2-(2,2-dimethoxyethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione | 153721-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2,2-dimethoxyethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione
• 英文别名: 2-(2,2-dimethoxyethyl)benzo[de]isoquinoline-1,3-dione；N-[2,2-(dimethoxy)ethane]-1,8-naphthalimide
• CAS: 153721-06-3
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: IPQNHLBUWYQHDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,2-dimethoxyethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-(2-((2-(3′,6′-bis(diethylamino)-3-oxospiro[isoindoline-1,9′-xanthen]-2-yl)ethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  A 1,8 naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ion in living cells

  摘要：

  A 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehydeanchored rhodamine B based probe, RDNAP detects Cr3+ ion by fluorescence resonance energy transfer (FRET) process in aqueous buffered acetonitrile media (7:3, v/v). Conversely, conjugation of 2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl) acetaldehyde with rhodamine B provides another probe, RDNAP-PY that undergoes Cr3+ assisted ratiometric fluorescence and colorimetric change in the same media. RDNAP-PY provides higher FRET efficiency and detects as low as 1.81 x 10(-6) M Cr3+ with an association constant, 15.9 x 104 M-1. Other common ions do not interfere. RDNAP-PY efficiently images intracellular Cr3+ in live Hep3B, MCF-7, HeLa, SiHa and HEK 293T cells under fluorescence microscope in a ratiometric and time dependent manner. H-1 NMR titration and DFT studies strongly support experimental findings.

  DOI：

  10.1016/j.jphotochem.2018.12.010
• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 氨基乙醛缩二甲醇 以 乙醇 为溶剂， 以97%的产率得到2-(2,2-dimethoxyethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  作为PhotoCORM的 新型模块化锰（i）三羰基锰配合物：使用COP-1作为荧光开关探针在体外检测光诱导的一氧化碳释放†

  摘要：

  基于三齿双（吡唑基）乙胺（bpea）的五种通式为[Mn（bpea N CHC6H4R）（CO）3 ] PF 6和[Mn（bpea NHCH2C6H4R）（CO）3 ] PF 6的锰（I）三羰基配合物）合成并充分表征了每个配体，每个配体均包含一个带有4个取代基的侧基，R = H，I和C C–H，包括X射线结构分析的三种化合物。所有复合物在黑暗中在水性缓冲液中稳定较长时间。但是，CO释放可以通过在365 nm处照射来触发，从而将这些化合物确立为新型的可光活化的CO释放分子（PhotoCORM）。亚胺的影响与。借助DFT和TDDFT计算研究了电子结构和光物理行为的配体中的胺基。通过对所选化合物进行溶液IR研究，可以鉴定出由光反应产生的中间体。最后，使用COP-1作为荧光开关探针，在PBS缓冲液中和体外在人脐静脉内皮细胞（HUVEC）中都证明了光诱导的CO从模型化合物释放。

  DOI：

  10.1039/c4dt00254g

文献信息

• Directional control of π-stacked building blocks for crystal engineering: the 1,8-naphthalimide synthon
  作者：Daniel L. Reger、J. Derek Elgin、Radu F. Semeniuc、Perry J. Pellechia、Mark D. Smith

  DOI：10.1039/b504998a

  日期：——

  Incorporating the 1,8-naphthalimide group into bis(pyrazolyl)methane ligands triggers the association of their rhenium(I) complexes into directionally ordered dimers in both solution and solid state, as demonstrated by ES+/MS, PGSE–NMR and X-ray diffraction studies.

