1-(5-氯-1H-吲哚-3-基)乙酮 | 51843-24-4

• 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
• 中文名称: 1-(5-氯-1H-吲哚-3-基)乙酮
• 中文别名: 5-氯-3吲哚乙铜；3-乙酰基-5-氯吲哚
• 英文名称: 3-acetyl-5-chloro-1H-indole
• 英文别名: 1-(5-chloro-1H-indol-3-yl)ethan-1-one；1-(5-chloro-1H-indol-3-yl)ethanone
• CAS: 51843-24-4
• 化学式: C₁₀H₈ClNO
• 分子量: 193.633
• InChiKey: LEUBXJIHEAWOHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C (decomp)(Solv: ethyl ether (60-29-7))
• 沸点：
  367.9±22.0 °C(Predicted)
• 密度：
  1.332

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  1-(5-氯-1H-吲哚-3-基)乙酮 在 盐酸 、 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 tert-butyl N-[(2S)-1-[[(1S)-2-[(2S)-2-[(3-acetyl-5-chloroindol-1-yl)methyl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino]-1-oxopropan-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  COMBINATION OF IAP INHIBITOR AND IMMUNE CHECKPOINT INHIBITOR

  摘要：

  本发明涉及一种由式(I)所表示的化合物、其异构体或其药学上可接受的盐的组合物，其用作IAP抑制剂，以及免疫检查点抑制剂的组合物；以及该组合物在制备癌症治疗药物中的应用。

  公开号：

  US20220175917A1
• 作为产物：
  描述：

  5-氯吲哚-2-羧酸 在 喹啉 、 铜 、 溶剂黄146 作用下， 反应 23.0h， 生成 1-(5-氯-1H-吲哚-3-基)乙酮
  参考文献：
  名称：

  Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives in vitro

  摘要：

  A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 x 10(3)- and 2.0 x 10(3)- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 mu M), respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.055

文献信息

• Towards the syntheses of<i>N</i>-H and<i>N</i>-alkylated derivatives of meridianins
  作者：Bernard Corbel、FrançOis Michaud、Laurent Meijer、Gaëlle Simon、Hélène Couthon-Gourves、Jean-Pierre Haelters、Nelly Kervarec

  DOI：10.1002/jhet.5570440407

  日期：2007.7

  Novel N-H and N-alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two-step conversion of N-tosyl-3-acetylindoles or N-alkyl-3-acetylindoles to the corresponding enaminones using DMF-DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2-aminopyrimidines. The structures of the compounds, thus obtained, were proved

  通过使用DMF-DMA将N-甲苯磺酰基-3-乙酰基吲哚或N-烷基-3-乙酰基吲哚经两步转化为相应的烯胺酮，合成了经络胺的新型N- H和N-烷基化衍生物作为潜在的抗肿瘤药。或不添加吡咯烷。用胍进一步环化得到相应的2-氨基嘧啶。由此获得的化合物的结构通过1 H和13 C NMR光谱，NOE实验和X射线分析证明。
• A Simple, Effective, Green Method for the Regioselective 3-Acylation of Unprotected Indoles
  作者：Phuong Tran、Hai Tran、Poul Hansen、Mai Do、Thach Le

  DOI：10.3390/molecules201019605

  日期：——

  A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.

  开发了一种快速且绿色方法，用于吲哚3-位选择性酰化而无需保护NH位置。该方法基于使用酸酐的Friedel-Crafts酰化反应。经过优化，发现使用催化量的Y(OTf)3和市售离子液体[BMI]BF4(1-丁基-3-甲基咪唑四氟硼酸盐)作为溶剂效果最佳。反应在单模微波辐射下非常短的时间内完成。该催化剂可重复使用多达四次而不会明显损失活性。研究了一系列取代吲哚作为底物，并合成了十三种新化合物。
• Brønsted acidic ionic liquid-promoted direct C3-acylation of <i>N</i>-unsubstituted indoles with acid anhydrides under microwave irradiation
  作者：Phuong Hoang Tran、Anh-Thanh Duy Nguyen、Hai Truong Nguyen、Thach Ngoc Le

  DOI：10.1039/c7ra11362e

  日期：——

  A green and efficient method for the synthesis of 3-acylindoles using a Brønsted acidic ionic liquid under microwave irradiation has been developed.

  使用布朗斯特酸性离子液体在微波辐射下合成3-酰基吲哚的一种绿色高效方法已经开发出来。
• Imidazolium Triflate Ionic Liquid Improves the Activity of ZnCl₂ in the Synthesis of Pyrroles and Ketones
  作者：Hai Truong Nguyen、Dung Kim Thi Ngo、Khiem Duy Nguyen Chau、Phuong Hoang Tran

  DOI：10.1080/00304948.2020.1868910

  日期：2021.3.4

  (2021). Imidazolium Triflate Ionic Liquid Improves the Activity of ZnCl2 in the Synthesis of Pyrroles and Ketones. Organic Preparations and Procedures International: Vol. 53, No. 2, pp. 157-165.

  （2021年）。三氟甲磺酸咪唑鎓离子液体可提高ZnCl2在吡咯和酮合成中的活性。国际有机制剂和程序：Vol。53，第2号，第157-165页。
• Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds To Form Highly Functionalized Carbazoles
  作者：Zhidong Jiang、Jianhui Zhou、Haoran Zhu、Hong Liu、Yu Zhou

  DOI：10.1021/acs.orglett.1c01341

  日期：2021.6.4

  A novel Rh(III)-catalyzed C–H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a novel [5 + 1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-dimethyl groups

  据报道，一种新型 Rh(III) 催化的吲哚-烯胺酮与重氮化合物的 C-H 活化/环化级联可构建多种功能化的咔唑框架。最显着的特点是这种转化可以顺利地提供一种新的 [5 + 1] 环化产物，收率从高到高（高达 95%），同时彻底去除了两种底物的乙酰基和N , N-二甲基基团。目标产物，而不是通常预期的 [4 + 2] 环化产物。