3-(diethylmalonate-1H)-5-chloro-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)

• 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: 3-(diethylmalonate-1H)-5-chloro-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)
• 英文别名: 4,4-difluoro-8-(4-tolyl)-3-diethyl propanedioate-5-chloro-4-bora-3a,4a-diaza-s-indacene；3-(diethylmalonate-1H)-5-chloro-BODIPY；Diethyl 2-[12-chloro-2,2-difluoro-8-(4-methylphenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-4-yl]propanedioate；diethyl 2-[12-chloro-2,2-difluoro-8-(4-methylphenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-4-yl]propanedioate
• 化学式: C₂₃H₂₂BClF₂N₂O₄
• 分子量: 474.699
• InChiKey: CGRQHWRQMYFZMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(diethylmalonate-1H)-5-chloro-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) 、 DL-半胱氨酸 以 aq. buffer 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine

  摘要：

  We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.

  DOI：

  10.1021/ja309079f
• 作为产物：
  描述：

  3,5-dichloro-8-(4-tolyl) BODIPY 、 丙二酸二乙酯 在 sodium hydride 作用下， 以 乙腈 为溶剂， 以67%的产率得到3-(diethylmalonate-1H)-5-chloro-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)
  参考文献：
  名称：

  Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution

  摘要：

  BODIPY色基可以通过对3,5-二氯BODIPY进行O-、N-、S-和C-亲核试剂的单取代或双取代进行简单修改。新BODIPY衍生物的吸收和荧光光谱数据也被报道。

  DOI：

  10.1039/b512756d

文献信息

• Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution
  作者：Taoufik Rohand、Mukulesh Baruah、Wenwu Qin、Noël Boens、Wim Dehaen

  DOI：10.1039/b512756d

  日期：——

  The BODIPY chromophore can be easily modified by nucleophilic mono- or disubstitution of 3,5-dichloroBODIPY with O-, N-, S- and C-nucleophiles. Absorption and fluorescence spectral data of the new BODIPY derivatives are also reported.

  BODIPY色基可以通过对3,5-二氯BODIPY进行O-、N-、S-和C-亲核试剂的单取代或双取代进行简单修改。新BODIPY衍生物的吸收和荧光光谱数据也被报道。
• Solvent-dependent photophysical properties of borondipyrromethene dyes in solution
  作者：Wenwu Qin、Taoufik Rohand、Mukulesh Baruah、Alina Stefan、Mark Van der Auweraer、Wim Dehaen、Noël Boens

  DOI：10.1016/j.cplett.2005.12.098

  日期：2006.3

  Four fluorescent dyes derived from 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) with unusual substituents (chloro, methoxy, and malonate) at the 3,5-positions have been synthesized by a novel nucleophilic substitution reaction of 3,5-dichloroBODIPY. Their solvent-dependent photophysical properties have been investigated by means of UV/Vis absorption, steady-state and time-resolved fluorimetry. For each compound, the fluorescence quantum yield and lifetime are lower in solvents with higher polarity due to an increase in the rate of nonradiative deactivation. The fluorescence rate constants are in the (1.6-2.0) x 10(8) s(-1) range. The borondipyrro-methene derivatives show small Stokes shifts (between 440 and 490 cm(-1)) and narrow absorption (FWHM between 710 and 820 cm(-1)) and emission bands. (c) 2006 Elsevier B.V. All rights reserved.
• BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine
  作者：Li-Ya Niu、Ying-Shi Guan、Yu-Zhe Chen、Li-Zhu Wu、Chen-Ho Tung、Qing-Zheng Yang

  DOI：10.1021/ja309079f

  日期：2012.11.21

  We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.