6-硝基-2-苯基-4-喹啉醇 | 56983-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 6-硝基-2-苯基-4-喹啉醇
• 英文名称: 2-Phenyl-6-nitro-4-hydroxy-chinolin
• 英文别名: 4-Hydroxy-6-nitro-2-phenylquinoline；6-Nitro-2-phenylquinolin-4-ol；6-nitro-2-phenyl-1H-quinolin-4-one
• CAS: 56983-10-9
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: KFCTXLVNHOGMHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-硝基-2-苯基-4-喹啉醇 、 三氯氧磷 、 五氯化磷 生成 4-chloro-6-nitro-2-phenylquinoline
  参考文献：
  名称：

  DESAI K.; DESAI C. M., J. INDIAN CHEM. SOC. , 1975, 52, NO 5, 448-449

  摘要：

  DOI：
• 作为产物：
  描述：

  在 二乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以208 mg的产率得到6-硝基-2-苯基-4-喹啉醇
  参考文献：
  名称：

  Synthesis of 4-Quinolones via a Carbonylative Sonogashira Cross-Coupling Using Molybdenum Hexacarbonyl as a CO Source

  摘要：

  A palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence for the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes via two different protocols is described. The first method (A) yields the cyclized products after only 20 min of microwave (MW) heating at 120 degrees C. The second method (B) is a gas-free one-pot two-step sequence which runs at room temperature, allowing the use of sensitive substituents (e.g., nitro and bromide groups). For both protocols, molybdenum hexacarbonyl was used as a solid source of CO.

  DOI：

  10.1021/jo502400h

文献信息

• One-Pot Allan-Robinson/Friedländer Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes
  作者：Vijai K. Rai、Fooleswar Verma、Ganeshwar P. Sahu、Manorama Singh、Ankita Rai

  DOI：10.1002/ejoc.201701435

  日期：2018.1.31

  A domino reaction between 2‐hydroxy‐/2‐aminobenzaldehydes and α‐haloketones gives chromen‐4‐ones and quinolin‐4‐ones in good to excellent yields. This method represents a new extension of the Allan–Robinson and Friedländer reactions, and uses N‐heterocyclic‐carbene catalysis. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by‐product formation.

  2-羟基/ 2-氨基苯甲醛与α-卤代酮之间的多米诺反应使chromen-4-ones和quinolin-4-ones的产率高到极好。该方法代表了Allan-Robinson和Friedländer反应的新扩展，并使用了N-杂环-卡宾催化。这种方法的优点是操作简单，环境反应条件好，并且不会形成副产物。
• [EN] HEPATITIS C INHIBITOR TRI-PEPTIDES<br/>[FR] TRI-PEPTIDES INHIBITEURS DE L'HEPATITE C
  申请人：BOEHRINGER INGELHEIM CA LTD

  公开号：WO2000009543A2

  公开（公告）日：2000-02-24

  Racemates, diastereoisomers and optical isomers of a compound of formula (I) wherein B is H, a C6 or C10 aryl, C7-16 aralkyl; Het or (lower alkyl)-Het, all of which optionally substituted with C1-6 alkyl; C1-6 alkoxy; C1-6 alkanoyl; hydroxy; hydroxyalkyl; halo; haloalkyl; nitro; cyano; cyanoalkyl; amino optionally substituted with C1-6 alkyl; amido; or (lower alkyl)amide; or B is an acyl derivative of formula R4-C(O)-; a carboxyl of formula R4-O-C(O)-; an amide of formula R4-N(R5)-C(O)-; a thioamide of formula R4-N(R5)-C(S)-;or a sulfonyl of formula R4-SO2; R5 is H or C1-6 alkyl; and Y is H or C1-6 alkyl; R3 is C¿1-8? alkyl, C3-7 cycloalkyl, or C4-10 alkylcycloalkyl, all optionally substituted with hydroxy, C1-6 alkoxy, C1-6 thioalkyl, amido, (lower alkyl)amido, C6 or C10 aryl, or C7-16 aralkyl; R2 is CH2-R20, NH-R20, O-R20or S-R20, wherein R20 is a saturated or unsaturated C3-7 cycloalkyl or C4-10 (alkylcycloalkyl), all of which being optionally mono-, di- or tri-substituted with R21, or R20 is a C6 or C10 aryl or C7-14 aralkyl optionally substituted, or R20 is Het or (lower alkyl)-Het, both optionally substituted, Het or (lower alkyl)-Het; carboxyl; carboxy(lower alkyl); C6 or C10 aryl, C7-14 aralkyl or Het, said aryl, aralkyl or Het being optionally substituted; and R?1¿ is H; C¿1-6? alkyl, C3-7 cycloalkyl, C2-6 alkenyl, or C2-6 alkynyl, all optionally substituted with halogen; or a pharmaceutically acceptable salt or ester thereof.

