diethyl 3,3'-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-ylmethylene)bis(4,5,6,7-tetrahydro-2Hisoindole-1-carboxylate) | 1379997-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: diethyl 3,3'-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-ylmethylene)bis(4,5,6,7-tetrahydro-2Hisoindole-1-carboxylate)
• 英文别名: ethyl 3-[(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindol-1-yl)-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)methyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
• CAS: 1379997-00-8
• 化学式: C₃₇H₄₈N₂O₉
• 分子量: 664.796
• InChiKey: JKJJHYCFIGLAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl 3,3'-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-ylmethylene)bis(4,5,6,7-tetrahydro-2Hisoindole-1-carboxylate) 在 三氟化硼乙醚 、 silica gel 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 甲苯 为溶剂， 生成 ethyl 3-[(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)carbonyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  Diethyl (biscyclohexano)BODIPY dicarboxylates. Chelation of alkaline-earth metal ions and sensor properties

  摘要：

  meso-Aryl-substituted (biscyclohexano)bis(ethoxycarbonyl)BODIPY [aryl = phenyl, 3,4-dimethoxyphenyl, and 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl-(m-{benzo-15-crown-5}-yl)] were synthesized. The effect of alkaline-earth metals on the absorption and fluorescence spectra of these compounds was investigated. In all compounds along with the mechanism of the photoinduced electron transfer (PET), well-known for the crown-containing BODIPY-based sensors, one more response pattern is observed. The large excess of Ca2+ and Ba2+ ions in the system leads to the changes both in the UV-Vis and emission spectra. The complex formation results in the decrease of emission intensity and in its red shift. Besides, a new longwave absorption band appears in the UV-Vis spectrum of the BODIPY-metal ion complex. The formation constants of the complexes corresponding to this response pattern is about 100 times less than the formation constant of Ca2+-crown ether complex. H-1, C-13, B-11, and F-19 NMR spectra, the results of quantum-chemical calculations, and their comparison with the literature data of X-ray diffraction study suggest that the binding of Ca2+ and Ba2+ ions occurs in the cavity formed by the fluorine atoms and the carbonyl oxygen atoms of the ester groups.

  DOI：

  10.1134/s1070428014020158
• 作为产物：
  描述：

  4-甲酰-15-冠-5 、 4,5,6,7-四氢异吲哚-1-羧酸乙酯 在 三氟化硼乙醚 、 四丁基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以69%的产率得到diethyl 3,3'-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-ylmethylene)bis(4,5,6,7-tetrahydro-2Hisoindole-1-carboxylate)
  参考文献：
  名称：

  双环己烷环化二吡啶二甲酸二乙酯：观察没有可见吸收的双吡喃形式

  摘要：

  已经合成了一系列 2,3;7,8-双环己基稠合二乙基 5-芳基二吡喃-1,9-二羧酸酯 [芳基 = 苯基, 3,4-二甲氧基苯基和 2,3,5,6,8,9, 11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine-15-yl (m-benzo-15-crown-5)]。所得化合物在溶液中以两种平衡形式存在，一种具有可见吸收带（λabs 468-485 nm），另一种是“可见-无声”形式，在可见光区没有吸收带。“可见-沉默”形式已被分离出来并通过核磁共振分析表征，包括二维技术。还进行了量子化学计算，产生了两个主要构象，氮原子的近距和远距排列。在后一种构象中，发现吡咯-吡咯片段几乎是正交的，没有长的共轭链。计算结果证实了光谱结果。两种不同的形式也被表征为它们的 Mg2+ 络合物，并通过 UV/Vis 和 NMR 光谱分析进行研究，并注意到明显的差异。

  DOI：

  10.1002/ejoc.201101729

文献信息

• Biscyclohexane-Annulated Diethyl Dipyrrindicarboxylates: Observation of a Dipyrrin Form with Absent Visible Absorption
  作者：Ksenia Tikhomirova、Alexander Anisimov、Andrey Khoroshutin

  DOI：10.1002/ejoc.201101729

  日期：2012.4

  8-biscyclohexano-fused diethyl 5-aryldipyrrin-1,9-dicarboxylates have been synthesized [aryl = phenyl, 3,4-dimethoxyphenyl and 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine-15-yl (m-benzo-15-crown-5)]. The obtained compounds were shown to exist in two equilibrium forms in solution, with one exhibiting a visible absorption band (λabs 468–485 nm), and the other, “vis-silent” form, having no

  已经合成了一系列 2,3;7,8-双环己基稠合二乙基 5-芳基二吡喃-1,9-二羧酸酯 [芳基 = 苯基, 3,4-二甲氧基苯基和 2,3,5,6,8,9, 11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine-15-yl (m-benzo-15-crown-5)]。所得化合物在溶液中以两种平衡形式存在，一种具有可见吸收带（λabs 468-485 nm），另一种是“可见-无声”形式，在可见光区没有吸收带。“可见-沉默”形式已被分离出来并通过核磁共振分析表征，包括二维技术。还进行了量子化学计算，产生了两个主要构象，氮原子的近距和远距排列。在后一种构象中，发现吡咯-吡咯片段几乎是正交的，没有长的共轭链。计算结果证实了光谱结果。两种不同的形式也被表征为它们的 Mg2+ 络合物，并通过 UV/Vis 和 NMR 光谱分析进行研究，并注意到明显的差异。
• Diethyl (biscyclohexano)BODIPY dicarboxylates. Chelation of alkaline-earth metal ions and sensor properties
  作者：K. V. Tikhomirova、A. V. Khoroshutin、A. V. Anisimov

  DOI：10.1134/s1070428014020158

  日期：2014.2

  meso-Aryl-substituted (biscyclohexano)bis(ethoxycarbonyl)BODIPY [aryl = phenyl, 3,4-dimethoxyphenyl, and 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl-(m-benzo-15-crown-5}-yl)] were synthesized. The effect of alkaline-earth metals on the absorption and fluorescence spectra of these compounds was investigated. In all compounds along with the mechanism of the photoinduced electron transfer (PET), well-known for the crown-containing BODIPY-based sensors, one more response pattern is observed. The large excess of Ca2+ and Ba2+ ions in the system leads to the changes both in the UV-Vis and emission spectra. The complex formation results in the decrease of emission intensity and in its red shift. Besides, a new longwave absorption band appears in the UV-Vis spectrum of the BODIPY-metal ion complex. The formation constants of the complexes corresponding to this response pattern is about 100 times less than the formation constant of Ca2+-crown ether complex. H-1, C-13, B-11, and F-19 NMR spectra, the results of quantum-chemical calculations, and their comparison with the literature data of X-ray diffraction study suggest that the binding of Ca2+ and Ba2+ ions occurs in the cavity formed by the fluorine atoms and the carbonyl oxygen atoms of the ester groups.