benzo[f]indole | 268-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzo[f]indole
• 英文别名: Benz[f]indole；1H-benzo[f]indole；1H-Benz[f]indol；1h-Benzo[f]indole
• CAS: 268-58-6
• 化学式: C₁₂H₉N
• 分子量: 167.21
• InChiKey: FLJIWUNZRZLSME-UHFFFAOYSA-N

物化性质

• 沸点：
  371.1±11.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)
• 熔点：
  190-192 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 储存条件：
  存放于惰性气体中，避免接触空气。

反应信息

• 作为反应物：
  描述：

  benzo[f]indole 在 4-二甲氨基吡啶 、 乙酸酐 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 11.0h， 生成 tert-butyl 3-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-benzo[f]indole-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.028
• 作为产物：
  描述：

  2-氨基-3-溴萘 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 benzo[f]indole
  参考文献：
  名称：

  Sakamoto, Takao; Kondo, Yoshinori; Yamanaka, Hiroshi, Heterocycles, 1986, vol. 24, # 7, p. 1845 - 1847

  摘要：

  DOI：

文献信息

• REACTIVE CYANINE COMPOUNDS
  申请人：Corona Cesear

  公开号：US20110053162A1

  公开（公告）日：2011-03-03

  The invention provides compounds and compositions of Formulas I-VII, and methods of using the compounds. The compounds can be used to prepare dye conjugates that are uniformly and substantially more fluorescent on proteins, nucleic acids or other biopolymers, than conjugates labeled with structurally similar known carbocyanine dyes. In addition to having more intense fluorescence emission than structurally similar dyes at virtually identical wavelengths, and decreased artifacts in their absorption spectra upon conjugation to biopolymers, the compounds can have greater photostability and/or higher absorbance (extinction coefficients) at the wavelength(s) of peak absorbance than such structurally similar dyes.

  该发明提供了公式I-VII的化合物和组合物，以及使用这些化合物的方法。这些化合物可用于制备染料共轭物，其在蛋白质、核酸或其他生物聚合物上比使用结构类似已知碳氰染料标记的共轭物具有更均匀和明显更荧光。除了在几乎相同波长下比结构类似染料具有更强的荧光发射外，并且在与生物聚合物结合时吸收光谱中的伪迹减少，这些化合物在吸收峰波长处可能具有更高的光稳定性和/或更高的吸光度（消光系数）比这些结构类似的染料。
• Indoline compounds and to pharmaceutical compositions containing them
  申请人：——

  公开号：US20030199555A1

  公开（公告）日：2003-10-23

  A compound of formula (I): 1 wherein: R 1 and R 2 together form a benzo ring optionally substituted by halogen or by alkyl, alkoxy, cyano, nitro, hydroxy, amino, alkylamino, dialkylamino or trifluoromethyl, and R 3 represents hydrogen, or R 1 represents hydrogen, and R 2 and R 3 together form a benzo ring optionally substituted by halogen or by alkyl, alkoxy, cyano, nitro, hydroxy, amino, alkylamino, dialkylamino or trifluoromethyl, its enantiomers, diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicaments.

  式（I）的化合物：其中：R1和R2一起形成一个苯环，该苯环可以选择性地被卤素或烷基、烷氧基、氰基、硝基、羟基、氨基、烷基氨基、二烷基氨基或三氟甲基取代，而R3代表氢，或者R1代表氢，而R2和R3一起形成一个苯环，该苯环可以选择性地被卤素或烷基、烷氧基、氰基、硝基、羟基、氨基、烷基氨基、二烷基氨基或三氟甲基取代，其对映体、非对映体异构体以及其与药学上可接受的酸或碱形成的加合物，以及药物。
• Benzoindoline compounds
  申请人：Lavielle Gilbert

  公开号：US20050059675A1

  公开（公告）日：2005-03-17

  A compound of formula (I): wherein: R 1 and R 2 together form a benzo ring optionally substituted by halogen or by alkyl, alkoxy, cyano, nitro, hydroxy, amino, alkylamino, dialkylamino or trifluoromethyl, and R 3 and R 4 represent hydrogen, or R 1 and R 4 represent hydrogen and R 2 and R 3 together form a benzo ring optionally substituted by halogen or by alkyl, alkoxy, cyano, nitro, hydroxy, amino, alkylamino, dialkylamino or trifluoromethyl, or R 1 and R 2 represent hydrogen and R 3 and R 4 together form a benzo ring optionally substituted by halogen or by alkyl, alkoxy, cyano, nitro, hydroxy, amino, alkylamino, dialkylamino or trifluoromethyl, addition salts thereof with a pharmaceutically acceptable acid or base, and methods of treating conditions susceptible to α 2 -AR/5-HT 2C antagonists.

  式(I)的化合物：其中：R1和R2一起形成一个苯环，可以选择地由卤素或烷基、烷氧基、氰基、硝基、羟基、氨基、烷基氨基、二烷基氨基或三氟甲基取代，而R3和R4代表氢，或者R1和R4代表氢，R2和R3一起形成一个苯环，可以选择地由卤素或烷基、烷氧基、氰基、硝基、羟基、氨基、烷基氨基、二烷基氨基或三氟甲基取代，或者R1和R2代表氢，R3和R4一起形成一个苯环，可以选择地由卤素或烷基、烷氧基、氰基、硝基、羟基、氨基、烷基氨基、二烷基氨基或三氟甲基取代，以及它们与药用酸或碱形成的加合物，以及治疗对α2-AR/5-HT2C拮抗剂敏感的疾病的方法。
• Ruthenium‐Catalyzed Vinylene Carbonate Annulation by C−H/N−H Functionalizations: Step‐Economical Access to Indoles
  作者：Yao Yu、Yang Wang、Bo Li、Yuqiang Tan、Huan Zhao、Zheyu Li、Chunran Zhang、Wenbo Ma

  DOI：10.1002/adsc.202101466

  日期：2022.2.15

  A convenient and effective method of ruthenium-catalyzed C−H/N−H annulations using vinylene carbonate as oxidizing acetylene surrogate has been disclosed. This method is scalable and compatible with a wide range of functional groups, providing a step-economical access to indole synthesis Preliminary mechanistic studies provided support for a reversible, acetate-assisted C−H ruthenation, along with

  已经公开了一种使用碳酸亚乙烯酯作为氧化乙炔替代物的钌催化 C-H/N-H 环化的方便有效的方法。该方法具有可扩展性并且与广泛的官能团兼容，为吲哚合成提供了一种经济的方法。初步机理研究为可逆的、乙酸盐辅助的 C-H 钌化以及随后的烯烃插入提供了支持。
• 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...