6-(tert-butyl)-1',3',3'-trimethylspiro[chromene-2,2'-indoline]-8-carbaldehyde | 1370284-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-(tert-butyl)-1',3',3'-trimethylspiro[chromene-2,2'-indoline]-8-carbaldehyde
• 英文别名: 6-(tert-butyl)-1′,3′,3′-trimethylspiro[chromene-2,2′-indoline]-8-carbaldehyde；6-tert-butyl-1',3',3'-trimethylspiro[chromene-2,2'-indole]-8-carbaldehyde；6-Tert-butyl-1',3',3'-trimethylspiro[chromene-2,2'-indole]-8-carbaldehyde
• CAS: 1370284-34-6
• 化学式: C₂₄H₂₇NO₂
• 分子量: 361.484
• InChiKey: WXXZRUZHQJTOCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(tert-butyl)-1',3',3'-trimethylspiro[chromene-2,2'-indoline]-8-carbaldehyde 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 1′,3′,3′-trimethyl-3-[(E)-2-(1′′,3′',3′′-trimethyl-3H-indole-2′′-yl)vinyl]-6-(tert-butyl)-8-[(E)-4-flluorobenzoylhydrozino-(1-ylmethylene)]spiro[2H-1-benzopyran-2,2′-indoline]
  参考文献：
  名称：

  A spiropyran-acylhydrazone dyad: Uncovering another way of cleaving the Cspiro-O bond of the classical photochromic molecule

  摘要：

  Spiropyran, as famous molecular sensor, can transform from its closed forms into the corresponding opened merocyanine through C-spiro-O bond cleavage when an analyte attacks the spirocarbon or oxygen atom in the spiropyran. Herein, a spiropyran-acylhydrazone dyad 4 is synthesized followed by spiropyran-like 5 and nonspiropyran diacylhydrazone 6 obtained simultaneously, and its reactivity to nucleophiles is investigated. Thus a third attacking position, located at the carbon atom opposite to the oxygen connected to C-spiro, is found, which involves C-spiro-O bond cleavage and recombination. Consequently, a nucleophilic addition mechanism in spiropyran is proposed. 4 and 5 both can discriminate Mg2+ from Ca2+ with different response time and sensitivity, while non-spiropyran 6 does not respond to the two metal ions. This work not only discovers an outstanding sensor for discriminating Mg2+ from Ca2+, but also provides new insight for transforming and modifying spiropyrans.

  DOI：

  10.1016/j.dyepig.2020.108805
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 哌啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 6-(tert-butyl)-1',3',3'-trimethylspiro[chromene-2,2'-indoline]-8-carbaldehyde
  参考文献：
  名称：

  A highly selective and reversible fluorescent Cu²⁺and S²⁻probe under physiological conditions and in live cells

  摘要：

  已合成一种新的含螺环癸啉衍生物RB-SP2，并应用于检测Cu2+和S2−。RB-SP2随后被用作成像探针，用于在生理pH下检测这些离子在HeLa细胞中的存在。

  DOI：

  10.1039/c4ra03916e

文献信息

• Control of Imine Exchange Kinetics with Photoswitches to Modulate Self-Healing in Polysiloxane Networks by Light Illumination
  作者：Michael Kathan、Petr Kovaříček、Christoph Jurissek、Antti Senf、Andre Dallmann、Andreas F. Thünemann、Stefan Hecht

  DOI：10.1002/anie.201605311

  日期：2016.10.24

  Various aldehyde‐containing photoswitches have been developed whose reactivity toward amines can be controlled externally. A thermally stable bifunctional diarylethene, which in its ring‐closed form exhibits imine formation accelerated by one order of magnitude, was used as a photoswitchable crosslinker and mixed with a commercially available amino‐functionalized polysiloxane to yield a rubbery material

  已经开发了各种含醛的光开关，它们对胺的反应性可以在外部控制。一种热稳定的双功能二芳基二芳基乙烯，以其闭环形式表现出亚胺形成速度提高一个数量级，被用作光开关交联剂，并与市售的氨基官能化聚硅氧烷混合，得到具有粘弹性和自修复性的橡胶状材料可以通过辐照可逆地调整的特性。
• pH比率型荧光探针SP-DCCH的制备方法及 生物成像应用
  申请人：温州医科大学

  公开号：CN111518107B

  公开（公告）日：2021-03-09

  本发明公开了一种pH比率型荧光探针SP‑DCCH的制备方法及生物成像应用，用于酸性以及弱碱条件下与生物成像，通过检测该探针在不同pH缓冲液(1.68～7.21)中的荧光光谱，可以看出随着pH值的降低，pH比率型荧光探针在λ＝525nm处的荧光强度逐渐降低，在λ＝629nm处的荧光强度逐渐升高，说明pH比率型荧光探针对pH非常敏感，因此在pH检测方面具有良好的应用前景。
• Both visual and ratiometric fluorescent sensor for Zn2+ based on spirobenzopyran platform
  作者：Jian-Fa Zhu、Wing-Hong Chan、Albert W.M. Lee

  DOI：10.1016/j.tetlet.2012.02.031

  日期：2012.4

  A ratiometric fluorescent Zn2+ chemosensor, SPQH, based on spirobenzopyran platform, was synthesized. In aqueous HEPES 7.4 buffer solution, upon chelation with Zn(II), SPQH demonstrates high selectivity and subnanomolar sensitivity for zinc ion with 36-fold enhancement in the NIR fluorescence output. (C) 2012 Elsevier Ltd. All rights reserved.
• Reversible spiropyran-based chemosensor with pH-switches and application for bioimaging in living cells, Pseudomonas aeruginosa and zebrafish
  作者：Xiaojun He、Wei Xu、Chuchu Xu、Feng Ding、Hong Chen、Jianliang Shen

  DOI：10.1016/j.dyepig.2020.108497

  日期：2020.9

  Intracellular pH was tightly regulated in many biological processes in which cells must control pH changes within a precise range. Hence, tracing intracellular pH variation was important for understanding the physiological and pathological processes. Although fluorescent probes can be a necessary tool for detecting changes in pH, there are many limitations to existing probes, such as background interference, large cytotoxicity, and poor permeability, which need to be urgently overcome. In this work, a ratiometric and colorimetric chemosensor based on spiropyran (SP-DCCH) was fabricated for monitoring pH change using fluorescence resonance energy transfer mechanism. SP-DCCH has demonstrated the advantages of high sensitivity and selectivity, outstanding permeability and hypotoxicity. Moreover, SP-DCCH displays a pH-sensitive response from 1.68 to 7.21 (pKa = 4.87) and a linear response from pH 3.81 to 6.01, which was desirable for detecting pH change in living biosystem. As expected, the results confirmed that the response signal was pH-dependent and regulated via switchable forms between spiropyran and merocyanine. Spectacularly, SP-DCCH has successfully realized sensing and mapping pH in living cells, P. aeruginosa and zebrafish. The above results exhibited that SP-DCCH could be a powerful tool for sensing and visualizing pH in living systems.