4-(1H-indol-2-yl)phenol | 40643-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(1H-indol-2-yl)phenol
• 英文别名: 2-(4'-hydroxy-phenyl)-indole
• CAS: 40643-14-9
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: BQWAJIFVKAXHCO-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  441.0±20.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(1H-indol-2-yl)phenol 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-{[2-(4-hydroxyphenyl)-1H-indol-3-yl]methylene}hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives

  摘要：

  The starting material, 4-(1-indol-2-yl)phenol 1 was obtained via Fischer synthesis. Vilsmeir Haack's formylation of 1 gave the carboxaldehyde derivative 2 which was subjected to different reactions affording the 3-substituted compounds 3-10. Compound 1 reacted with halo esters to give 11 and 12a,b. The reaction of 12a with various amino derivatives gave compounds 13-16. The hydrazide derivative 15a reacted with 1,3-diketones, ethyl acetoacetate and aromatic carboxylic acid derivatives to give 17a,b, 18 and 19a-e, respectively. Antitumor activity of target compounds were tested against breast cancer cell lines (MCF-7) and (MDA-MB-231). The most potent compound was 3e with IC50 = 1.60 nM against (MCF-7). Docking was performed on colchicine binding site of tubulin to study the binding mode of the designed compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.007
• 作为产物：
  描述：

  对羟基苯乙酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 4-(1H-indol-2-yl)phenol
  参考文献：
  名称：

  铁（III）催化吲哚与苄胺的脱氢交叉偶联反应制备3-氨基吲哚衍生物

  摘要：

  我们报告了一种绿色级联方法，通过铁 ( III ) 催化的 2-芳基吲哚和伯苄胺在温和反应条件下的脱氢交叉偶联反应，以良好到优异的产率制备各种 3-氨基吲哚衍生物。机理研究表明，级联反应涉及亚硝酸叔丁酯 (TBN) 介导的 2-取代吲哚的亚硝化和 1,5-氢转移以提供吲哚啉肟、序贯铁 ( III))-催化缩合和 1,5- 氢转移在一锅反应的四个步骤中。该反应显示了吲哚和苄胺的广泛底物范围，并且可以耐受广泛的官能团。此外，反应很容易以克规模进行，反应完成后不会产生废物。3-氨基吲哚产物通过简单的萃取、洗涤和重结晶纯化，无需快速柱色谱。含有3-氨基吲哚单元的双亚胺配体易于一步获得，产率为52%。本方法突出了容易获得的起始材料、简单的纯化程序以及廉价、无毒和环境友好的铁 ( III ) 催化剂的使用。

  DOI：

  10.1039/d1gc02849a

文献信息

• 2-Phenyl-indole derivatives and process for preparing the same
  申请人：Labaz

  公开号：US04057530A1

  公开（公告）日：1977-11-08

  New stabilizers of polymers and co-polymers of vinyl chloride, the said stabilizers being 2-phenyl-indole derivatives corresponding to the formula: ##STR1## wherein R represents a phenyl radical, an amino group, optionally substituted by an acetyl or benzoyl radical, a mercapto group, optionally substituted by a branched-or straight-chain alkyl group containing from 1 to 12 carbon atoms or by a cyclohexyl radical, a carboxyl radical, a radical represented by the formula: R.sub.1 O-- wherein R.sub.1 represents a hydrogen atom, an isopropyl, carboxymethyl, carbethoxymethyl, carbethoxyisopropyl, acetyl, docosanoyl, benzoyl, benzyl, or allyl radical or a branched-or straight-chain alkyl radical containing from 6 to 12 carbon atoms.

  新型稳定剂用于聚合物和氯乙烯共聚物，所述稳定剂为与下式对应的2-苯基吲哚衍生物：##STR1## 其中R代表苯基基团，氨基团，可选地由乙酰基或苯甲酰基取代，巯基，可选地由含有1至12个碳原子的支链或直链烷基基团或环己基基团取代，羧基基团，由下式表示的基团：R.sub.1 O--其中R.sub.1代表氢原子，异丙基，羧甲基，羧乙氧甲基，羧乙氧异丙基，乙酰基，二十二烷酰基，苯甲酰基，苄基或烯丙基基团或含有6至12个碳原子的支链或直链烷基基团。
• Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives
  作者：Zohreh Bakherad、Maliheh Safavi、Afshin Fassihi、Hojjat Sadeghi-Aliabadi、Mohammad Bakherad、Hossein Rastegar、Jahan B. Ghasemi、Saghi Sepehri、Lotfollah Saghaie、Mohammad Mahdavi

  DOI：10.1007/s11164-019-03765-9

  日期：2019.5

  Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630 µM, comparable to the standard ascorbic acid (0.655 µM).

