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9H-Pyrrolo[2,1-b][1,3]benzoxazin-9-one

中文名称
——
中文别名
——
英文名称
9H-Pyrrolo[2,1-b][1,3]benzoxazin-9-one
英文别名
pyrrolo[2,1-b][1,3]benzoxazin-9-one
9H-Pyrrolo[2,1-b][1,3]benzoxazin-9-one化学式
CAS
——
化学式
C11H7NO2
mdl
——
分子量
185.182
InChiKey
QFDYOEYNMNPMSZ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.1
  • 重原子数:
    14
  • 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:
    31.2
  • 氢给体数:
    0
  • 氢受体数:
    2

反应信息

  • 作为产物:
    描述:
    (2-hydroxyphenyl)(1H-pyrrol-1-yl)methanone 在 palladium diacetate 、 lithium chloride 作用下, 以 四氢呋喃 为溶剂, 反应 14.0h, 以54%的产率得到9H-Pyrrolo[2,1-b][1,3]benzoxazin-9-one
    参考文献:
    名称:
    Synthesis of the novel antibacterial 6,8-dihydroxy-7-propyl-9H-pyrrolo[1,2-b][1,3]-benzoxazin-9-one
    摘要:
    The total synthesis of 6,8-dihydroxy-7-propyl-9H-pyrrolo[ 1,2-b][1,3]benzoxazin-9-one, a novel antibacterial agent, is described. The key step in the synthesis is achieved via an oxidative cyclization of a phenol to the 2-position of a pyrrole using stoichiometric Pd(OAc)(2). This provides a straightforward approach to the tricyclic structure of this prevously unreported template and future derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0040-4039(00)00590-6
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文献信息

  • Antibacterial agents
    申请人:Warner-Lambertt Company
    公开号:US06057315A1
    公开(公告)日:2000-05-02
    Described are antibacterial agents of formula (I): X is O, S or N--R.sub.8 ; R.sub.1, R.sub.2, R.sub.3 and R.sub.8 are independently H, straight or branched alkyl of 1-6 carbons, cycloalkyl of 3-6 carbons, alkenyl or alkynyl of from 2 to 6 atoms, R heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur, or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR.sub.2, NR'COR', CN, CO.sub.2 R' or CONR.sub.2 ', halogen, CN, CO.sub.2 R, COR, CON(R).sub.2, CON(R").sub.2, SR, SON, SCO.sub.2 R or SCON(R).sub.2 ; R.sub.4 is H, straight or branched alkyl of from 1-6 carbon atoms, alkenyl or alkynyl of from 2 to 6 atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR.sub.2, NR'COR', CN, CO.sub.2 R' or CONR.sub.2 ', halogen, CN, NO.sub.2, N(R).sub.2, NRCOR, NRCOR", COR, CO.sub.2 R, CON(R).sub.2, CON(R").sub.2, NRCON(R).sub.2, NRCO.sub.2 R; R.sub.5 is 1-6 straight or branched alkyl, a cycloalkyl of 3-6 carbons, alkenyl or alkynyl of from 2 to 6 atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR.sub.2, NR'COR', CN, CO.sub.2 R' or CONR.sub.2 ', halogen, OR, N(R).sub.2, NRCOR, NRCOR", COR, CON(R).sub.2, CON(R").sub.2, SR or SO.sub.2 R; R.sub.6, R.sub.7 are independently H, straight or branched alkyl of 1-6 carbons, cycloalkyl of 3-6 carbons, COR, COR", SO.sub.2 NR.sub.2, CONR.sub.2 and these may be optionally substituted by any of the groups listed for R.sub.5 ; R is H, straight or branched alkyl of 1-6 carbon atoms, cycloalkyl of from 3-6 carbon atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur, or pheny, all of which may be optionally substituted by halogen, OR', NR'.sub.2, NR'COR', CN, CO.sub.2 R', CONR'.sub.2, R' is H, alkyl of from 1-3 carbon atoms or Ph; R" is part of a naturally occurring amino acid connected via an amide or acyl bond as determined by the formula; halogen is any one of fluoro, chloro, bromo or iodo; or a pharmaceutically acceptable salt.
