benzo[b]pyrido[4,3,2-de]quinolino[2,3,4-gh][1,10]phenanthroline | 161068-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: benzo[b]pyrido[4,3,2-de]quinolino[2,3,4-gh][1,10]phenanthroline
• 英文别名: isoeilatin；3,13,16,26-Tetrazaheptacyclo[13.11.1.12,10.04,9.017,22.023,27.014,28]octacosa-1(26),2,4,6,8,10(28),11,13,15,17,19,21,23(27),24-tetradecaene；3,13,16,26-tetrazaheptacyclo[13.11.1.12,10.04,9.017,22.023,27.014,28]octacosa-1(26),2,4,6,8,10(28),11,13,15,17,19,21,23(27),24-tetradecaene
• CAS: 161068-60-6
• 化学式: C₂₄H₁₂N₄
• 分子量: 356.386
• InChiKey: XDEVBVOSOVLMDK-UHFFFAOYSA-N

物化性质

• 沸点：
  675.4±25.0 °C(Predicted)
• 密度：
  1.502±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 Λ-[Ru(bpy)2(py)2][(-)-O,O'-dibenzoyl-L-tartrate]*12H2O 、 benzo[b]pyrido[4,3,2-de]quinolino[2,3,4-gh][1,10]phenanthroline 以 乙二醇 为溶剂， 以45%的产率得到Δ-[Ru(2,2'-bipyridine)2(isoeilatin)][PF6]2*2.5H2O
  参考文献：
  名称：

  π-Stacking Induced NMR Spectrum Splitting in Enantiomerically Enriched Ru(II) Complexes:  Evaluation of Enantiomeric Excess

  摘要：

  Several chiral octahedral complexes of the general formula [Ru(bpy)(2)(Lig)][PF6](2) (Lig = a ligand that can participate in pi-stacking interactions such as eilatin, isoeilatin, and tpphz) were synthesized in both the racemic and enantiomerically pure/enriched forms. Nonracemic mixtures of enantiomers of all these complexes exhibit splitting of the H-1 NMR spectra (NMR nonequivalence); i.e., each spectrum contains a major and a minor set of peaks. The origin of this phenomenon is attributed to a fast equilibrium between monomers and discrete dimers held together by pi-stacking interactions, and it is observed for a wide range of pi-stacking interaction strengths. The NMR spectrum splitting exhibited by these complexes can be exploited for the evaluation of their enantiomeric excess simply from the integral ratio, without addition of chiral shift reagents.

  DOI：

  10.1021/ic048569e
• 作为产物：
  描述：

  9-methyl-3,4-dihydroacridin-1(2H)-one 在 manganese(IV) oxide 、 cerium(III) chloride heptahydrate 、 硫酸 、 氯化铵 、 溶剂黄146 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.33h， 生成 benzo[b]pyrido[4,3,2-de]quinolino[2,3,4-gh][1,10]phenanthroline
  参考文献：
  名称：

  海洋吡啶并ac啶生物碱全素及其合成异构体异全素的全合成方法不同

  摘要：

  在本文中，我们报道了七环吡啶并r啶生物碱角蛋白（1）及其合成异构体异角蛋白（2）的总合成。从容易获得的9-甲基-3,4-二氢ac啶-1-1（2 H）-一（5）和2-氨基苯乙酮开始，发散合成得到七分之一的生物碱1和八分之一的异构体2。

  DOI：

  10.1016/j.tetlet.2015.01.176

文献信息

• The biomimetic synthesis of marine alkaloid related pyrido- and pyrrolo[2,3,4-kl]acridines
  作者：Gari Gellerman、Amira Rudi、Yoel Kashman

  DOI：10.1016/s0040-4020(01)81215-1

  日期：1994.1

  reaction between β,β′-diamenoketones (e.g. kynuramine, kynurenine or o,o′-diaminobenzophenone) and a variety cyclohexanediones and quinones leading to pyrido[2,3,4-kl) acridines is described. The synthesis of several di- and tetrahydro-pyrido[2,3,4-kl)acridine derivatives (7, 10. 12 and 15) as well as benzoderivatives of the marine alkaloids eilatin (1) and ascididemin (2), compounds 28 and 30, has

  β，β'-diamenoketones之间和各种环己二酮和醌导致吡啶并[2,3,4-仿生反应（例如犬尿胺，犬尿氨酸或邻，邻'二氨基二）KL）吖啶类进行说明。几个二-和四氢吡啶并[2,3,4-合成KL）吖啶衍生物（7，10 12和15海洋生物碱）以及benzoderivatives eilatin（1）和ascididemin（2），化合物28和30，已经完成。此外，新的杂环异构体（24）和重氮并五苯19也已经合成。所有新制备的杂环均已通过IR，MS以及主要通过NMR光谱进行了全面表征。已经开发了吡咯并[2,3,4- kl）ac啶的类似合成物，吡咯并[2,3,4- kl ] ac啶是生物活性海洋生物碱的杂环核素（平素）（31 AC）。
• Mononuclear and Dinuclear Complexes of Isoeilatin
  作者：Sheba D. Bergman、Israel Goldberg、Andrea Barbieri、Moshe Kol

