Ca2+ oscillation in cultured cells (see fluorescence

  我们看到红色（黄色和绿色）：探针1是为可视化细胞质Ca 2+而开发的，Ca 2+是许多生物学反应中的关键第二信使。新型探针适用于同时检测金属离子或蛋白质的多色成像，并且优于现有的红色荧光探针Rhod-2，可用于监测培养细胞的细胞质Ca 2+振荡（请参见具有1（顶部）和Rhod-2（底部））。
• A Photoactivatable Formaldehyde Donor with Fluorescence Monitoring Reveals Threshold To Arrest Cell Migration
  作者：Lukas P. Smaga、Nicholas W. Pino、Gabriela E. Ibarra、Vishnu Krishnamurthy、Jefferson Chan

  DOI：10.1021/jacs.9b11899

  日期：2020.1.15

  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.