2-(2-溴-5-甲氧基苯基)乙酰胺 | 27387-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-溴-5-甲氧基苯基)乙酰胺
• 英文名称: 2-bromo-5-methoxyphenylacetamide
• 英文别名: 2-(2-bromo-5-methoxyphenyl)acetamide
• CAS: 27387-22-0
• 化学式: C₉H₁₀BrNO₂
• 分子量: 244.088
• InChiKey: PFYYKHQLFPPBPC-UHFFFAOYSA-N

物化性质

• 沸点：
  408.5±35.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-溴-5-甲氧基苯基)乙酰胺 在 copper(I) oxide 、 邻苯二胺 、 sodium t-butanolate 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以70%的产率得到5-甲氧基吲哚酮
  参考文献：
  名称：

  Efficient copper-catalyzed intramolecular N-arylation for the synthesis of oxindoles

  摘要：

  An efficient copper-catalyzed intramolecular N-arylation was performed by using substituted 2-(2-bromoaryl)acetamide with small amount of Cu2O and benzene-1,2-diamine as catalytic system under aerobic conditions, which provided good to excellent yields of oxindoles with tolerance of a wide variety of substrates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.082
• 作为产物：
  描述：

  2-(2-溴-5-甲氧基苯基)乙腈 在 sodium hydroxide 、 叔丁醇 作用下， 生成 2-(2-溴-5-甲氧基苯基)乙酰胺
  参考文献：
  名称：

  Efficient copper-catalyzed intramolecular N-arylation for the synthesis of oxindoles

  摘要：

  An efficient copper-catalyzed intramolecular N-arylation was performed by using substituted 2-(2-bromoaryl)acetamide with small amount of Cu2O and benzene-1,2-diamine as catalytic system under aerobic conditions, which provided good to excellent yields of oxindoles with tolerance of a wide variety of substrates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.082

文献信息

• The palladium(<scp>ii</scp>)-catalyzed regioselective <i>ortho</i>-C–H bromination/iodination of arylacetamides with <i>in situ</i> generated imidic acid as the directing group: mechanistic exploration
  作者：Yogesh Jaiswal、Yogesh Kumar、Amit Kumar

  DOI：10.1039/c9ob01082c

  日期：——

  study, we report the palladium(ii)-catalyzed regioselective ortho-C-H bromination/iodination of challenging arylacetamide derivatives using N-halosuccinimides as halogenating agents. Diverse arylacetamides underwent the regioselective ortho-bromination and iodination of aromatic C-H bonds in the presence of a reactive benzylic C(sp3)-H bond without installing any bulky auxiliaries via unfavorable six-membered

  在本研究中，我们报道了使用N-卤代琥珀酰亚胺作为卤化剂，钯（ii）催化的具有挑战性的芳基乙酰胺衍生物的区域选择性邻CH溴化/碘化。在不存在不利的六元金属环的情况下，在没有反应性苄基C（sp3）-H键的情况下，对不同的芳基乙酰胺进行芳香族CH键的区域选择性邻溴化和碘化反应。弱的配位，使用普遍存在的伯酰胺挑战CH功能，简单的催化系统和广泛的底物范围是这种转化的关键特征。此外，卤代酰胺衍生物被转化成各种有价值的合成子。详细的机理研究揭示了有关反应途径的一些有趣方面。
• Dihydroisoquinoline derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0183369A2