  化合物式（I）的同分异构体、对映异构体和光学异构体，其中B为H、C6或C10芳基、C7-16芳基烷基；Het或（较低烷基）-Het，所有这些都可以用C1-6烷基、C1-6烷氧基、C1-6烷酰基、羟基、羟基烷基、卤素、卤素烷基、硝基、氰基、氰基烷基、氨基（可选用C1-6烷基取代）、酰胺或（较低烷基）酰胺、或B是公式R4-C（O）-的酰衍生物；公式R4-O-C（O）-的羧基；公式R4-N（R5）-C（O）-的酰胺；公式R4-N（R5）-C（S）-的硫酰胺；或公式R4-SO2的磺酰基；R5为H或C1-6烷基；Y为H或C1-6烷基；R3为C1-8烷基、C3-7环烷基或C4-10烷基环烷基，所有这些都可以用羟基、C1-6烷氧基、C1-6硫代烷基、酰胺、（较低烷基）酰胺、C6或C10芳基或C7-16芳基烷基取代；R2为CH2-R20、NH-R20、O-R20或S-R20，其中R20为饱和或不饱和的C3-7环烷基或C4-10（烷基环烷基），所有这些都可以选择性地单、双或三取代R21，或者R20是C6或C10芳基或C7-14芳基烷基，可以选择性地取代，或者R20是Het或（较低烷基）-Het，两者都可以选择性地取代，Het或（较低烷基）-Het；羧基；羧基（较低烷基）；C6或C10芳基、C7-14芳基烷基或Het，所述芳基、芳基烷基或Het均可选择性地取代；以及R1为H；C1-6烷基、C3-7环烷基、C2-6烯基或C2-6炔基，所有这些都可以选择性地取代卤素；或其药学上可接受的盐或酯。
• Hepatitis C inhibitor tri-peptides
  申请人：——

  公开号：US20020037998A1

  公开（公告）日：2002-03-28

  Racemates, diastereoisomers and optical isomers of a compound of formula (I): 1 wherein B is H, a C 6 or C 10 aryl, C 7-16 aralkyl; Het or (lower alkyl)-Het, all of which optionally substituted with C 1-6 alkyl; C 1-6 alkoxy; C 1-6 alkanoyl; hydroxy; hydroxyalkyl; halo; haloalkyl; nitro; cyano; cyanoalkyl; amino optionally substituted with C 1-6 alkyl; amido; or (lower alkyl)amide; or B is an acyl derivative of formula R 4 —C(O)—; a carboxyl of formula R 4 —O—C(O)—; an amide of formula R 4 -N(R 5 )—C(O)—; a thioamide of formula R 4 —N(R 5 )—C(S)—;or a sulfonyl of formula R 4 —SO 2 ; R 5 is H or C 1-6 alkyl; and Y is H or C 1-6 alkyl; R 3 is C 1-8 alkyl, C 3-7 cycloalkyl, or C 4-10 alkylcycloalkyl, all optionally substituted with hydroxy, C 1-6 alkoxy, C 1-6 thioalkyl, amido, (lower alkyl)amido, C 6 or C 10 aryl, or C 7-16 aralkyl; R 2 is CH 2 -R 20 , NH—R 20 , O—R 20 or S—R 20 , wherein R 20 is a saturated or unsaturated C 3-7 cycloalkyl or C 4-10 (alkylcycloalkyl), all of which being optionally mono-, di- or tri- substituted with R 21 , or R 20 is a C 6 or C 10 aryl or C 7-14 aralkyl optionally substituted, or R 20 is Het or (lower alkyl)-Het, both optionally substituted, Het or (lower alkyl)-Het; carboxyl; carboxy(lower alkyl); C 6 or C 10 aryl, C 7-14 aralkyl or Het, said aryl, aralkyl or Het being optionally substituted; and R 1 is H; C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, or C 2-6 alkynyl, all optionally substituted with halogen; or a pharmaceutically acceptable salt or ester thereof.

