3',6'-二(二乙基氨基)-2-苯基螺[异吲哚-3,9'-氧杂蒽]-1-酮 | 38660-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3',6'-二(二乙基氨基)-2-苯基螺[异吲哚-3,9'-氧杂蒽]-1-酮
• 英文名称: 3',6'-bis(diethylamino)-2-phenylspiro<1H-isoindole-1,9'(9H)xanthene>-3(2H)-one
• 英文别名: 3',6'-bis(diethylamino)-2-phenyl-2,3-dihydrospiro[isoindole-1,9'-xanthene]-3-one；3',6'-bis(diethylamino)-2-phenylspiro[isoindoline-1,9'-xanthen]-3-one；3',6'-bis-diethylamino-2-phenyl-spiro[isoindole-1,9'-xanthen]-3-one；3',6'-Bis-diaethylamino-2-phenyl-spiro[isoindolin-1,9'-xanthen]-3-on；3',6'-bis(diethylamino)-2-phenylspiro(1H-isoindole-1,9'-[9H]xanthene)-3(2H)-one；Spiro[1H-isoindole-1,9'-[9H]xanthen]-3(2H)-one, 3',6'-bis(diethylamino)-2-phenyl-；3',6'-bis(diethylamino)-2-phenylspiro[isoindole-3,9'-xanthene]-1-one
• CAS: 38660-35-4
• 化学式: C₃₄H₃₅N₃O₂
• mdl: MFCD00182788
• 分子量: 517.671
• InChiKey: IMYNRKANUSOMGU-UHFFFAOYSA-N

物化性质

• 沸点：
  691.5±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3',6'-二(二乙基氨基)-2-苯基螺[异吲哚-3,9'-氧杂蒽]-1-酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以72%的产率得到3'-N,3'-N,6'-N,6'-N-tetraethyl-2-phenyl-2,3-dihydrospiro-[isoindole-1,9'-xanthene]-3',6'-diamine
  参考文献：
  名称：

  Anilinomethylrhodamines: pH Sensitive Probes with Tunable Photophysical Properties by Substituent Effect

  摘要：

  A series of pH dependent rhodamine analogues possessing an anilino-methyl moiety was developed and shown to exhibit a unique photophysical response to pH. These anilinomethylrhodamines (AnMR) maintain a colorless, non-fluorescent spirocyclic structure at high pH. The spirocyclic structures open in mildly acidic conditions and are weakly fluorescent; however, at very low pH, the fluorescence is greatly enhanced. The equilibrium constants of these processes show a linear response to substituent effects, which was demonstrated by the Hammett equation.

  DOI：

  10.1021/jo401323g
• 作为产物：
  描述：

  罗丹明B 在 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成 3',6'-二(二乙基氨基)-2-苯基螺[异吲哚-3,9'-氧杂蒽]-1-酮
  参考文献：
  名称：

  The utilization of pH sensitive spirocyclic rhodamine dyes for monitoring D-fructose consumption during a fermentation process

  摘要：

  通过使用由芳基硼酸作为主分子和 pH 敏感的螺环罗丹明染料作为指示分子组成的双组分传感系统，实现了对 D-果糖的比色和荧光检测。

  DOI：

  10.1039/c3nj00613a

文献信息

• A Multisite-Binding Switchable Fluorescent Probe for Monitoring Mitochondrial ATP Level Fluctuation in Live Cells
  作者：Lu Wang、Lin Yuan、Xian Zeng、Juanjuan Peng、Yong Ni、Jun Cheng Er、Wang Xu、Bikram Keshari Agrawalla、Dongdong Su、Beomsue Kim、Young-Tae Chang

  DOI：10.1002/anie.201510003

  日期：2016.1.26

  triphosphate (ATP), commonly produced in mitochondria, is required by almost all the living organisms; thus fluorescent probes for monitoring mitochondrial ATP levels fluctuation are essential and highly desired. Herein, we report a multisite‐binding switchable fluorescent probe, ATP‐Red 1, which selectively and rapidly responds to intracellular concentrations of ATP. Live‐cell imaging indicated that ATP‐Red 1