  公开（公告）日：1986-06-04

  Compounds of the general formula I in which: R, and R2 are independently hydrogen, C, 6 alkyl ortogether are a group X which is C3 6 polymethylene optionally in which one carbon atom is replaced by O, S or NR6 wherein R6 is hydrogen or C1 6 alkyl; R3 is a mono- or fused bi-cyclic heteroaromatic group having up to ten atoms in the aromatic ring(s), not more than four of which are selected from nitrogen, oxygen or sulphur, optionally C-substituted by one or more substituents selected from halogen, CF3, nitro, C1-6 alkoxy, C1-6 alkylthio, C2-7 alkanoyl or cyano; or is phenyl or naphthyl, optionally substituted by one or more substituents selected from halogen, CF3, nitro, C1-6 alkyl, C1 6 alkoxy, C1 6 alkylthio, C2-7 alkanoyl, carboxyl, C1-6 alkoxycarbonyl, cyano, CONR7R8 wherein R7 and R8 are selected from hydrogen or C1-6 alkyl or together are a group X; NR9 R10 wherein R9 and R10 are selected from hydrogen, C1-6 alkyl, C2-7 alkanoyl or C1-6 alkylsulphonyl or together are a group X; SO2NR11R12 wherein R11 and R12 are selected from hydrogen or C1-6 alkyl or together are a group X; or S(O)mR13 wherein m is 1 or 2 and R13 is C1-6 alkyl; Z is naphthyl or a mono- or fused bycyclic heteroaromatic ring having up to ten atoms in the aromatic ring(s), not more than four of which are selected from nitrogen, oxygen or sulphur or (when R3 is an optionally substituted naphthyl or heteroaromatic group as defined) Z is a phyenyl ring; and Z is optionally C-substituted by one or two substituents R4 and R5 which are independently selected from C1-6 alkyl, cyano, amino, aminocarbonyl or aminocarbamoyl optionally substituted by one or two C1-6 alkyl groups or by a group X, halogen, CF3, nitro, C1-6 alkoxy, C1-6 alkylthio, C2-7 alkanoyloxy or hydroxy, or together on adjacent carbon atoms are methylenedioxy or C3-5 polymethylene, are disclosed as an active therapeutic substances for the treatment of inflammatory conditions.

  通式 I 的化合物 其中 R 和 R2 独立地为氢、C, 6 烷基或共同为基团 X，该基团为 C3 6 聚亚甲基，其中一个碳原子可选地被 O、S 或 NR6 取代，其中 R6 为氢或 C1 6 烷基； R3 是单环或融合双环杂芳香族基团，在芳香环中最多有 10 个原子，其中不超过 4 个原子选自氮、氧或硫，可选择被一个或多个选自卤素、CF3、硝基、C1-6 烷氧基、C1-6 烷硫基、C2-7 烷酰基或氰基的取代基取代；或苯基或萘基，任选被一个或多个选自卤素、 、硝基、C1-6 烷基、C1-6 烷氧基、C1-6 烷硫基、C2-7 烷酰基、羧基、C1-6 烷氧羰基、氰基的取代基取代； CONR7R8 其中 R7 和 R8 选自氢或 C1-6 烷基，或共同组成基团 X；NR9 R10，其中 R9 和 R10 选自氢、C1-6 烷基、C2-7 烷酰基或 C1-6 烷基磺酰基，或两者同为一个基团 X； SO2NR11R12，其中 R11 和 R12 选自氢或 C1-6 烷基，或两者同为一个基团 X；或 S(O)mR13 其中 m 为 1 或 2，R13 为 C1-6 烷基； Z 为萘基或单环或融合环状杂芳香族环，其芳香环中最多有 10 个原子，其中不超过 4 个原子选自氮、氧或硫，或（当 R3 为任选取代的萘基或定义的杂芳香族基团时）Z 为茚基环；Z任选被一个或两个取代基 R4 和 R5 取代，这两个取代基独立地选自 C1-6 烷基、氰基、氨基、氨基羰基或氨基甲酰基，任选被一个或两个 C1-6 烷基或基团 X、卤素、 、硝基、C1-6 烷氧基、C1-6 烷硫基、C2-7 烷酰氧基或羟基取代，或在相邻碳原子上一起被亚甲基二氧基或 C3-5 聚亚甲基取代。
• Synthesis of Aryl- and Heteroaryl[<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazoles
  作者：Concha Sanchez-Martinez、Margaret M. Faul、Chuan Shih、Kevin A. Sullivan、John L. Grutsch、Jeremy T. Cooper、Stanley P. Kolis

  DOI：10.1021/jo034207x

  日期：2003.10.1

  Synthesis of aryl- and hetero[a]pyrrolo[3,4-c]carbazoles by photochemical oxidation and Heck cyclization are described. Photochemical oxidation of 2-naphthyl indolyl maleimide affords two different carbazole regioisomers, depending on the reaction conditions. The regiochemistry of the cyclization can be controlled using the Heck reaction.
• US4745115A
  申请人：——

  公开号：US4745115A

  公开（公告）日：1988-05-17