  正如 ES+/MS、PGSEâNMR 和 X 射线衍射研究证明的那样，在双（吡唑基）甲烷配体中加入 1,8-萘二甲酰亚胺基团，可促使其铼（I）配合物在溶液和固体状态下形成定向有序的二聚体。
• First row transition metal complexes of a hexadentate pyrazole-based bispidine ligand
  作者：Peter Comba、Michael Morgen、Hubert Wadepohl

  DOI：10.1016/j.poly.2012.06.035

  日期：2013.3

  The efficient synthesis of a new hexadentate pyrazole-based bispidine-ligand and its first-row transition metal complexes (Fe-II, Co-II, Ni-II, Cu-II and zn(II)) is reported. There are interesting structural differences between the present and earlier hexadentate bispidine ligands (tetragonally versus trigonally distorted octahedral geometries). The structural analysis of the metal-free ligand and the five complexes shows that the structure enforced by the rigid pyrazole-based bispidine is best described as distorted trigonal prismatic, and this also emerges from the spectroscopic analysis. (C) 2012 Elsevier Ltd. All rights reserved.
• Saito; Takayama; Sakurai, Journal of the American Chemical Society, 1994, vol. 116, # 6, p. 2653 - 2654
  作者：Saito、Takayama、Sakurai

  DOI：——

  日期：——
• A 1,8 naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ion in living cells
  作者：Susanta Adhikari、Sabyasachi Ta、Avijit Ghosh、Subhajit Guria、Abhishek Pal、Manisha Ahir、Arghya Adhikary、Sumit Kumar Hira、Partha Pratim Manna、Debasis Das

  DOI：10.1016/j.jphotochem.2018.12.010

  日期：2019.3

  A 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehydeanchored rhodamine B based probe, RDNAP detects Cr3+ ion by fluorescence resonance energy transfer (FRET) process in aqueous buffered acetonitrile media (7:3, v/v). Conversely, conjugation of 2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl) acetaldehyde with rhodamine B provides another probe, RDNAP-PY that undergoes Cr3+ assisted ratiometric fluorescence and colorimetric change in the same media. RDNAP-PY provides higher FRET efficiency and detects as low as 1.81 x 10(-6) M Cr3+ with an association constant, 15.9 x 104 M-1. Other common ions do not interfere. RDNAP-PY efficiently images intracellular Cr3+ in live Hep3B, MCF-7, HeLa, SiHa and HEK 293T cells under fluorescence microscope in a ratiometric and time dependent manner. H-1 NMR titration and DFT studies strongly support experimental findings.
• New modular manganese(i) tricarbonyl complexes as PhotoCORMs: in vitro detection of photoinduced carbon monoxide release using COP-1 as a fluorogenic switch-on probe
  作者：Sandesh Pai、Maryam Hafftlang、George Atongo、Christoph Nagel、Johanna Niesel、Svetlana Botov、Hans-Günther Schmalz、Benito Yard、Ulrich Schatzschneider

  DOI：10.1039/c4dt00254g

  日期：——

  as novel photoactivatable CO-releasing molecules (PhotoCORMs). The influence of the imine vs. amine group in the ligands on the electronic structure and the photophysical behavior was investigated with the aid of DFT and TDDFT calculations. Solution IR studies on selected compounds allowed identification of intermediates resulting from the photoreaction. Finally, light-induced CO release from a model

  基于三齿双（吡唑基）乙胺（bpea）的五种通式为[Mn（bpea N CHC6H4R）（CO）3 ] PF 6和[Mn（bpea NHCH2C6H4R）（CO）3 ] PF 6的锰（I）三羰基配合物）合成并充分表征了每个配体，每个配体均包含一个带有4个取代基的侧基，R = H，I和C C–H，包括X射线结构分析的三种化合物。所有复合物在黑暗中在水性缓冲液中稳定较长时间。但是，CO释放可以通过在365 nm处照射来触发，从而将这些化合物确立为新型的可光活化的CO释放分子（PhotoCORM）。亚胺的影响与。借助DFT和TDDFT计算研究了电子结构和光物理行为的配体中的胺基。通过对所选化合物进行溶液IR研究，可以鉴定出由光反应产生的中间体。最后，使用COP-1作为荧光开关探针，在PBS缓冲液中和体外在人脐静脉内皮细胞（HUVEC）中都证明了光诱导的CO从模型化合物释放。