    本文描述了化学式(I)的抗菌剂:X为O,S或N-R.sub.8; R.sub.1,R.sub.2,R.sub.3和R.sub.8独立地为1-6个碳原子的直链或支链烷基,3-6个碳原子的环烷基,2-6个原子的烯基或炔基,5-8个原子的R杂环,其中1-3个杂原子为氮、氧或硫,或苯基,所有这些环可以选择性地被卤素、OR、NR.sub.2、NR'COR'、CN、CO.sub.2 R'或CONR.sub.2'、卤素、CN、CO.sub.2 R、COR、CON(R).sub.2、CON(R").sub.2、SR、SON、SCO.sub.2 R或SCON(R).sub.2取代最多3次;R.sub.4为1-6个碳原子的直链或支链烷基,2-6个原子的烯基或炔基,5-8个原子的R杂环,其中1-3个杂原子为氮、氧或硫或苯基,所有这些环可以选择性地被卤素、OR、NR.sub.2、NR'COR'、CN、CO.sub.2 R'或CONR.sub.2'、卤素、CN、NO.sub.2、N(R).sub.2、NRCOR、NRCOR"、COR、CO.sub.2 R、CON(R).sub.2、CON(R").sub.2、NRCON(R).sub.2、NRCO.sub.2 R取代最多3次;R.sub.5为1-6个直链或支链烷基,3-6个碳原子的环烷基,2-6个原子的烯基或炔基,5-8个原子的R杂环,其中1-3个杂原子为氮、氧或硫或苯基,所有这些环可以选择性地被卤素、OR、NR.sub.2、NR'COR'、CN、CO.sub.2 R'或CONR.sub.2'、卤素、OR、N(R).sub.2、NRCOR、NRCOR"、COR、CON(R).sub.2、CON(R").sub.2、SR或SO.sub.2 R取代最多3次;R.sub.6,R.sub.7独立地为1-6个碳原子的直链或支链烷基,3-6个碳原子的环烷基,COR,COR",SO.sub.2 NR.sub.2,CONR.sub.2,这些可以选择性地被列在R.sub.5中的任何一组取代;R为1-6个碳原子的直链或支链烷基,从3-6个碳原子的环烷基,5-8个原子的R杂环,其中1-3个杂原子为氮、氧或硫,或苯基,所有这些可以选择性地被卤素、OR'、NR'.sub.2、NR'COR'、CN、CO.sub.2 R'、CONR'.sub.2取代,其中R'为1-3个碳原子的烷基或苯基;R"是通过酰胺或酰基键连接的天然氨基酸的一部分,由公式确定;卤素是氟、氯、溴或碘中的任何一种;或药学上可接受的盐。
  • ANTIBACTERIAL AGENTS
    申请人:WARNER-LAMBERT COMPANY
    公开号:EP0942912A1
    公开(公告)日:1999-09-22
  • US6057315A
    申请人:——
    公开号:US6057315A
    公开(公告)日:2000-05-02
  • [EN] ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTERIENS
    申请人:WARNER-LAMBERT COMPANY
    公开号:WO1998025932A1
    公开(公告)日:1998-06-18
    (EN) Described are antibacterial agents of formula (I): X is O, S or N-R8; R1, R2, R3 and R8 are independently H, straight or branched alkyl of 1-6 carbons, cycloalkyl of 3-6 carbons, alkenyl or alkynyl of from 2 to 6 atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur, or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR2, NR'COR', CN, CO2R' or CONR2', halogen, CN, CO2R, COR, CON(R)2, CON(R')2, SR, SON, SCO2R or SCON(R)2; R4 is H, straight or branched alkyl of from 1-6 carbon atoms, alkenyl or alkynyl of from 2 to 6 atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR2, NR'COR', CN, CO2R' or CONR2', halogen, CN, NO2, N(R)2, NRCOR, NRCOR', COR, CO2R, CON(R)2, CON(R')2, NRCON(R)2, NRCO2R; R5 is 1-6 straight or branched alkyl, a cycloalkyl of 3-6 carbons, alkenyl or alkynyl of from 2 to 6 atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR2, NR'COR', CN, CO2R' or CONR2', halogen, OR, N(R)2, NRCOR, NRCOR', COR, CON(R)2, CON(R')2, SR or SO2R; R6, R7 are independently H, straight or branched alkyl of 1-6 carbons, cycloalkyl of 3-6 carbons, COR, COR', SO2NR2, CONR2 and these may be optionally substituted by any of the groups listed for R5; R is H, straight or branched alkyl of 1-6 carbon atoms, cycloalkyl of from 3-6 carbon atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur, or pheny, all of which may be optionally substituted by halogen, OR', NR'2, NR'COR', CN, CO2R', CONR'2; R' is H, alkyl of from 1-3 carbon atoms or Ph; R' is part of a naturally occurring amino acid connected via an amide or acyl bond as determined by the formula; halogen is any one of fluoro, chloro, bromo or iodo; or a pharmaceutically acceptable salt.