  线粒体中通常产生的三磷酸腺苷（ATP）是几乎所有活生物体都需要的。因此，用于监测线粒体ATP水平波动的荧光探针是必不可少的。在本文中，我们报告了一种多位点结合可转换的荧光探针ATP-Red 1，该探针 对细胞内的ATP浓度具有选择性和快速反应。活细胞成像表明，ATP-Red  1主要定位于线粒体，具有良好的生物相容性和膜渗透性。特别是在ATP‐Red 1的帮助下 ，我们成功地观察到不仅在KCN存在和饥饿状态下线粒体ATP水平降低，而且在细胞凋亡的早期阶段也观察到线粒体ATP水平升高。这些结果表明，ATP-Red  1是研究ATP相关生物过程的有用工具。
• Tuning the Photophysical Properties of Spirolactam Rhodamine Photoswitches
  作者：Bo Li、Uroob Haris、Maha Aljowni、Andrew Nakatsuka、Shreya K. Patel、Alexander R. Lippert

  DOI：10.1002/ijch.202000083

  日期：2021.3

  Spirolactam rhodamines are fluorescent photoswitches that are useful for single molecule localization microscopy, volumetric 3D digital light photoactivatable dye displays, and other applications. Measurement of the photophysical properties, particularly photoswitching kinetics and quantum yields, is challenging and a comprehensive understanding of how molecular structure affects these parameters remains

  螺内酰胺若丹明是荧光光电开关，可用于单分子定位显微镜，体积3D数字光可光活化染料显示器和其他应用。光物理性质，特别是光开关动力学和量子产率的测量是具有挑战性的，并且对分子结构如何影响这些参数的全面理解仍然不完整。在这项研究中，我们合成了一系列N‐芳基螺内酰胺若丹明光敏开关，在585 nm和518 nm处发出荧光。光开关的荧光形式的消光系数和荧光量子产率已使用过量的三氟乙酸驱动平衡达到开放形式进行了测量。通过监测动力学以达到开态和关态之间的平衡并将此数据拟合到平衡中的反应速率方程，从而开发了一种确定光开关动力学和量子产率的方法。评价了基于芳基取代基的电子和空间特性的趋势。利用此信息，使用绿色（518 nm）发射的光电开关完成了3D体素形成的原理证明，从而为多色体积3D显示器奠定了基础。
• Long‐Lived Charge‐Transfer State Induced by Spin‐Orbit Charge Transfer Intersystem Crossing (SOCT‐ISC) in a Compact Spiro Electron Donor/Acceptor Dyad
  作者：Dongyi Liu、Ahmed M. El‐Zohry、Maria Taddei、Clemens Matt、Laura Bussotti、Zhijia Wang、Jianzhang Zhao、Omar F. Mohammed、Mariangela Di Donato、Stefan Weber

  DOI：10.1002/anie.202003560

  日期：2020.7.6

  3CT state (0.94 μs in deaerated n‐hexane) with high energy level (ca. 2.12 eV). The cascade photophysical processes of the dyad upon photoexcitation are summarized as 1NI*→1CT→3NI*→3CT. With time‐resolved electron paramagnetic resonance (TREPR) spectra, an EEEAAA electron‐spin polarization pattern was observed for the naphthalimide‐localized triplet state. Our spiro compact dyad structure and the electron

