dihydro-11H-indeno[2,1-a]pyren-11-one | 7267-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: dihydro-11H-indeno[2,1-a]pyren-11-one
• 英文别名: 11H-indeno[2,1-a]-pyren-11-one；11H-indeno[2,1-a]pyren-11-one；indeno[2,1-a]pyren-11-one；Indeno[2,1-a]pyren-11-on；11H-Indeno(2,1-A)pyren-11-one；hexacyclo[13.6.2.02,10.04,9.012,22.019,23]tricosa-1(22),2(10),4,6,8,11,13,15(23),16,18,20-undecaen-3-one
• CAS: 7267-90-5
• 化学式: C₂₃H₁₂O
• 分子量: 304.348
• InChiKey: CIXQFTJGIONQCO-UHFFFAOYSA-N

物化性质

• 沸点：
  548.8±17.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dihydro-11H-indeno[2,1-a]pyren-11-one 在 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 生成 11H-Indeno-<2.1-a>pyren
  参考文献：
  名称：

  Intramolecular Charge Transfer (ICT) and Solvation of a Rigidly Linked Pyrene/N-Methylindolino Derivative and Related Compounds in Linear Alcohols

  摘要：

  Measurements on a rather rigid and coplanar bichromophoric compound have been carried out with respect to intramolecular charge separation, as well as regarding solvation and lifetime of the CT state in alcohol solutions. The results indicate that the CT step proceeds very efficiently followed by a Stokes shift of the CT emission band governed by the dielectric relaxation of the solvent (a series of n-alcohols), The average Stokes-shift time, tau(solv) (of a few hundred picoseconds), correlates directly with the longitudinal relaxation time, tau(L) = (epsilon(infinity)/epsilon(s))tau(D), of the solvent. The recently developed single-shot spectrostreak picosecond technique was used for the collection of the time-resolved emission spectra.

  DOI：

  10.1021/jp961182f
• 作为产物：
  描述：

  苯甲酰氯 在 aluminum (III) chloride 、 磷酸 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 dihydro-11H-indeno[2,1-a]pyren-11-one
  参考文献：
  名称：

  探索芘系列中 Friedel-Crafts 酰基重排的可逆性

  摘要：

  PPA 中二乙酰芘 (80–120 °C)、二苯甲酰基芘 (80–200 °C) 和双 (4-氟苯甲酰基) 芘 (80–120 °C) 的 Friedel-Crafts 酰基重排和 AlCl 3 /NaCl 中的 Scholl 反应已经研究了二苯甲酰芘（140-200°C）。底物为 1-AcPY、2-AcPY、1,3-Ac 2 PY、1,6-Ac 2 PY、1,8-Ac 2 PY、2,7-Ac 2 PY、1-BzPY、1,6 -Bz 2 PY , 1,8-Bz 2 PY , 1-4FBzPY , 1,6-4FBz 2 PY , 1,8-4FBz 2 PY 。通过HPLC分离芘、1-AcPY、2-AcPY、1,3-Ac 2 PY、1,6-Ac 2 PY、1,8-Ac 2 PY 和2,7-Ac 2 PY 的混合物。建立了以下可逆分子间异构化：1,6-Ac 2 PY ⇌ 1,8-Ac 2 PY 、1

  DOI：

  10.1007/s11224-019-01460-4

文献信息

• Palladium Catalyzed Regioselective Cyclization of Arylcarboxylic Acids via Radical Intermediates with Diaryliodonium Salts
  作者：Guoqiang An、Limin Wang、Jianwei Han

  DOI：10.1021/acs.orglett.1c03016

  日期：2021.11.19

  Palladium-catalyzed C2-arylation/intramolecular acylation with arylcarboxylic acids was developed by using diaryliodonium salts. The protocol has the advantage of good step-economy by two chemical bonds formation in one pot.