(FR) L'invention porte sur des agents antibactériens de la formule (I) dans laquelle X est O, S ou N-R8; R1, R2, R3 et R8 sont indépendamment H, alkyle droit ou ramifié de 1 à 6 carbones, cycloalkyle de 3 à 6 carbones, alcényle ou alkynyle de 2 à 6 atomes, un noyau hétérocyclique de 5 à 8 atomes dans lesquels 1 à 3 hétéroatomes sont azote, oxygène ou soufre ou phényle, lesdits noyaux pouvant tous être éventuellement substitués jusqu'à trois fois par halogène, OR, NR2, NR'COR', CN, CO2R' ou CONR2', halogène, CN, CO2R, COR, CON(R)2, CON(R')2, SR, SON, SCO2R ou SCON(R)2; R4 est H, alkyle droit ou ramifié de 1 à 6 carbones, alcényle ou alkynyle de 2 à 6 atomes, un noyau hétérocyclique de 5 à 8 atomes dans lesquels 1 à 3 hétéroatomes sont azote, oxygène ou soufre ou phényle, lesdits noyaux pouvant tous être éventuellement substitués jusqu'à trois fois par halogène, OR, NR2, NR'COR', CN, CO2R' ou CONR2', halogène, CN, NO2, N(R)2, NRCOR, NRCOR', COR, CO2R, CON(R)2, CON(R')2, NRCON(R)2; NRCO2R; R5 est alkyle droit ou ramifié de 1 à 6 carbones, cycloalkyle de 3 à 6 carbones, alcényle ou alkynyle de 2 à 6 atomes, un noyau hétérocyclique de 5 à 8 atomes dans lesquels 1 à 3 hétéroatomes sont azote, oxygène ou soufre ou phényle, lesdits noyaux pouvant tous être éventuellement substitués jusqu'à trois fois par halogène, OR, NR2, NR'COR', CN, CO2R' ou CONR2', halogène, OR, N(R)2, NRCOR, NRCOR', COR, CON(R)2, CON(R')2, SR ou SO2,R; R6 et R7 sont indépendamment H, alkyle droit ou ramifié de 1 à 6 carbones, cycloalkyle de 3 à 6 carbones, COR, COR', SO2NR2, CONR2, lesdits groupes pouvant être éventuellement substitués par l'un quelconque des groupes énumérés sous R5; R est H, alkyle droit ou ramifié de 1 à 6 atomes de carbone, cycloalkyle de 3 à 6 carbones, un noyau hétérocyclique de 5 à 8 atomes dans lesquels 1 à 3 hétéroatomes sont azote, oxygène ou soufre ou phényle, lesdits noyaux pouvant tous être éventuellement substitués par halogène, OR', NR'2, NR'COR', CN, CO2R' ou CONR'2; R' est H, alkyle de 1 à 3 atomes de carbone ou Ph; R' est partie intégrante d'un acide aminé naturel relié par l'intermédiaire d'une liaison amide ou acyle telle que déterminée par ladite formule; halogène est un quelconque des sels fluoro, chloro, bromo ou iodo, ou un sel pharmaceutiquement acceptable.
