2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one | 554433-41-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 异卟啉
• 英文名称: 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one
• 英文别名: 16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17)-heptaen-8-one
• CAS: 554433-41-9
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: SWXXZNFUWOJCOC-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  416.4±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one 在 palladium on activated charcoal 作用下， 以 苯 为溶剂， 反应 2.0h， 以81%的产率得到7H-二苯并[de,H]喹啉-7-酮
  参考文献：
  名称：

  新氧代异皂啡的 1 H 和 13 C NMR 谱的合成和全归属的长程异核相关

  摘要：

  新型氧代异皂啡类 7H-二苯并[de,h]quinolin-7-one, 5-甲氧基-7H-二苯并[de,h]quinolin-7-one, 5-甲氧基-6-羟基-7H-二苯并[de,h] ]喹啉-7-酮、5-羟基-7H-二苯并[de,h]喹啉-7-one和5-甲氧基-6H-二苯并[de,h]喹啉-6-酮是通过将它们的 2 ,3-二氢衍生物或通过在 100 °C 下加热（2'-（3,4-二氢-6,7-二甲氧基异喹啉-1'-基）苯基）甲基苯甲酸酯与乙酸/硫酸混合物。结构得到确认，1H 和 13C NMR 光谱使用二维 NMR 技术完全确定。版权所有 © 2005 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.1703
• 作为产物：
  描述：

  2,3-dihydro-3-hydroxy-2-(2-phenylethyl)-1H-isoindol-1-one 在 盐酸 、 硫酸 、 三氧化硫 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 56.0h， 生成 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of some 1-azabenzanthrone derivatives

  摘要：

  Some synthetic 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones) are weakly to moderately cytotoxic, suggesting that they might also show antiparasitic activity. We have now tested a small collection of these compounds in vitro against a chloroquine-resistant Plasmodium falciparum strain, comparing their cytotoxicity against normal human fibroblasts. Our results indicate that 5-methoxy-1-azabenzanthrone and its 2,3-dihydro analogue have low micromolar antiplasmodial activities and showed more than 10-fold selectivity against the parasite, indicating that the dihydro compound, in particular, might serve as a lead compound for further development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.092
• 作为试剂：
  描述：

  三乙胺 在 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one 作用下， 以 氘代乙腈 为溶剂， 生成 1-(N,N-二乙氨基)-1,3-丁二烯 、 乙醛 、 二乙胺
  参考文献：
  名称：

  Unexpected Formation of 1-Diethylaminobutadiene in Photosensitized Oxidation of Triethylamine Induced by 2,3-Dihydro-oxoisoaporphine Dyes. A ¹H NMR and Isotopic Exchange Study

  摘要：

  [GRAPHIC]Photoreduction of oxoisoaporphine dyes occurs via a stepwise mechanism of electron-protonelectron transfer that leads to the N-hydrogen oxoisoaporphine anion. When triethylamine, TEA, was used as the electron donor in anaerobic conditions, 1-diethylaminobutadiene, DEAB, was one of the oxidation products of TEA, among diethylamine and acetaldehyde. DEAB was identified by H-1 NMR and GC-MS experiments by comparison with the authentic 1-diethylaminobutadiene. This is the first report of a butadienyl derivative formed in the dye-sensitized photooxidation of TEA. In addition, isotopic exchange experiments with TEA-d(15) and D2O show that the hydrogens at carbon-2 and carbon-4 of the butadienyl moiety are exchangeable. The observed isotopic exchange pattern could be explained by the head-to-tail coupling of an N,N-diethylvinylamine intermediate that exchanges hydrogens at the C-beta via the enammonium ion.