  通过使用二芳基碘鎓盐开发了钯催化的 C 2 -芳基化/与芳基羧酸的分子内酰化。该协议的优点是在一锅中形成两个化学键，具有良好的阶梯经济性。
• Regioselectivity in the Controversial Scholl Reaction of 1-Benzoylpyrene: Formation of a Five-Member Ring Is Not Unexpected
  作者：Yaacov Netanel Oded、Sergey Pogodin、Israel Agranat

  DOI：10.1021/acs.joc.6b01798

  日期：2016.11.18

  Intramolecular Scholl reaction of 1-benzoylpyrene (1) gave 8H-dibenzo[def,qr]chrysen-8-one (2) and 11H-indeno[2,1-a]pyren-11-one (3) in a 1:2 ratio. The structures of 2 and 3 were determined, using 1H NMR, 13C NMR, and IR spectroscopies. A DFT B3LYP/6-311G(d,p) study of the reaction’s arenium–cation mechanism of (E)-1 and (Z)-1 giving 2 and 3, respectively, indicated the reaction’s regioselectivity and

  1-苯甲酰py的分子内Scholl反应（1）在a中得到8 H-二苯并[ def，qr ] chrysen-8-one（2）和11 H-茚并[ 2,1- a ] pyren -11-one（3）。 1：2的比例。使用1 H NMR，13 C NMR和IR光谱确定2和3的结构。DFT B3LYP / 6-311G（d，p）研究反应的（E）-1和（Z）-1的芳烃阳离子机理，得到2和3分别表明反应的区域选择性和动力学控制。1-（1'-萘甲酰基）re的类似反应仅给出13 H-苯并[4,5]茚并[ 2,1- a ] -13-13-。与先前的权利要求相反，在Scholl反应中优选形成五元环并不是意料之外的。
• Clar, Chemische Berichte, 1948, vol. 81, p. 520,526
  作者：Clar

  DOI：——

  日期：——
• In quest of reversibility of Friedel-Crafts acyl rearrangements in the pyrene series
  作者：Israel Agranat、Tahani Mala’bi、Yaacov Netanel Oded、Hanna Daniel Kraus

  DOI：10.1007/s11224-019-01460-4

  日期：2020.2

  reaction of reactive aromatic hydrocarbons is a reversible process .” The isomerizations reported here differ from the few previously reported completely reversible intramolecular Friedel-Crafts acyl rearrangements. At ≥ 140 °C, in PPA and in AlCl 3 /NaCl, 1,6-Bz 2 PY and 1,8-Bz 2 PY underwent a highly regioselective double Scholl reaction to give pyranthrone ( 3 ) and deacylations to 1-BzPy (and pyrene)

  PPA 中二乙酰芘 (80–120 °C)、二苯甲酰基芘 (80–200 °C) 和双 (4-氟苯甲酰基) 芘 (80–120 °C) 的 Friedel-Crafts 酰基重排和 AlCl 3 /NaCl 中的 Scholl 反应已经研究了二苯甲酰芘（140-200°C）。底物为 1-AcPY、2-AcPY、1,3-Ac 2 PY、1,6-Ac 2 PY、1,8-Ac 2 PY、2,7-Ac 2 PY、1-BzPY、1,6 -Bz 2 PY , 1,8-Bz 2 PY , 1-4FBzPY , 1,6-4FBz 2 PY , 1,8-4FBz 2 PY 。通过HPLC分离芘、1-AcPY、2-AcPY、1,3-Ac 2 PY、1,6-Ac 2 PY、1,8-Ac 2 PY 和2,7-Ac 2 PY 的混合物。建立了以下可逆分子间异构化：1,6-Ac 2 PY ⇌ 1,8-Ac 2 PY 、1
• Intramolecular Charge Transfer (ICT) and Solvation of a Rigidly Linked Pyrene/<i>N</i>-Methylindolino Derivative and Related Compounds in Linear Alcohols
  作者：A. Wiessner、W. Kühnle、T. Fiebig、H. Staerk

  DOI：10.1021/jp961182f

  日期：1997.1.1

  Measurements on a rather rigid and coplanar bichromophoric compound have been carried out with respect to intramolecular charge separation, as well as regarding solvation and lifetime of the CT state in alcohol solutions. The results indicate that the CT step proceeds very efficiently followed by a Stokes shift of the CT emission band governed by the dielectric relaxation of the solvent (a series of n-alcohols), The average Stokes-shift time, tau(solv) (of a few hundred picoseconds), correlates directly with the longitudinal relaxation time, tau(L) = (epsilon(infinity)/epsilon(s))tau(D), of the solvent. The recently developed single-shot spectrostreak picosecond technique was used for the collection of the time-resolved emission spectra.