  DOI：10.1021/ic050002q

  日期：2005.4.1

  isoeilatin ligand. Coordination of a second metal fragment does not hinder the pi-stacking completely, as demonstrated by the concentration dependence of the 1H NMR spectra of the dinuclear complexes [Ru(bpy)2}2mu-ieil}]4+ (4(4+)), [Os(bpy)2}2mu-ieil}]4+ (5(4+)), and [Ru(bpy)2}mu-ieil}Os(bpy)2}]4+ (6(4+)) and supported by the solid-state structure of meso-4.[Cl]4. The bridging isoeilatin ligand conserves

  这项工作描述了基于对称桥联配体isoeilatin（1）的单核和双核Ru（II）和Os（II）配合物的合成和表征。1. [HCl] 2的晶体结构由双质子化异亮氨酸的紧密π堆积分子层组成。单核络合物[Ru（bpy）2（ieil）] 2+（2（2+））和[Os（bpy）2（ieil）] 2+（3（2+））在分散的二聚体中形成通过异亮氨酸配体的面部选择性pi堆积相互作用。第二种金属片段的配位不会完全阻碍pi堆积，如双核配合物[Ru（bpy）2} 2 mu-ieil}] 4+（4（ 4 +）），[Os（bpy）2} 2 mu-ieil}] 4+（5（4+））和[Ru（bpy）2} mu-ieil} Os（bpy）2 }] 4+（6（4+）），并由meso-4。[Cl] 4的固态结构支撑。桥连的异亮素配体即使在第二个金属片段配位时也能保持其平面性，如meso-4。[Cl] 4，meso-4。[PF6]
• From Eilatin to Isoeilatin:  A Skeletal Rearrangement Strongly Influences π-Stacking of Ru(II) Complex
  作者：Sheba D. Bergman、Dvora Reshef、Limor Frish、Yoram Cohen、Israel Goldberg、Moshe Kol

  DOI：10.1021/ic049806g

  日期：2004.6.28

  The Cl-symmetrical complex [Ru(bpy)(2)(ieil)][PF6](2) exhibits unique electrochemical and photophysical properties, and forms discrete dimers in solution and in the solid state held by weak stacking interactions via its isoeilatin ligand, preferentially from one of its faces and in a specific orientation.
• π-Stacking Induced NMR Spectrum Splitting in Enantiomerically Enriched Ru(II) Complexes:  Evaluation of Enantiomeric Excess
  作者：Sheba D. Bergman、Moshe Kol

  DOI：10.1021/ic048569e

  日期：2005.3.21

  Several chiral octahedral complexes of the general formula [Ru(bpy)(2)(Lig)][PF6](2) (Lig = a ligand that can participate in pi-stacking interactions such as eilatin, isoeilatin, and tpphz) were synthesized in both the racemic and enantiomerically pure/enriched forms. Nonracemic mixtures of enantiomers of all these complexes exhibit splitting of the H-1 NMR spectra (NMR nonequivalence); i.e., each spectrum contains a major and a minor set of peaks. The origin of this phenomenon is attributed to a fast equilibrium between monomers and discrete dimers held together by pi-stacking interactions, and it is observed for a wide range of pi-stacking interaction strengths. The NMR spectrum splitting exhibited by these complexes can be exploited for the evaluation of their enantiomeric excess simply from the integral ratio, without addition of chiral shift reagents.
• A divergent approach to the total synthesis of the marine pyridoacridine alkaloid eilatin and its synthetic isomer isoeilatin
  作者：Alois Plodek、Franz Bracher

  DOI：10.1016/j.tetlet.2015.01.176

  日期：2015.3

  Herein we report the total synthesis of the heptacyclic pyridoacridine alkaloid eilatin (1) and its synthetic isomer isoeilatin (2). Starting from readily available 9-methyl-3,4-dihydroacridin-1(2H)-one (5) and 2-aminoacetophenone, a divergent synthesis gave alkaloid 1 in seven, and isomer 2 in eight steps.

  在本文中，我们报道了七环吡啶并r啶生物碱角蛋白（1）及其合成异构体异角蛋白（2）的总合成。从容易获得的9-甲基-3,4-二氢ac啶-1-1（2 H）-一（5）和2-氨基苯乙酮开始，发散合成得到七分之一的生物碱1和八分之一的异构体2。