2-(2-iodophenyl)-N-phenylacetamide | 540803-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-iodophenyl)-N-phenylacetamide
• CAS: 540803-89-2
• 化学式: C₁₄H₁₂INO
• 分子量: 337.16
• InChiKey: OSFUFMGIPIECCH-UHFFFAOYSA-N

物化性质

• 熔点：
  165-167 °C(Solv: ethanol (64-17-5))
• 沸点：
  490.1±28.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-iodophenyl)-N-phenylacetamide 在 氢氧化钾 、 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4-butyl-3-phenyl-1H-3-benzazepin-2-one
  参考文献：
  名称：

  A regioselective synthesis of 3-benzazepinones via intramolecular hydroamidation of acetylenes

  摘要：

  Synthesis of 3-benzazepinones by palladium-catalyzed intramolecular addition of amides to alkynes is achieved. Phenyl acetylenes substituted in the ortho-position with tethered amide functionality were prepared in a few steps from readily available starting materials. It was found that 5% Pd(OAc)(2)(PPh3)(2) and KOH most effectively promoted cyclization. When the tethered group is an acetamide and an alkyl substituent is on the acetylene unit, regioselective 3-benzazepinone synthesis could be achieved in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.198
• 作为产物：
  描述：

  2-碘苯乙酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-(2-iodophenyl)-N-phenylacetamide
  参考文献：
  名称：

  通过高选择性碳亲核分子途径金催化二聚反应合成2-苯基萘。

  摘要：

  已经开发了用于容易地合成2-苯基萘的方案。在酰胺氮和乙酸氧的存在下，苄基碳充当亲核中心，通过反应物的二聚作用选择性地形成萘骨架。

  DOI：

  10.1021/jo200352j

文献信息

• Branch-Selective Synthesis of Oxindole and Indene Scaffolds: Transition Metal-Controlled Intramolecular Aryl Amidation Leading to C3 Reverse-Prenylated Oxindoles
  作者：Vasily A. Ignatenko、Nihal Deligonul、Rajesh Viswanathan

  DOI：10.1021/ol1012372

  日期：2010.8.20

  a concise branch-selective synthesis of C3 tertiary oxindoles by Cu(I)-catalyzed aryl amidation and 2,2-dimethyl indene by Pd(0)-catalyzed Heck cyclization has been accomplished from acyclic reverse-prenylated intermediates. Oxindole C3-enolate generation using NaH followed by alkylation in the presence of appropriate electrophiles provides a novel route to quaternary C3 reverse-prenylated oxindoles

  为了获得生物学上重要的支架，已通过无环逆反应完成了由Cu（I）催化的芳基酰胺化和Pd（0）催化的Heck环化形成的2,2-二甲基茚的简明的C3叔羟吲哚的支链选择性合成-烯丙基化的中间体。使用NaH生成羟吲哚C3-烯醇盐，然后在适当的亲电试剂存在下进行烷基化，为制备季C3反向预炔化的羟吲哚提供了一条新颖的途径。
• 2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions
  作者：Roberto Frutos-Pedreño、José-Antonio García-López

  DOI：10.1002/adsc.201600224

  日期：2016.8.18

  The synthesis of biologically relevant homophthalimide and 3‐aminoisocoumarin nuclei via palladium‐catalyzed carbonylation of 2‐(2‐iodoaryl)acetamides has been developed. The degree of N‐substitution on the starting amide substrate dictates whether C−N or C−O coupling takes place in the final step of the catalytic cycle giving rise to each type of heterocycle. The introduction of a second C−halogen

  已经开发了通过钯催化的2-（2-碘代芳基）乙酰胺的羰基合成生物相关的邻苯二甲酰亚胺和3-氨基异香豆素核。起始酰胺底物上的N取代程度决定了是在催化循环的最后一步中发生C偶联还是C偶联，从而产生了每种类型的杂环。在起始乙酰胺中引入第二个C-卤素键可进行涉及CH-H活化步骤的催化级联双羰基化反应，从而生成稠合的杂环结构。
• KO^<i>t</i>Bu Mediated Synthesis of Phenanthridinones and Dibenzoazepinones
  作者：Bhagat Singh Bhakuni、Amit Kumar、Shah Jaimin Balkrishna、Javeed Ahmed Sheikh、Sanjit Konar、Sangit Kumar

  DOI：10.1021/ol301077y

  日期：2012.6.1

  Synthesis of substituted phenanthridinones and dibenzoazepinones has been realized from 2-halo-benzamides in the presence of potassium tert-butoxide and a catalytic amount of 1,10-phenanthroline or AIBN. This new carbon–carbon bond forming reaction gives direct access to various biaryl lactams containing six- and seven-membered rings chemoselectively. Carbon–carbon coupling seems to proceed by the generation

  在叔丁醇钾和催化量的1,10-菲咯啉或AIBN的存在下，由2-卤代苯甲酰胺合成了取代的菲啶酮和二苯并a庚酮。这种新的碳-碳键形成反应可直接接近具有化学选择性的六元和七元环的各种联芳基内酰胺。碳-碳偶合似乎是通过酰胺环中自由基的产生而进行的，从而导致苯胺的CH芳基化。
• Organocatalytic synthesis of (Het)biaryl scaffolds <i>via</i> photoinduced intra/intermolecular C(sp²)–H arylation by 2-pyridone derivatives
  作者：Tapas Kumar Das、Mrinalkanti Kundu、Biswajit Mondal、Prasanjit Ghosh、Sajal Das

  DOI：10.1039/d1ob01798e

  日期：——

  O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)–H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic

  一种独特的N , O -二齿配体 6-oxo-1,6-dihydro-pyridone-2-carboxy acid dimethylamide ( L1 ) 催化直接 C(sp 2 )-H (intra/intermolecile) 芳烃芳基化在室温下的紫外线照射下加快获得 (Het) 联芳基支架。该协议容忍不同的功能组和替代模式，以中等至优异的产量提供目标产品。还进行了机理研究以更好地了解反应途径。此外，通过构建生物学相关的 4-喹诺酮、三环内酰胺和磺胺衍生物，展示了这种统一方法的合成适用性。
• Synthesis of Carbocyclic and Heterocyclic Fused Quinolines by Cascade Radical Annulations of Unsaturated <i>N</i>-Aryl Thiocarbamates, Thioamides, and Thioureas
  作者：Wu Du、Dennis P. Curran

  DOI：10.1021/ol0344319

  日期：2003.5.1

  [GRAPHICS]Tandem radical cyclizations of suitably substituted N-aryl thiocarbamates, thioamides, and thioureas are induced by exposure to tris(trimethylsilyl)silane (TTMSH) and UV light and provide furoquinolines, isofuroquinolines, cyclopentaquinolines, indoloquinollnes, and related ring systems. The intermediacy of an alpha-thioalkylamino radical, which is the synthetic equivalent of an imidoyl radical, is invoked.