2-ethyl-2-(2-iodophenyl)butanenitrile | 219678-95-2

• 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-ethyl-2-(2-iodophenyl)butanenitrile
• CAS: 219678-95-2
• 化学式: C₁₂H₁₄IN
• 分子量: 299.154
• InChiKey: RNMMQIZGYYSQEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethyl-2-(2-iodophenyl)butanenitrile 在 trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II) 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.25h， 生成 2-(2'-aminobiphen-2-yl)-2-ethylbutyronitrile
  参考文献：
  名称：

  Antimitotic agents interacting with tubulin: Synthesis and structure-activity relationships of novel ortho bridged biphenyls of the rhazinilam type

  摘要：

  Several new ortho bridged biphenyls mimicking the structure of (-)-rhazinilam were synthesized and evaluated as cytotoxic compounds and as inhibitors of microtubules disassembly. These included azadibenzo[a,c]cyclononene derivatives having an ester, urea or carbamate function present in the 9-membered ring linking the two phenyl moieties. The compound bearing a carbamate function instead of the amide group of rhazinilam interacts better with tubulin than (-) rhazinilam, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00903-x
• 作为产物：
  描述：

  2-碘苯基乙腈 、 碘乙烷 在 sodium t-butanolate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 以92%的产率得到2-ethyl-2-(2-iodophenyl)butanenitrile
  参考文献：
  名称：

  6-Membered Pseudocyclic IBX Acids: Syntheses, X-ray Structural Characterizations, and Oxidation Reactivities in Common Organic Solvents

  摘要：

  We designed and synthesized lambda(5)-cyclic periodinanes 1 and 2, which are homologous to IBX (1-hydroxyl-oxo-1H-1 lambda(5)-benzo[d][1,2]iodoxol-3-one) by one carbon, to thwart close packing of molecules in the crystal lattice to permit solubility in common organic solvents and to facilitate oxidations with enhanced reactivity. The X-ray crystal structures revealed that both 1 and 2 exist in the solid state as pseudocyclic (PC) acids, i.e., 1PC and 2PC, and that the molecules in the lattice are less weakly associated as compared to those in the parent IBX due to the twisting introduced via the sp(3) benzylic carbon. