7-chloro-5H-indeno[1,2-b]pyridin-5-one | 101419-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-chloro-5H-indeno[1,2-b]pyridin-5-one
• 英文别名: 5H-Indeno[1,2-b]pyridin-5-one, 7-chloro-；7-chloroindeno[1,2-b]pyridin-5-one
• CAS: 101419-81-2
• 化学式: C₁₂H₆ClNO
• 分子量: 215.639
• InChiKey: FXPFSQBEYMGUNM-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C
• 沸点：
  407.3±28.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-5H-indeno[1,2-b]pyridin-5-one 在 盐酸 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-aza-7-chloro-9-hydroxy-9-fluorene carboxylic acid methyl ester
  参考文献：
  名称：

  9-Hydroxyazafluorenes and Their Use in Thrombin Inhibitors

  摘要：

  Optimization of a previously reported thrombin inhibitor, 9-hydroxy-9-fluorenylcarbonyl-l-prolyl-trans-4-aminocyclohexylmethylamide (1), by replacing the aminocyclohexyl P1 group provided a new lead structure, 9-hydroxy-9-fluorenylcarbonyl-l-prolyl-2-aminomethyl-5-chlorobenzylamide (2), with improved potency (K(i) = 0.49 nM for human thrombin, 2x APTT = 0.37 microM in human plasma) and pharmacokinetic properties (F = 39%, iv T(1/2) = 13 h in dogs). An effective strategy for reducing plasma protein binding of 2 and improving efficacy in an in vivo thrombosis model in rats was to replace the lipophilic fluorenyl group in P3 with an azafluorenyl group. Systematic investigation of all possible azafluorenyl P3 isomers and azafluorenyl-N-oxide analogues of 2 led to the identification of an optimal compound, 3-aza-9-hydroxyfluoren-9(R)-ylcarbonyl-l-prolyl-2-aminomethyl-5-chlorobenzylamide (19b), with high potency (K(i) = 0.40 nM, 2x APTT = 0.18 microM), excellent pharmacokinetic properties (F = 55%, T(1/2) = 14 h in dogs), and complete efficacy in the in vivo thrombosis model in rats (inhibition of FeCl(3)-induced vessel occlusions in six of six rats receiving an intravenous infusion of 10 microg/kg/min of 19b). The stereochemistry of the azafluorenyl group in 19b was determined by X-ray crystallographic analysis of its N-oxide derivative (23b) bound in the active site of human thrombin.

  DOI：

  10.1021/jm049423s
• 作为产物：
  描述：

  4'-氯代新戊酰苯胺 在 硫酸 、 尿素 、 sodium nitrite 作用下， 反应 2.0h， 生成 7-chloro-5H-indeno[1,2-b]pyridin-5-one
  参考文献：
  名称：

  A general synthesis of substituted fluorenones and azafluorenones

  摘要：

  DOI：

  10.1021/jo00250a019

文献信息

• Thrombin inhibitors
  申请人：——

  公开号：US20020119992A1

  公开（公告）日：2002-08-29

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: 1 or a pharmaceutically acceptable salt thereof, e.g. where R 3 is —CH 2 NH 2 , —CH 2 CH 2 NH 2 , or —CH 2 NHC(O)OC(CH 3 ) 3 .

  该发明的化合物在抑制凝血酶和相关血栓闭塞方面具有以下结构： 1 或其药用可接受的盐，例如其中R 3 为—CH 2 NH 2 ，—CH 2 CH 2 NH 2 ，或—CH 2 NHC(O)OC(CH 3 ) 3 。
• Scope of Successive C–H Functionalizations of the Methyl Group in 3-Picolines: Intramolecular Carbonylation of Arenes to the Metal-Free Synthesis of 4-Azafluorenones
  作者：Joydev K. Laha、Krupal P. Jethava、Sagarkumar Patel

  DOI：10.1021/acs.orglett.5b03071

  日期：2015.12.4

  in 2-aryl-3-picolines via oxidative C–H functionalizations of the methyl group has been developed, providing an expedient synthesis of 4-azafluorenones. Distinct from the current literature wherein methylarenes have been used as acylating agents, 2-aryl-3-picolines in this study are transformed into aldehydes, which give 4-azafluorenones upon rapid intramolecular acylation. The study demonstrates the

  已经开发了一种无过渡金属的t - BuOOH介导的2-芳基-3-甲基吡啶中的芳烃分子内羰基化，该甲基化是通过甲基的CH-H官能化来实现的，可方便地合成4-氮杂芴酮。与现有文献不同，其中甲基芳烃已被用作酰化剂，本研究中的2-芳基-3-甲基吡啶被转化为醛，在快速分子内酰化后可生成4-氮杂芴酮。该研究证明了利用甲基作为潜在的羰基官能度的芳烃分子内羰基化的第一个例子。
• Synthesis of Azafluorenones using Zeolites.
  作者：R. Sreekumar、P. Rugmini、R. Padmakumar

  DOI：10.1080/00397919808007183

  日期：1998.6

  Abstract A convenient method for the synthesis of various azafluorenones (2a-f & 4a-d) by cyclization of substituted arylpyridines (1a-f & 3a-d) using zeolites are described.

  摘要描述了使用沸石环化取代的芳基吡啶 (1a-f & 3a-d) 合成各种氮杂芴酮 (2a-f & 4a-d) 的简便方法。
• [EN] COMPOUNDS COMPRISING A HETERO-FLUORENE GROUP<br/>[FR] COMPOSÉS COMPRENANT UN GROUPE HÉTÉRO-FLUORÈNE
  申请人：NOVALED GMBH

  公开号：WO2020221570A1

  公开（公告）日：2020-11-05

  The present invention relates to a compound, and to an organic semiconductor layer comprising this compound, suitable for use as an organic semiconductor layer for electronic devices, and a method of manufacturing the same, wherein the compound comprises a hetero-fluorene group and is represented by formula 1.

  本发明涉及一种化合物，以及包含该化合物的有机半导体层，适用于电子器件的有机半导体层，以及制造该化合物的方法，其中该化合物包含一个杂原芴基团，并由式1表示。
• HETERO-FLUORENE DERIVATIVES AND THEIR USE IN ELECTRONIC DEVICES
  申请人：Novaled GmbH

  公开号：EP3733649A1

  公开（公告）日：2020-11-04

  The present invention relates to a compound, and to an organic semiconductor layer comprising this compound, suitable for use as an organic semiconductor layer for electronic devices, and a method of manufacturing the same, wherein the compound comprises a hetero-fluorene group and is represented by formula 1:

  本发明涉及一种适合用作电子设备有机半导体层的化合物和包含该化合物的有机半导体层，以及制造该化合物的方法，其中该化合物包含一个杂芴基团，并由式 1 表示：