2-ethoxycarbonyl-4,7-dihydro-2H-isoindole | 1029092-45-2

• 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: 2-ethoxycarbonyl-4,7-dihydro-2H-isoindole
• 英文别名: ethyl 4,7-dihydroisoindole-1-carboxylate；ethyl 4,7-dihydro-2H-isoindole-1-carboxylate；α-ethoxycarbonyl-4,7-dihydroisoindole；4,7-Dihydro-2H-isoindole-1-carboxylic acid ethyl ester
• CAS: 1029092-45-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: NPMGKZYSVKFVSF-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  370.7±42.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethoxycarbonyl-4,7-dihydro-2H-isoindole 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 0.5h， 以65%的产率得到4,7-dihydro-2H-isoindole
  参考文献：
  名称：

  自组装四苯并四苯基卟啉锌和Per二酰亚胺带电管道中的光驱动电荷分离和传输

  摘要：

  共价连接到四个per二酰亚胺（PDI）受体上的四苯并四苯基卟啉锌（ZnTBTPP）自组装成π堆叠，分离的柱状结构，如小角度和广角X射线散射所示。ZnTBTPP的光激发迅速产生了寿命长的电子-空穴对，其平均分离距离为26Å，比该对电子-空穴对被限制在共价单体中的距离长得多。这意味着电荷在它们各自隔离的ZnTBTPP和PDI电荷管道中可以移动。

  DOI：

  10.1002/anie.201309335
• 作为产物：
  描述：

  邻氯苯硫酚 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-ethoxycarbonyl-4,7-dihydro-2H-isoindole
  参考文献：
  名称：

  自组装四苯并四苯基卟啉锌和Per二酰亚胺带电管道中的光驱动电荷分离和传输

  摘要：

  共价连接到四个per二酰亚胺（PDI）受体上的四苯并四苯基卟啉锌（ZnTBTPP）自组装成π堆叠，分离的柱状结构，如小角度和广角X射线散射所示。ZnTBTPP的光激发迅速产生了寿命长的电子-空穴对，其平均分离距离为26Å，比该对电子-空穴对被限制在共价单体中的距离长得多。这意味着电荷在它们各自隔离的ZnTBTPP和PDI电荷管道中可以移动。

  DOI：

  10.1002/anie.201309335

文献信息

• Pd and Pt Complexes of Benzo-Fused Dipyrrins: Synthesis, Structure, Electrochemical, and Optical Properties
  作者：Graden Snyder、Sara Abuhadba、Neo Lin、Wei-Tsung Lee、Tomoyasu Mani、Tatiana V. Esipova

  DOI：10.1021/acs.inorgchem.4c00055

  日期：2024.7.1

  Benzo-fused dipyrrins are π-extended analogs of conventional dipyrrins, which exhibit bathochromically shifted absorption and possess the synthetic capability to bind various metal ions. We aimed to investigate the synthetic potential of benzo-fused dipyrrins in the complexation with transition metals. Two new complexes with Pd2+ and Pt2+ were synthesized and characterized. X-ray crystallography reveals

  苯并稠合二吡林是传统二吡林的π-延伸类似物，其表现出红移吸收并具有结合各种金属离子的合成能力。我们的目的是研究苯并稠合二吡啉在与过渡金属络合中的合成潜力。合成并表征了两种新的Pd 2+和Pt 2+配合物。 X 射线晶体学表明，两种配合物均呈现锯齿形几何形状，中心金属具有方形平面配位。 Pd 2+络合物在665 nm处具有非常弱的荧光，而Pt 2+络合物完全不发射。瞬态吸收光谱证实了两种配合物的三重激发态形成；然而，它们的寿命很短，即使在 77K 下也没有观察到磷光。 DFT 计算支持了实验观察，揭示了低位配体-金属电荷转移（LMCT）三重态作为能量汇的存在。
• 4,8-Dihydropyrrol[3,4-f]isoindole as a Useful Building Block for Near-Infrared Dyes
  作者：Hidemitsu Uno、Mitsunori Nakamura、Kazuki Jodai、Shigeki Mori、Tetsuo Okujima

  DOI：10.3987/com-14-s(k)91

  日期：——

  4,8-Dihydropyrrol[3,4-f]isoindole was prepared from 4,7-dihydroisoindole based on the modified Barton-Zard reaction. Addition of phenylsulfenyl chloride followed by oxidation and dehydrochlorination gave phenylsulfonyldihydroisoindole, which underwent the smooth reaction with an isocyanoacetate under basic conditions to give 4,8-dihydropyrrol[3,4-f]isoindole-1,5- and 1,7-dicarboxylates in good yields. The pyrrolisoindole was successfully converted to the benzene-fused bisBODIPY, absorption maximum of which was 758 nm.
• JP2015/40176
  申请人：——

  公开号：——

  公开（公告）日：——
• JP6086526
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of 5,15-Diaryltetrabenzoporphyrins
  作者：Mikhail A. Filatov、Artem Y. Lebedev、Sergei A. Vinogradov、Andrei V. Cheprakov

  DOI：10.1021/jo800509k

  日期：2008.6.1

  A general method of synthesis of 5,15-diaryltetrabenzoporphyrins (Ar(2)TBPs) has been developed, based on 2 + 2 condensation of dipyrromethanes followed by oxidative aromatization. Two pathways to Ar(2)TBPs were investigated: the tetrahydroisoindole pathway and the dihydroisoindole pathway. In the tetrahydroisoindole pathway, precursor 5,15-diaryltetracyclohexenoporphyrins (5,15-Ar(2)TCHPs) were assembled from cyclohexeno-fused meso-unsubstituted dipyrromethanes and aromatic aldehydes or, alternatively, by way of the classical MacDonald synthesis. In the first case, scrambling was observed. Aromatization by tetracyclone was more effective than aromatization by DDQ but failed in the cases of porphyrins with electron-withdrawing substituents in the meso-aryl rings. The dihydroisoindole pathway was found to be much superior to the tetrahydroisoindole pathway, and it was developed into a general preparative method, consisting of (1) the synthesis of 4,7-dihydroisoindole and its transformation into meso-unsubstituted dipyrromethanes, (2) the synthesis of 5,15-diaryloctahydrotetrabenzoporphyrins (5,15-Ar(2)OHTBPs), and (3) their subsequent aromatization by DDQ. Ar2TBP free bases exhibit optical absorption spectra similar to those of meso-unsubstituted tetrabenzoporphyrins and fluoresce with high quantum yields. Pd complex of Ph2TBP was found to be highly phosphorescent at room temperature.