  基于生物活性3-取代吲哚的结构元素，设计、合成了新一系列吲哚-缩氨硫脲杂化衍生物，并利用不同光谱技术对其进行了很好的表征。对这些预期的支架结构进行了体外抗增殖活性筛选，针对乳腺癌（MCF-7）、肺癌（A-549）和肝癌（Hep-G2）细胞系，以及它们的抗氧化性能。细胞毒性研究表明，化合物6n对A-549的活性最强，至少是市售参考药物依托泊苷的三倍。此外，通过吖啶橙/溴化乙锭双重染色试验和流式细胞术分析，确认化合物6n诱导A-549细胞凋亡。为了验证实验结果，进行了分子研究，以实现最强化合物（6n）和秋水仙碱与微管蛋白的可能结合相互作用，以及ANP与拓扑异构酶IIα的ATP酶域活性位点的相互作用。此外，最终衍生物的自由基清除潜力非常出色，范围为0.015-0.630 µM，与标准抗坏血酸（0.655 µM）相当。
• Indium-Catalyzed Annulation of 2-Aryl- and 2-Heteroarylindoles with Propargyl Ethers: Concise Synthesis and Photophysical Properties of Diverse Aryl- and Heteroaryl-Annulated[<i>a</i>]carbazoles
  作者：Teruhisa Tsuchimoto、Hiromichi Matsubayashi、Masayoshi Kaneko、Yuta Nagase、Takuhiro Miyamura、Eiji Shirakawa

  DOI：10.1021/ja803954e

  日期：2008.11.26

  is applicable also to symmetrical dimers such as bithiophene and bifuran derivatives. Mechanistic studies suggest that the first step is addition reaction initiated by regioselective nucleophilic attack of the C3 of 2-aryl- and 2-heteroarylindoles to the internal carbon atom of the C[triple bond]C bond in propargyl ethers. The next stage is ring-closing S(N)2 process kicking out the alkoxy group and

  在催化量的九氟丁烷磺酸铟 [In(ONf)(3)] 存在下，用炔丙基醚处理 2-芳基-和 2-杂芳基吲哚，以良好的产率得到芳基-和杂芳基-环化的 [a] 咔唑。合成上有吸引力的特征反映在其对广泛范围的 2-芳基-和 2-杂芳基吲哚的适用性上。在环化反应中，炔丙醚作为 C3 源（HC[三键]C-CH(2)OR）。其中，两个碳原子作为新构建的芳环的成员并入产物中，剩余的碳原子在芳环上形成甲基，其中甲基始终位于吲哚核的 C3 位置旁边。甲基可以通过 SeO(2) 氧化轻松去除，然后用 RhCl(CO)(PPh(3))(2)-Ph(2)P(CH(2))(3)PPh(2) 脱羰，如一种催化剂。新的环化策略也适用于对称二聚体，如联噻吩和双呋喃衍生物。机理研究表明，第一步是通过 2-芳基-和 2-杂芳基吲哚的 C3 与炔丙醚中 C[三键]C 键的内部碳原子的区域选择性亲核攻击引发的加成反应。下一阶段是闭环
• TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2-<i>a</i>]pyridines with Fluorinated Alcohols
  作者：Dhananjay S. Nipate、Sonam Jaspal、Vikki N. Shinde、Krishnan Rangan、Anil Kumar

  DOI：10.1021/acs.orglett.1c00031

  日期：2021.2.19

  A simple and highly efficient metal-free method has been developed for hydroxyfluoroalkylation of indoles and imidazo[1,2-a]pyridines via TEMPO-mediated C(sp3)–H and C(sp2)–H bond cross-dehydrogenative coupling of fluorinated alcohols and indoles. The protocol showed broad substrate scope, afforded good yields of hydroxyfluoroalkylated products, and was amenable for scale-up. Mechanistic investigation

  已经开发了一种简单高效的无金属方法，用于通过TEMPO介导的C（sp 3）–H和C（sp 2）–H键交叉脱氢偶联将吲哚和咪唑并[1,2- a ]吡啶进行羟基氟烷基化氟化醇和吲哚。该方案显示出广泛的底物范围，提供了良好的羟基氟烷基化产物收率，并且适合规模扩大。机理研究表明该自由基途径的参与。
• Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
  作者：Kai Yang、Yixian Lou、Chenglan Wang、Liang‐Wen Qi、Tongchang Fang、Feng Zhang、Hetao Xu、Lu Zhou、Wangyang Li、Guan Zhang、Peiyuan Yu、Qiuling Song

  DOI：10.1002/anie.201913656

  日期：2020.2.17

  A new chiral Brønsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This "designer acid catalyst", which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities

  由手性磷酸硼（CPAB）配合物和水原位生成的新手性布朗斯台德酸已成功地用于不对称吲哚还原。如DFT计算所建议的，这种“设计酸催化剂”比TsOH酸性更强，可实现C2-芳基取代的N-未保护的吲哚空前的直接不对称还原，并具有良好的对映选择性，并具有宽泛的官能团耐受性。DFT计算和机理实验表明该反应经历了C3质子化和氢化物转移过程。此外，庞大的C 2-烷基取代的N-未保护的吲哚也适用于该体系。