  DOI：

  10.1021/jo050796q

文献信息

• Complete structural and spectral assignment of oxoisoaporphines by HMQC and HMBC experiments
  作者：Eduardo Sobarzo-Sánchez、Bruce K. Cassels、Carolina Jullian、Luis Castedo

  DOI：10.1002/mrc.1177

  日期：2003.4

  The oxoisoaporphines 2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one, 2,3‐dihydro‐5‐methoxy‐7H‐dibenzo [de,h] quinolin‐7‐one, 5‐methoxy‐6‐hydroxy‐2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one, 5,6‐dimethoxy‐2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one and 5,6‐methylenedi‐oxy‐2,3‐dihydro‐7H‐dibenzo[de,h]quinolin‐7‐one were prepared by cyclization of phenylethylaminophthalides with polyphosphoric acid or by treating

  2,3-二氢-7H-二苯并[de,h]喹啉-7-酮、2,3-二氢-5-甲氧基-7H-二苯并[de,h]喹啉-7-酮、5-甲氧基-7-酮6-羟基-2,3-二氢-7H-二苯并[de,h]喹啉-7-one, 5,6-二甲氧基-2,3-二氢-7H-二苯并[de,h]喹啉-7-one和5,6-methylenedi-oxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one 通过苯乙氨基苯酞与多磷酸的环化或通过处理 1-(2-carboxyphenyl)-3,4 制备-二氢异喹啉盐酸盐与硫酸在 0 °C 下反应。使用一维和二维核磁共振技术的组合确认了结构，并完全确定了 1H 和 13C 核磁共振谱。版权所有 © 2003 John Wiley & Sons, Ltd.
• Annulation of substituted anthracene-9,10-diones yields promising selectively antiproliferative compounds
  作者：Vicente Castro-Castillo、Cristian Suárez-Rozas、Natalia Castro-Loiza、Cristina Theoduloz、Bruce K. Cassels

  DOI：10.1016/j.ejmech.2013.01.049

  日期：2013.4

  Anthraquinone derivatives are well-known antiproliferative compounds, and some are currently used in cancer chemotherapy. Some families of annulated anthraquinone analogs have also been examined for antiproliferative activity, but in this regard almost nothing is known of 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones). A series of 1-azabenzanthrone derivatives, their 2,3-dihydro analogs, and

  蒽醌衍生物是众所周知的抗增殖化合物，目前一些被用于癌症化学疗法中。还已经研究了一些环状的蒽醌​​类似物的抗增殖活性，但是在这方面，几乎没人知道1-氮杂苯并蒽酮（7 H-二苯并[ de，h ]喹啉-7-酮）。测试了一系列的1-氮杂苯并蒽醌衍生物，它们的2,3-二氢类似物和同等取代的9,10-蒽二酮对正常的人类成纤维细胞和四种人类癌细胞系。多数杂环化合物被证明对IC 50具有弱至中度的抗增殖作用该值向下延伸至0.86μM，并且在癌症和正常细胞之间表现出高达30倍的选择性。1-氮杂苯并蒽酮和1-氮杂-2,3-二氢苯并蒽酮均比蒽醌类更有效，几乎毫无例外，2,3-二氢化合物比完全芳族的1-氮杂苯并蒽酮更有效。
• Complete¹H and¹³C NMR spectral assignment of hydrogenated oxoisoaporphine derivatives
  作者：Eduardo Sobarzo-Sánchez、Bruce K. Cassels、Luis Castedo

  DOI：10.1002/mrc.1205

  日期：2003.7

  [de,h]quinolin‐7‐ol were prepared by catalytic hydrogenation of oxoisoaporphines or their 2,3‐dihydro derivatives over PtO2 in acetic acid under mild conditions. Their structures were confirmed and 1H and 13C NMR spectra were completely assigned using a combination of one‐ and two‐dimensional NMR techniques. Copyright © 2003 John Wiley & Sons, Ltd.

