3-Methylbenz[f]indole | 33333-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Methylbenz[f]indole
• 英文别名: 3-methyl-1H-benzo[f]indole
• CAS: 33333-87-8
• 化学式: C₁₃H₁₁N
• 分子量: 181.237
• InChiKey: MUJGIRQUJZFHJR-UHFFFAOYSA-N

物化性质

• 沸点：
  377.7±11.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  苯磺酰氯 、 3-Methylbenz[f]indole 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 lithium diisopropyl amide 作用下， 生成 N-benzenesulfonyl-4-bromo-3-methylbenz[f]indole
  参考文献：
  名称：

  The structures of N-(t-butoxycarbonyl)-3-methylbenz[f]indole and N-benzenesulfonyl-4-bromo-3-methylbenz[f]indole

  摘要：

  N-(t-butoxycarbonyl)-3-methylbenz[f]indole, 1, C18H19NO2, crystallizes in orthorhombic space group Pna2(1) with a = 6.0338(2), b = 24.839(4), c = 10.2481(7) Angstrom, V = 1535.9(3) Angstrom 3, Z = 4. The structure was refined to R = 0.051 for 2007 observed reflections. The benz[f]indole ring system is nearly planar, exhibiting mean deviation of 0.048 Angstrom. The ester plane of the t-butoxycarbonyl substituent is nearly coplanar with the benz[f]indole ring system, forming a C-N-C=O torsion angle with magnitude 10.6(5)degrees. N-benzenesulfonyl-4-bromo-3-methyl-benz[f]indole, 2, C19H14BrNO2S crystallizes in triclinic space group P (1) over bar with a = 8.1400(5), b = 10.0587(8), c = 10.8863(7) Angstrom, alpha = 89.927(7), beta = 110.495(5), gamma = 96.846(6)degrees, V = 828.2(3) Angstrom(3), Z = 2. The structure was refined to R = 0.050 for 2653 observed reflections. The benz[f]indole ring system is nearly planar, with mean deviation 0.016 Angstrom, and forms a dihedral angle of 80.93(9)degrees with the phenyl plane.

  DOI：

  10.1007/bf02575962
• 作为产物：
  描述：

  1-(三甲基硅基)丙炔 、 2-氨基-3-溴萘 在 palladium diacetate 四丁基氯化铵 、 sodium carbonate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以80.8%的产率得到3-Methylbenz[f]indole
  参考文献：
  名称：

  Benz[f]indole 的荧光特性，一种波长和猝灭选择性色氨酸类似物

  摘要：

  具有独特光谱和光物理特性的色氨酸类似物为研究肽-蛋白质和蛋白质-蛋白质相互作用提供了内在的荧光探针。合成了两种苯并环吲哚衍生物苯并[f]吲哚和3-甲基苯并[f]吲哚，并对其荧光进行了表征。吸收和荧光发射光谱红移约 75 nm 至吲哚和 3-甲基吲哚光谱的红色。INDO/S-CIS 计算表明两个几乎退化的最低激发单重态，类似于吲哚的 1La 和 1Lb 跃迁，但具有几乎共线的跃迁矩。随着波长的增加，极限激发各向异性光谱增加，发射各向异性光谱减少，这可能是由于 1La 状态与更高能量 B 状态的振动耦合。溶剂和温度对最大发射波长的影响认为发射发生在极地环境中的 1La 中。荧光量子产率和寿命很高，而且很...

  DOI：

  10.1021/jp9925536

文献信息

• CARBOXYLIC ACID DERIVATIVES AS HIV REPLICATION INHIBITOR
  申请人：Shionogi & Co., Ltd.

  公开号：EP2952503B1

  公开（公告）日：2019-10-23
• Fluorescence Properties of Benz[<i>f</i>]indole, a Wavelength and Quenching Selective Tryptophan Analog
  作者：Bo Liu、Mary D. Barkley、Guillermo A. Morales、Mark L. McLaughlin、Patrik R. Callis

  DOI：10.1021/jp9925536

  日期：2000.3.1

  benzannulated indole derivatives, benz[f]indole and 3-methylbenz[f]indole, were synthesized and their fluorescence was characterized. The absorption and fluorescence emission spectra are red shifted about 75 nm to the red of the spectra of indole and 3-methylindole. INDO/S−CIS computations indicate two nearly degenerate lowest excited singlet states, analogous to the 1La and 1Lb transitions of indoles but with

  具有独特光谱和光物理特性的色氨酸类似物为研究肽-蛋白质和蛋白质-蛋白质相互作用提供了内在的荧光探针。合成了两种苯并环吲哚衍生物苯并[f]吲哚和3-甲基苯并[f]吲哚，并对其荧光进行了表征。吸收和荧光发射光谱红移约 75 nm 至吲哚和 3-甲基吲哚光谱的红色。INDO/S-CIS 计算表明两个几乎退化的最低激发单重态，类似于吲哚的 1La 和 1Lb 跃迁，但具有几乎共线的跃迁矩。随着波长的增加，极限激发各向异性光谱增加，发射各向异性光谱减少，这可能是由于 1La 状态与更高能量 B 状态的振动耦合。溶剂和温度对最大发射波长的影响认为发射发生在极地环境中的 1La 中。荧光量子产率和寿命很高，而且很...
• The structures of N-(t-butoxycarbonyl)-3-methylbenz[f]indole and N-benzenesulfonyl-4-bromo-3-methylbenz[f]indole
  作者：T. Scott Yokum、Guillermo A. Morales、Ted J. Gauthier、Frank R. Fronczek

  DOI：10.1007/bf02575962

  日期：1997.4

  N-(t-butoxycarbonyl)-3-methylbenz[f]indole, 1, C18H19NO2, crystallizes in orthorhombic space group Pna2(1) with a = 6.0338(2), b = 24.839(4), c = 10.2481(7) Angstrom, V = 1535.9(3) Angstrom 3, Z = 4. The structure was refined to R = 0.051 for 2007 observed reflections. The benz[f]indole ring system is nearly planar, exhibiting mean deviation of 0.048 Angstrom. The ester plane of the t-butoxycarbonyl substituent is nearly coplanar with the benz[f]indole ring system, forming a C-N-C=O torsion angle with magnitude 10.6(5)degrees. N-benzenesulfonyl-4-bromo-3-methyl-benz[f]indole, 2, C19H14BrNO2S crystallizes in triclinic space group P (1) over bar with a = 8.1400(5), b = 10.0587(8), c = 10.8863(7) Angstrom, alpha = 89.927(7), beta = 110.495(5), gamma = 96.846(6)degrees, V = 828.2(3) Angstrom(3), Z = 2. The structure was refined to R = 0.050 for 2653 observed reflections. The benz[f]indole ring system is nearly planar, with mean deviation 0.016 Angstrom, and forms a dihedral angle of 80.93(9)degrees with the phenyl plane.