  • Synthesis of the novel antibacterial 6,8-dihydroxy-7-propyl-9H-pyrrolo[1,2-b][1,3]-benzoxazin-9-one
    作者:Liren Huang、Edmund L Ellsworth、Sab Randhawa、Michael A Stier、Yanting Huang、Paul Bird、Mikhail Lebedev、Kun Wu、Ron G Micetich、John M Domagala、Rajeshwar Singh、Norm L Colbry
    DOI:10.1016/s0040-4039(00)00590-6
    日期:2000.5
    The total synthesis of 6,8-dihydroxy-7-propyl-9H-pyrrolo[ 1,2-b][1,3]benzoxazin-9-one, a novel antibacterial agent, is described. The key step in the synthesis is achieved via an oxidative cyclization of a phenol to the 2-position of a pyrrole using stoichiometric Pd(OAc)(2). This provides a straightforward approach to the tricyclic structure of this prevously unreported template and future derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.
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同类化合物

2,9-二(2-苯乙基)蒽并[2,1,9-DEF:6,5,10-D’E’F’]二异喹啉-1,3,8,10(2H,9H)-四酮 (βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-(+)-5,5'',6,6'',7,7'',8,8''-八氢-3,3''-二叔丁基-1,1''-二-2-萘酚,双钾盐 (S)-盐酸沙丁胺醇 (S)-7,7-双[(4S)-(苯基)恶唑-2-基)]-2,2,3,3-四氢-1,1-螺双茚满 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2-N-Fmoc-氨基甲基吡咯烷盐酸盐 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-7,7-双[(4S)-(苯基)恶唑-2-基)]-2,2,3,3-四氢-1,1-螺双茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-3,3''-双([[1,1''-联苯]-4-基)-[1,1''-联萘]-2,2''-二醇 (R)-2-[((二苯基膦基)甲基]吡咯烷 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4S,5R)-3,3a,8,8a-四氢茚并[1,2-d]-1,2,3-氧杂噻唑-2,2-二氧化物-3-羧酸叔丁酯 (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aS,8aR)-2-(吡啶-2-基)-8,8a-二氢-3aH-茚并[1,2-d]恶唑 (3aS,3''aS,8aR,8''aR)-2,2''-环戊二烯双[3a,8a-二氢-8H-茚并[1,2-d]恶唑] (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (3S,3aR)-2-(3-氯-4-氰基苯基)-3-环戊基-3,3a,4,5-四氢-2H-苯并[g]吲唑-7-羧酸 (3R,3’’R,4S,4’’S,11bS,11’’bS)-(+)-4,4’’-二叔丁基-4,4’’,5,5’’-四氢-3,3’’-联-3H-二萘酚[2,1-c:1’’,2’’-e]膦(S)-BINAPINE (3-三苯基甲氨基甲基)吡啶 (3-[(E)-1-氰基-2-乙氧基-2-hydroxyethenyl]-1-氧代-1H-茚-2-甲酰胺) (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,4S)-Fmoc-4-三氟甲基吡咯烷-2-羧酸 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,3R)-3-(叔丁基)-2-(二叔丁基膦基)-4-甲氧基-2,3-二氢苯并[d][1,3]氧杂磷杂戊环 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-二甲氧基-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S,2''S,3S,3''S)-3,3''-二叔丁基-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2R,2''R,3R,3''R)-3,3''-二叔丁基-4,4''-二甲氧基-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2-硝基苯基)磷酸三酰胺 (2-氯-6-羟基苯基)硼酸 (2-氟-3-异丙氧基苯基)三氟硼酸钾 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1α,1'R,4β)-4-甲氧基-5''-甲基-6'-[5-(1-丙炔基-1)-3-吡啶基]双螺[环己烷-1,2'-[2H]indene (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1R,1′R,2S,2′S)-2,2′-二叔丁基-2,3,2′,3′-四氢-1H,1′H-(1,1′)二异磷哚