3,8-diisopropyl-1,10-dihydro-benzo[e]pyrrolo[3,2-g]indole | 1246290-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,8-diisopropyl-1,10-dihydro-benzo[e]pyrrolo[3,2-g]indole
• 英文别名: 3,10-Di(propan-2-yl)-5,8-diazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),2(6),3,7(11),9,12,14-heptaene；3,10-di(propan-2-yl)-5,8-diazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),2(6),3,7(11),9,12,14-heptaene
• CAS: 1246290-48-1
• 化学式: C₂₀H₂₂N₂
• 分子量: 290.408
• InChiKey: ASGJRAGDSPKUKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,8-diisopropyl-1,10-dihydro-benzo[e]pyrrolo[3,2-g]indole 在 iron(III) chloride 、 硫酸 、 水 作用下， 以 二氯甲烷 为溶剂， 以13%的产率得到
  参考文献：
  名称：

  环[4]萘双吡咯：萘并双吡咯衍生的具有强近红外吸收性的环[8]吡咯

  摘要：

  扩展的卟啉：通过酸催化氧化偶联法从β-二烷基萘联吡咯中获得的环[4]萘联吡咯观察到了1273至1339 nm之间的强NIR吸收（见图）。相对于报道的烷基化环[8]吡咯，这些分子在其最低能带中表现出大的红移（161-228 nm），这是由于诱导的结构刚性和扩展的π共轭作用。

  DOI：

  10.1002/chem.201102486
• 作为产物：
  描述：

  4-甲基-2-氧代戊酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 、 乙二醇 为溶剂， 反应 30.0h， 生成 3,8-diisopropyl-1,10-dihydro-benzo[e]pyrrolo[3,2-g]indole
  参考文献：
  名称：

  Dinaphthoporphycenes: Synthesis and Nonlinear Optical Studies

  摘要：

  Naphthobipyrrole-derived porphycenes are synthesized for the first time via McMurry coupling of the beta-alkylated 2,9-diformylnaphthobipyrrole derivatives, which in turn were prepared easily from 2,3-naphthalene bishydrazine in four steps. Insertion of nickel into the porphycene core results in transformation of the rectangular N4-core into a square type geometry owing to the fusion of naphthalene moiety onto the bipyrrole entities. These porphycenes show large, intensity dependent three-photon absorption.

  DOI：

  10.1021/ol102378g

文献信息

• Dinaphthoporphycenes
  作者：Vladimir Roznyatovskiy、Vincent Lynch、Jonathan L. Sessler

  DOI：10.1021/ol101931y

  日期：2010.10.1

  Naphthobipyrrole is a potentially useful building block for porphyrin and porphyrin analogue synthesis. Reported here is a simple, generalizable synthetic route to α-formylated, β-substituted naphthobipyrroles and their use in the preparation of binaphthoporphycenes. The resulting binaphthoporphycenes possess a planar geometry as determined via a single-crystal X-ray diffraction analysis; they also

  Naphthobipyrrole 是卟啉和卟啉类似物合成的潜在有用构件。这里报道了一种简单、可推广的 α-甲酰化、β-取代萘并联吡咯的合成路线及其在制备双萘并卟啉中的用途。通过单晶 X 射线衍射分析确定，所得的双萘卟啉具有平面几何形状；与简单的卟啉相比，它们还显示出吸收最大值发生红移。
• Bis-naphthobipyrrolylmethene derived BODIPY complex: an intense near-infrared fluorescent dye
  作者：Tridib Sarma、Pradeepta K. Panda、Jun-ichiro Setsune

  DOI：10.1039/c3cc44834g

  日期：——

  Synthesis of a novel pi-extended BODIPY derived from naphthobipyrrole is presented. This dye molecule displays very intense near-infrared (NIR) absorption (epsilon > 400,000 M(-1) cm(-1)) and emission bands (>700 nm), accompanied by high quantum yield (phif = 0.65) owing to its extended pi-conjugation along with imposed structural rigidification.

  提出了一种新型的由萘双吡咯衍生的pi扩展的BODIPY的合成。该染料分子显示出非常强的近红外（NIR）吸收（ε> 400,000 M（-1）cm（-1））和发射带（> 700 nm），由于其高量子产率（phif = 0.65）扩展的pi共轭以及强加的结构刚性。
• Bis(naphthobipyrrolyl)methene-derived hexapyrrolic BODIPY as a single-molecule helicate with near-infrared emission
  作者：Sipra Sucharita Sahoo、Pradeepta K. Panda

  DOI：10.1039/d3cc02336b

  日期：——

  Helically twisted bis(naphthobipyrrolyl)methene-derived open-chain hexapyrroles have been synthesized as HCl salts and the corresponding BODIPY. Their solid-state structures elucidated by single-crystal X-ray diffraction analysis clearly showed the presence of intramolecular hydrogen bonds, which were concluded to play a pivotal role in stabilizing the twisted conformation. Both molecules were observed

  螺旋扭曲的双（萘并联吡咯基）亚甲基衍生的开链六吡咯已被合成为 HCl 盐和相应的 BODIPY。通过单晶X射线衍射分析阐明的它们的固态结构清楚地表明分子内氢键的存在，这被认为在稳定扭曲构象方面发挥着关键作用。观察到这两种分子均具有近红外活性，其中 BODIPY 部分发射范围超过 800 nm。
• π-Extension in Expanded Porphyrins: Cyclo[4]naphthobipyrrole
  作者：Vladimir V. Roznyatovskiy、Jong Min Lim、Vincent M. Lynch、Byung Sun Lee、Dongho Kim、Jonathan L. Sessler

  DOI：10.1021/ol2023449

  日期：2011.10.21

  The pi-extended cyclo[4]naphthoblpyrrole la has been prepared via an Fe(III)-mediated oxidative cyclization of an alkyl-substituted naphthoblpyrrole. The structure of this new expanded porphyrin, isolated as the deprotonated sulfate salt, was characterized by spectroscopic means, as well through a single crystal X-ray diffraction analysis. Salt la displays a total of four well-resolved redox waves as determined by cyclic voltammetry. It also displays bathochromically shifted near-IR absorption maxima compared to the diprotonated forms of nonannulated cyclo[8]pyrroles.
• Dinaphthoporphycenes: Synthesis and Nonlinear Optical Studies
  作者：Tridib Sarma、Pradeepta K. Panda、P. T. Anusha、S. Venugopal Rao

  DOI：10.1021/ol102378g

  日期：2011.1.21

  Naphthobipyrrole-derived porphycenes are synthesized for the first time via McMurry coupling of the beta-alkylated 2,9-diformylnaphthobipyrrole derivatives, which in turn were prepared easily from 2,3-naphthalene bishydrazine in four steps. Insertion of nickel into the porphycene core results in transformation of the rectangular N4-core into a square type geometry owing to the fusion of naphthalene moiety onto the bipyrrole entities. These porphycenes show large, intensity dependent three-photon absorption.