  2,3,8,9,10,11-Hexahydro-7H-dibenzo[de,h]quinolin-7-one, 5-甲氧基-2,3,8,9,10,11-hexahydro-7H-dibenzo[ de,h]quinolin-7-one, 5-methoxy-6-hydroxy-1,2,3,7a,8,9,10,11,11a,11b-decahydro-7H-dibenzo[de,h]quinolin- 7-one, 5-甲氧基-5,6,8,9,10,11-六氢-4H-二苯并[de,h]quinolin-7-ol, 5,6,8,9,10,11-六氢- 4H-二苯并[de,h]喹啉-7-醇和5,6-二氢-4H-二苯并[de,h]喹啉-7-醇是通过氧代异皂甙或其2,3-二氢衍生物在PtO2上催化加氢制备的在温和条件下在乙酸中。使用一维和二维核磁共振技术的组合确认了它们的结构，并完全确定了 1H 和
• Synthesis and total assignment of1H and13C NMR spectra of new oxoisoaporphines by long-range heteronuclear correlations
  作者：Eduardo Sobarzo-Sánchez、Julio De la Fuente、Luis Castedo

  DOI：10.1002/mrc.1703

  日期：2005.12

  new oxoisoaporphines 7H‐dibenzo[de,h]quinolin‐7‐one, 5‐methoxy‐7H‐dibenzo[de,h]quinolin‐7‐one, 5‐methoxy‐6‐hydroxy‐7H‐dibenzo[de,h]quinolin‐7‐one, 5‐hydroxy‐7H‐dibenzo[de,h]quinolin‐7‐one and 5‐methoxy‐6H‐dibenzo[de,h]quinolin‐6‐one were prepared either by oxidation of their 2,3‐dihydro derivatives or by heating (2′‐(3,4‐dihydro‐6,7‐dimethoxyisoquinolin‐1′‐yl)phenyl)methylbenzoate with an acetic acid/sulfuric

  新型氧代异皂啡类 7H-二苯并[de,h]quinolin-7-one, 5-甲氧基-7H-二苯并[de,h]quinolin-7-one, 5-甲氧基-6-羟基-7H-二苯并[de,h] ]喹啉-7-酮、5-羟基-7H-二苯并[de,h]喹啉-7-one和5-甲氧基-6H-二苯并[de,h]喹啉-6-酮是通过将它们的 2 ,3-二氢衍生物或通过在 100 °C 下加热（2'-（3,4-二氢-6,7-二甲氧基异喹啉-1'-基）苯基）甲基苯甲酸酯与乙酸/硫酸混合物。结构得到确认，1H 和 13C NMR 光谱使用二维 NMR 技术完全确定。版权所有 © 2005 John Wiley & Sons, Ltd.
• An Expedient Synthesis of Unusual Oxoisoaporphine and Annelated Quinoline Derivatives
  作者：Eduardo Sobarzo-Sánchez、Bruce K. Cassels、Luis Castedo

  DOI：10.1055/s-2003-41422

  日期：——

  isoaporphine and quinoline derivatives, due to its simp- licity and efficiency. The dihydro- and oxoisoaporphines used in this work and the generated products are summarized in Table 1. In all cases, hydrogenation was carried out for 24 hours at room temperature at pressures between 60-70 psi. 8 Under these conditions, complete or partial reduction of aromatic ring D and of the C-N imine bond of the dihydrooxoisoapor-

  几种 2,3-二氢-7H-二苯并(de,h)quinolin-7-ones 和 7H-dibenzo(de,h)quinolin-7-ones 在 PtO2 上在乙酸中催化氢化得到 7-羟基喹啉和具有还原苯环的喹诺酮衍生物。有限数量的具有 7H-二苯并 (de,h) 喹啉骨架的化合物，称为 1-氮杂苯，在三十年前作为染料形成的中间体被合成，1 并且由于它们可能的光和电化学性质。2 大约在同一时间，通过 N-苯乙基邻苯二甲酰亚胺合成 7H-二苯并(de,h) 喹啉-7-one 衍生物的报道与它们可能的抗病毒活性有关，3 和一些 2,3-二氢还报道了通过环化 3-(b-二烷氧基芳基乙基氨基)邻苯二甲醚的衍生物。4 对于 5-甲氧基-2,3-二氢类似物 (2)，这种化合物的数量足够大，可以对其进行一些初步的还原研究，得到一种碱性甲醇，但其结构尚未得到充分证实。自 1980 年代以来，已从 Menispermum

表征谱图