1-acetyl-6-methoxy-1,2-dihydro-3H-indol-3-one | 68095-10-3

• 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: 1-acetyl-6-methoxy-1,2-dihydro-3H-indol-3-one
• 英文别名: 1-acetyl-6-methoxy-2H-indol-3-one
• CAS: 68095-10-3
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: YWGWFIKPXXUWDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-6-methoxy-1,2-dihydro-3H-indol-3-one 在 三溴化硼 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (Z)-2-(2,4-dihydroxybenzylidene)-6-hydroxyindolin-3-one
  参考文献：
  名称：

  Resorcinol-based hemiindigoid derivatives as human tyrosinase inhibitors and melanogenesis suppressors in human melanoma cells

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114972
• 作为产物：
  描述：

  2-amino-4-methoxy-ω-chloroacetophenone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-acetyl-6-methoxy-1,2-dihydro-3H-indol-3-one
  参考文献：
  名称：

  [EN] 6,7,8,9-SUBSTITUTED 1-PHENYL-1,5-DIHYDRO-PYRIDO[3,2-B]INDOL-2-ONES USEFUL AS ANTI-INFECTIVE PHARMACEUTICAL AGENTS
  [FR] 6,7,8,9-SUBSTITUE 1-PHENYL-1,5-DIHYDRO-PYRIDO[3,2-B]INDOL-2-ONES CONVENANT COMME AGENTS PHARMACEUTIQUES ANTI-INFECTIEUX

  摘要：

  本发明涉及化合物(I)；其N-氧化物、盐、立体异构体、外消旋混合物、前药、酯和代谢物，其中X是NR2，O，S，SO，SO2；R1是氢、氰基、卤素、取代的羰基、甲亚胺基、N-羟基甲亚胺基、单或双(C1-4烷基)甲亚胺基、Het1或Het2；n是1、2或3；R2是氢、由自由基-COOR4取代的芳基；或R2是取代的C1-10烷基、C2-10烯基或C3-7环烷基；或R2是公式(b-1)；(b-2)；的自由基-CpH2p-CH(OR14)-CqH2q-R15 (b-3)；-CH2-CH2-(O-CH2-CH2)m-OR14 (b-4)；-CH2-CH2-(O-CH2-CH2)m-NR5aR5b (b-5)；-a1=a2-a3=a4-是-CH=CH-CH=CH-；-N=CH-CH=CH-；-CH=N-CH=CH-；-CH=CH-N=CH-；-CH=CH-CH=N-(c-5)；其中(c-1)-(c-5)中的一个氢原子被特定自由基取代；R3是硝基、氰基、氨基、卤素、羟基、C1-4烷氧基、羟基羰基、取代羰基、甲亚胺基、单或双(C1-4烷基)甲亚胺基、N-羟基甲亚胺基或Het1。

  公开号：

  WO2005111035A1

文献信息

• Indole acetic acid derivatives and their use as pharmaceutical agents
  申请人：Ma Xin

  公开号：US20060264486A1

  公开（公告）日：2006-11-23

  This invention is directed to indole acetic acid derivatives and their use in pharmaceutical compositions for the treatment of diseases such as diabetes, obesity, hyperlipidemia, and atherosclerotic disease. The invention is also directed to intermediates useful in preparation of indole acetic derivatives and to methods of preparation.

  这项发明涉及吲哚乙酸衍生物及其在制备药物组合物中的应用，用于治疗糖尿病、肥胖症、高脂血症和动脉粥样硬化等疾病。该发明还涉及在制备吲哚乙酸衍生物中有用的中间体和制备方法。
• 6,7,8,9-SUBSTITUTED 1-PHENYL-1,5-DIHYDRO-PYRIDO[3,2-B]INDOL-2-ONES USEFUL AS ANTI-INFECTIVE PHARMACEUTICAL AGENTS
  申请人：Kesteleyn Bart Rudolf Romanie

  公开号：US20100029635A1

  公开（公告）日：2010-02-04

  This invention concerns the compounds the N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein X is NR 2 , O, S, SO, SO 2 ; R 1 is hydrogen, cyano, halo, substituted carbonyl, methanimidamidyl, N-hydroxy-methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, Het 1 or Het 2 ; n is 1, 2 or 3; R 2 is hydrogen, aryl substituted with a radical —COOR 4 ; or R 2 is substituted C 1-10 alkyl, C 2-10 alkenyl or C 3-7 cycloalkyl; or R 2 is a radical of formula: —C p H 2p —CH(OR 14 )—C q H 2q —R 15 (b-3); —CH 2 —CH 2 —(O—CH 2 —CH 2 ) m —OR 14 (b-4); —CH 2 —CH 2 —(O—CH 2 —CH 2 ) m —NR 5a R 5b (b-5) -a 1 =a 2 -a 3 =a 4 - is —CH═CH—CH═CH—; —N═CH—CH═CH—; —CH═N—CH═CH—; —CH═CH—N═CH—; —CH═CH—CH═N— (c-5); wherein one of the hydrogen atoms in (c-1)-(c-5) is replaced by particular radicals; R 3 is nitro, cyano, amino, halo, hydroxy, C 1-4 alkyloxy, hydroxycarbonyl, substituted carbonyl, methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, N-hydroxy-methanimidamidyl or Het 1 .