  我们制备了概念上新颖的，完全刚性的螺线致密电子供体（若丹明B，内酰胺形式，RB）/受体（萘二甲酰亚胺； NI）正交二元组，以基于电子实现长寿命的三重态电荷转移（3 CT）状态使用自旋轨道电荷转移系统间交叉（SOCT-ISC）进行自旋控制。瞬态吸收（TA）光谱表明，第一次电荷分离（CS）发生在2.5 ps之内，随后的SOCT-ISC则需要8 ns才能产生3 NI *状态。然后，缓慢的二次CS（125 ns）给出了具有高能级（约2.12 eV）的长寿命3 CT状态（在脱气的正己烷中为0.94μs）。激发后双级联的级联光物理过程概括为1 NI *→ 1 CT→3 NI *→ 3 CT。利用时间分辨电子顺磁共振（TREPR）光谱，观察到了萘二酰亚胺局部三重态的EEEAAA电子自旋极化图。我们的螺致密双晶结构和电子自旋控制方法与以前的方法不同，以前的方法必须调用具有固有ISC能力的过渡金属配位体或生色团。
• Substituent effects on the turn-on kinetics of rhodamine-based fluorescent pH probes
  作者：William L. Czaplyski、Grace E. Purnell、Courtney A. Roberts、Rebecca M. Allred、Elizabeth J. Harbron

  DOI：10.1039/c3ob42089b

  日期：——

  Fluorescent turn-on probes based on a rhodamine spirolactam (RSL) structure have recently become a popular means of detecting pH, metal ions, and other analytes of interest. RSLs are colorless and non-fluorescent until the target analyte induces opening of the spirocyclic ring system, revealing the fully conjugated and highly fluorescent rhodamine dye. Among RSLs opened by acid, we have observed wide variation in the kinetics of the fluorescence turn-on process such that some probes would not be usable in situations where a rapid reading is desired or the pH fluctuates temporally. Herein we present a systematic investigation of the fluorescence turn-on kinetics of RSLs to probe the hypothesis that the reaction rates are influenced by the electronic properties of the spirolactam ring system. A series of 8 aniline-derived RSLs with para substituents ranging from electron-donating to electron-withdrawing was prepared from rhodamine B. The fluorescence turn-on rates are observed to increase by a factor of four as the substituent is tuned from methoxy to nitro. This effect is explained in terms of the destabilization of the reaction intermediate by the substituent. As the reaction rates increase across the series, a concomitant increase in fluorescence intensity is also observed. This result is attributed to an increase in the concentration of the fluorescent form of the dye and is consistent with the expected equilibrium properties of this system. These findings are applied to the design of a faster-reacting and more intensely fluorescent RSL pH probe.

  基于罗丹明螺内酰胺（RSL）结构的荧光开启探针近来已成为检测 pH 值、金属离子和其他相关分析物的常用方法。RSL 是无色无荧光的，直到目标分析物诱导螺环系统打开，露出完全共轭的高荧光罗丹明染料。在被酸打开的 RSL 中，我们观察到荧光开启过程的动力学差异很大，因此有些探针在需要快速读数或 pH 值随时间波动的情况下无法使用。在此，我们对 RSL 的荧光开启动力学进行了系统研究，以探索反应速率受螺内酰胺环系统电子特性影响的假设。研究人员利用罗丹明 B 制备了一系列 8 种苯胺衍生的 RSL，这些 RSL 的对位取代基的范围从给电子到抽电子不等。这种效应的原因是取代基破坏了反应中间体的稳定性。随着各系列反应速率的增加，荧光强度也随之增加。这一结果归因于染料荧光形式浓度的增加，并与该体系的预期平衡特性相一致。这些发现被应用于设计反应更快、荧光更强的 RSL pH 探针。
• Study of Rhodamine‐Based Fluorescent Probes for Organic Radical Intermediates
  作者：Jiaxin He、Boyu Yan、Jiangtao Meng、Maogang Ran、Yutong Zhou、Jinfei Deng、Chao‐Jun Li、Qiuli Yao

  DOI：10.1002/ejoc.202100299

  日期：2021.8.6

  Rhodamine-based amide derivatives were used as fluorescent probes in the detection and real-time monitoring of radical intermediates in different solvents. Mechanism studies reveal a reversible opening and closing of the spirolactam ring with the presence or absence of radicals.

  基于罗丹明的酰胺衍生物被用作荧光探针，用于检测和实时监测不同溶剂中的自由基中间体。机理研究揭示了在存在或不存在自由基的情况下螺内酰胺环的可逆打开和关闭。