2-(phenylimino)acenaphthylen-1(2H)-one | 83165-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(phenylimino)acenaphthylen-1(2H)-one
• 英文别名: [N-(phenyl)imino]acenapthenone；BIAO；2-Phenylimino-2H-acenaphthylen-1-one；2-phenyliminoacenaphthylen-1-one
• CAS: 83165-56-4
• 化学式: C₁₈H₁₁NO
• 分子量: 257.291
• InChiKey: OYZOQOOSEDTSFN-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C
• 沸点：
  476.0±28.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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-(phenylimino)acenaphthylen-1(2H)-one 在 sodium cyanide 、 氧气 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以84%的产率得到2-phenylbenzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Reduction of 1,2-dicarbonyl compounds and of their N-phenylimine derivatives by sodium cyanide under aprotic conditions

  摘要：

  摘要 一些芳香性1,2-二羰基化合物，即9,10-菲南酮、萘并醌和苯基乙酮及其相应的N-苯基单亚胺，已在存在氰化钠作为还原剂的情况下，使用干燥的乙腈作为溶剂进行还原。文中描述了比较静电测量法的制备规模电解。

  DOI：

  10.1016/j.crci.2015.07.007

文献信息

• Electronic Structure and Multicatalytic Features of Redox-Active Bis(arylimino)acenaphthene (BIAN)-Derived Ruthenium Complexes
  作者：Arijit Singha Hazari、Ritwika Ray、Md Asmaul Hoque、Goutam Kumar Lahiri

  DOI：10.1021/acs.inorgchem.6b01280

  日期：2016.8.15

  The article examines the newly designed and structurally characterized redox-active BIAN-derived [Ru(trpy)(R-BIAN)Cl]ClO4 ([1a]ClO4–[1c]ClO4), [Ru(trpy)(R-BIAN)(H2O)](ClO4)2 ([3a](ClO4)2–[3c](ClO4)2), and BIAO-derived [Ru(trpy)(BIAO)Cl]ClO4 ([2a]ClO4) (trpy = 2,2′:6′,2′′-terpyridine, R-BIAN = bis(arylimino)acenaphthene (R = H (1a+, 3a2+), 4-OMe (1b+, 3b2+), 4-NO2 (1c+, 3c2+), BIAO = [N-(phenyl)imino]acenapthenone)

  本文研究了新设计和结构表征的氧化还原活性的BIAN衍生的[Ru（trpy）（R-BIAN）Cl] ClO 4（[ 1a ] ClO 4 – [ 1c ] ClO 4），[Ru（trpy）（R -BIAN）（H 2 O）]（ClO 4）2（[ 3a ]（ClO 4）2 – [ 3c ]（ClO 4）2）和BIAO衍生的[Ru（trpy）（BIAO）Cl] ClO 4（[ 2a ] ClO 4）（trpy = 2,2'：6'，2'-terpyridine，R-BIAN =双（芳基）ac啶（R = H（1a +，3a 2+），4-OMe（1b +，3b 2 +），4-NO 2（1c +，3c 2 +），BIAO = [ N-（苯基）亚氨基] ac庚烯）。1 a n – 1c n或2a n的实验（X射线，1 H NMR，光谱电化学，EPR）和DFT / TD-DFT计算共同建立了Ru II –BIAN
• Tunable Electrochemical and Catalytic Features of BIAN- and BIAO-Derived Ruthenium Complexes
  作者：Arijit Singha Hazari、Ankita Das、Ritwika Ray、Hemlata Agarwala、Somnath Maji、Shaikh M. Mobin、Goutam Kumar Lahiri

  DOI：10.1021/acs.inorgchem.5b00615

  日期：2015.5.18

  This article deals with a class of ruthenium-BIAN-derived complexes, [Ru-II(tpm)(R-BIAN)Cl]ClO4 (tpm = tris(1-pyrazolyl)methane, R-BIAN = bis(arylimino)acenaphthene, R = 4-OMe ([1a]ClO4), 4-F ([1b]ClO4), 4-Cl ([1c]ClO4), 4-NO2 ([1d]ClO4)) and [Ru-II(tpm)(OMe-BIAN)H2O](2+) ([3a](ClO4)2). The R-BIAN framework with R = H, however, leads to the selective formation of partially hydrolyzed BIAO ([N-(phenyl)imino]acenapthenone)-derived complex [Ru-II(tpm)(BIAO)Cl]ClO4 ([2]ClO4). The redox-sensitive bond parameters involving -N=C-C=N- or -N=C-C=O of BIAN or BIAO in the crystals of representative [1a]ClO4, [3a](PF6)(2), or [2]ClO4 establish its unreduced form. The chloro derivatives 1a(+)-1d(+) and 2(+) exhibit one oxidation and successive reduction processes in CH3CN within the potential limit of +/- 2.0 V versus SCE, and the redox potentials follow the order 1a(+) < 1b(+) < 1c(+) < 1d(+) approximate to 2(+). The electronic structural aspects of 1a(n)-1d(n) and 2(n) (n = +2, +1, 0, -1, -2, -3) have been assessed by UV-vis and EPR spectroelectrochemistry, DFT-calculated MO compositions, and Mulliken spin density distributions in paramagnetic intermediate states which reveal metal-based (Ru-II -> Ru-III) oxidation and primarily BIAN- or BIAO-based successive reduction processes. The aqua complex 3a(2+) undergoes two proton-coupled redox processes at 0.56 and 0.85 V versus SCE in phosphate buffer (pH 7) corresponding to Ru-II-H2O}/Ru-III-OH} and Ru-III-OH}/Ru-IV=O}, respectively. The chloro (1a(+)-1d(+)) and aqua (3a(2+)) derivatives are found to be equally active in functioning as efficient precatalysts toward the epoxidation of a wide variety of alkenes in the presence of PhI(OAc)(2) as oxidant in CH2Cl2 at 298 K, though the analogous 2(+) remains virtually inactive. The detailed experimental analysis with the representative precatalyst 1a(+) suggests the involvement of the active Ru-IV=O} species in the catalytic cycle, and the reaction proceeds through the radical mechanism, as also supported by the DFT calculations.
• Reduction of 1,2-dicarbonyl compounds and of their N-phenylimine derivatives by sodium cyanide under aprotic conditions
  作者：Kaouthar Hamrouni、Belen Batanero、Fructuoso Barba、Isidoro Barba、Khaled Boujlel、Mohamed Lamine Benkhoud

  DOI：10.1016/j.crci.2015.07.007

  日期：2015.12

  Résumé Some aromatic 1,2-dicarbonyl compounds, i.e. 9,10-phenanthrenequinone, acenaphthenequinone and benzil, and their corresponding N-phenyl monoimines, have been reduced, using dry acetonitrile as the solvent, in the presence of sodium cyanide as a reducing agent. Comparative potentiostatic preparative-scale electrolysis is described.

  摘要 一些芳香性1,2-二羰基化合物，即9,10-菲南酮、萘并醌和苯基乙酮及其相应的N-苯基单亚胺，已在存在氰化钠作为还原剂的情况下，使用干燥的乙腈作为溶剂进行还原。文中描述了比较静电测量法的制备规模电解。