  本发明涉及N-氧化物化合物、盐、立体异构体、外消旋混合物、前药、酯及其代谢物，其中X为NR2、O、S、SO、SO2；R1为氢、氰基、卤素、取代的羰基、甲基亚胺基、N-羟基甲基亚胺基、单或双(C1-4烷基)甲基亚胺基、Het1或Het2；n为1、2或3；R2为氢、芳基取代基，其取代基为—COOR4；或R2为取代的C1-10烷基、C2-10烯基或C3-7环烷基；或R2为式子：—CpH2p—CH(OR14)—CqH2q—R15(b-3)；—CH2—CH2—(O—CH2—CH2)m—OR14(b-4)；—CH2—CH2—(O—CH2—CH2)m—NR5aR5b(b-5)-a1=a2-a3=a4-为—CH═CH—CH═CH—；—N═CH—CH═CH—；—CH═N—CH═CH—；—CH═CH—N═CH—；—CH═CH—CH═N—(c-5)；其中(c-1)-(c-5)中的一个氢原子被特定的基团替换；R3为硝基、氰基、氨基、卤素、羟基、C1-4烷氧基、羟基羰基、取代的羰基、甲基亚胺基、单或双(C1-4烷基)甲基亚胺基、N-羟基甲基亚胺基或Het1。
• 6,7,8,9-Substituted 1-phenyl-1,5-dihydro-pyrido[3,2-b]indol-2-ones useful as anti-infective pharmaceutical agents
  申请人：Kesteleyn Rudolf Romanie Bart

  公开号：US20070167434A1

  公开（公告）日：2007-07-19

  This invention concerns the compounds the N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein X is NR 2 , O, S, SO, SO 2 ; R 1 is hydrogen, cyano, halo, substituted carbonyl, methanimidamidyl, N-hydroxy-methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, Het 1 or Het 2 ; n is 1, 2 or 3; R 2 is hydrogen, aryl substituted with a radical —COOR 4 ; or R 2 is substituted C 1-10 alkyl, C 2-20 alkenyl or C 3-7 cycloalkyl; or R is a radical of formula: —C p H 2p —CH(OR 14 )—C q H 2q —R 15 (b-3); —CH 2 —CH 2 —(O—CH 2 —CH 2 ) m —OR 14 (b-4); —CH 2 —CH 2 —(O—CH 2 —CH 2 ) m —NR 5a R 5b (b-5); -a 1 =a 2 -a 3 =a 4 - is —CH═CH—CH═CH—; —N═CH—CH═CH—; —CH═N—CH═CH—; —CH═CH—N═CH—; —CH═CH—CH═N— (c-5); wherein one of the hydrogen atoms in (c-1)-(c-5) is replaced by particular radicals; R 3 is nitro, cyano, amino, halo, hydroxy, C 1-4 alkyloxy, hydroxycarbonyl, substituted carbonyl, methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, N-hydroxy-methanimidamidyl or Het 1 .

  这项发明涉及化合物的N-氧化物、盐、立体异构体形式、外消旋混合物、前药、酯和代谢物，其中X是NR2、O、S、SO、SO2；R1是氢、氰、卤素、取代的羰基、甲基亚胺基、N-羟基甲基亚胺基、单或双(C1-4烷基)甲基亚胺基、Het1或Het2；n为1、2或3；R2为氢、芳基取代基，其中取代基为—COOR4；或R2为取代的C1-10烷基、C2-20烯基或C3-7环烷基；或R为以下公式的基团：—CpH2p—CH(OR14)—CqH2q—R15(b-3)；—CH2—CH2—(O—CH2—CH2)m—OR14(b-4)；—CH2—CH2—(O—CH2—CH2)m—NR5aR5b(b-5)；-a1=a2-a3=a4- 为—CH═CH—CH═CH—；—N═CH—CH═CH—；—CH═N—CH═CH—；—CH═CH—N═CH—；—CH═CH—CH═N—(c-5)；其中(c-1)-(c-5)中的一个氢原子被特定基团取代；R3为硝基、氰基、氨基、卤素、羟基、C1-4烷氧基、羟基羰基、取代羰基、甲基亚胺基、单或双(C1-4烷基)甲基亚胺基、N-羟基甲基亚胺基或Het1。
• Construction of C2‐Spirocyclopropyl‐Indolin‐3‐Ones through Base‐Promoted [2+1] Annulation Reaction of Indolin‐3‐ones with Bromosulfonium Salts
  作者：Mao Zhang、Fenfen Yang、Xiang Guan、Mingshan Shuai、Qingqing Zhang、Xiaozhong Fu、Yuanyong Yang、Meng Zhou、Bin He、Yonglong Zhao

  DOI：10.1002/ejoc.202300159

  日期：——

  base-promoted [2+1] annulation reaction has been developed for the synthesis of the structural diversity C2-spirocyclopropyl-indolin-3-ones. This [2+1] annulation process using simple and easily prepared nucleophilic indolin-3-ones (as C1 synthons) and bromosulfonium salts (as C2 synthons) as substrates, and realized the synthesis of C2-spirocyclopropyl-indolin-3-ones with up to 99 % yield and >20 : 1 dr.

  已经开发了一种简单有效的碱促进 [2+1] 环化反应，用于合成结构多样性 C2-spirocyclopropyl-indolin-3-ones。这种[2+1]环化过程以简单易制备的亲核三氢吲哚-3-酮(C1合成子)和溴硫盐(C2合成子)为底物，实现了C2-螺环丙基-3-二氢吲哚-酮的合成高达 99% 的产率和 >20 : 1 dr.
• Anodic C(sp³)–H Acyloxylation of Indolin-3-ones Enabled by Oxidant-Free Cross-Dehydrogenative C(sp³)–O Coupling
  作者：Canlin Zou、Hongting Wu、Jiangtao He、Yunfei Hu、Weijie Deng、Xinling Li、Jinhui Hu、Yibiao Li、Yubing Huang

  DOI：10.1021/acs.joc.1c02644

  日期：2022.1.21