  化合物公式（I）的竞争异构体，对映异构体和光学异构体：其中B为H、C6或C10芳基、C7-16芳基烷基、Het或（较低烷基）-Het，它们都可以选择性地用C1-6烷基、C1-6烷氧基、C1-6烷酰基、羟基、羟基烷基、卤素、卤素烷基、硝基、氰基、选择性地用C1-6烷基取代的氨基、酰胺或（较低烷基）酰胺；或B为公式R4-C（O）的酰衍生物；公式R4-O-C（O）的羧基；公式R4-N（R5）-C（O）的酰胺；公式R4-N（R5）-C（S）的硫酰胺；或公式R4-SO2的磺酰基；其中R5为H或C1-6烷基；Y为H或C1-6烷基；R3为C1-8烷基、C3-7环烷基或C4-10烷基环烷基，它们都可以选择性地用羟基、C1-6烷氧基、C1-6硫代烷基、酰胺、（较低烷基）酰胺、C6或C10芳基或C7-16芳基烷基取代；R2为CH2-R20、NH-R20、O-R20或S-R20，其中R20为饱和或不饱和的C3-7环烷基或C4-10（烷基环烷基），它们都可以选择性地用R21单取代、双取代或三取代，或R20为C6或C10芳基或C7-14芳基烷基，可以选择性地取代，或R20为Het或（较低烷基）-Het，两者都可以选择性地取代，Het或（较低烷基）-Het；羧基；羧基（较低烷基）；C6或C10芳基、C7-14芳基烷基或Het，所述芳基、芳基烷基或Het可以选择性地取代；以及R1为H、C1-6烷基、C3-7环烷基、C2-6烯基或C2-6炔基，它们都可以选择性地用卤素取代；或其药学上可接受的盐或酯。
• Quinoline derivatives as immunostimulants
  申请人：Pfizer Inc.

  公开号：US05506235A1

  公开（公告）日：1996-04-09

  This invention relates to compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined hereinbelow that exhibit activity as immunostimulants.

  本发明涉及公式 ##STR1## 中R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，R.sup.6和R.sup.7的化合物，这些化合物表现出免疫刺激活性。
• Pharmacologically active amides, processes for their preparation and
  申请人：Rhone-Poulenc Sante

  公开号：US04788199A1

  公开（公告）日：1988-11-29

  Amides of formula: ##STR1## in which A is ##STR2## V and W are H, halogen, alkyl (1-3C), alkoxy (1-3C), NO.sub.2 or CF.sub.3, Z is bound in the ortho or para position with respect to B and is phenyl, optionally substituted, thienyl or pyridyl, the chain X--(CH.sub.2).sub.n --(CHR).sub.m --CO--NR.sub.1 R.sub.2 is bound in the ortho or para position with respect to B, R is H or alkyl (1-3C), R.sub.1 and R.sub.2 are alkyl (1-6C), cycloalkyl (3-6C), phenyl, phenylalkyl, cycloalkylalkyl, alkenyl (3-6C), R.sub.1 and R.sub.2 can also form, with the nitrogen atom to which they are attached, a pyrrolidine, piperidine, morpholine or thiomorpholine ring, X is >CH--R.sub.3, >N--R.sub.4, >SO, >SO.sub.2, >O or >S, R.sub.3 is H, alkyl (1-3C), R.sub.4 is alkyl (1-3C) m=0 or 1 and n=0, 1 or 2, provided that, if X is >SO, >SO.sub.2 or >N--R.sub.4 , the sum m+n is equal to at least 1, that, when A and B are N and Z is in the para position with respect to B, X cannot denote the group >CH--R.sub.3 and that when A is CH, B is N, Z is in the ortho position with respect to B, X is an oxygen atom, and R is a hydrogen atom, the sum m+n is other than 1, and excluding 2-phenyl-4-quinolyl N,N-dimethylcarbamate, have useful pharmacological activity, e.g. as anxiolytics, anticonvulsants and antiangina agents.

  公式为：##STR1## 中，A为##STR2##，V和W为H，卤素，烷基（1-3C），烷氧基（1-3C），NO.sub.2或CF.sub.3，Z与B的正交或相对位置相连，为苯基，可选择性取代，噻吩基或吡啶基，链X--（CH.sub.2）.sub.n--（CHR）.sub.m--CO--NR.sub.1 R.sub.2与B的正交或相对位置相连，R为H或烷基（1-3C），R.sub.1和R.sub.2为烷基（1-6C），环烷基（3-6C），苯基，苯基烷基，环烷基烷基，烯基（3-6C），R.sub.1和R.sub.2还可以与它们附着的氮原子形成吡咯烷，哌嗪，吗啉或硫代吗啉环，X为>CH--R.sub.3，>N--R.sub.4，>SO，>SO.sub.2，>O或>S，R.sub.3为H，烷基（1-3C），R.sub.4为烷基（1-3C），m=0或1，n=0，1或2，前提是，如果X为>SO，>SO.sub.2或>N--R.sub.4，则m+n之和至少为1，当A和B为N且Z与B的相对位置为para时，X不能表示为>CH--R.sub.3，当A为CH，B为N，Z与B的相对位置为ortho时，X为氧原子，R为氢原子，m+n之和不为1，并且不包括2-苯基-4-喹啉基N，N-二甲基氨基甲酸酯，具有有用的药理活性，例如作为抗焦虑药，抗癫痫药和抗心绞痛药。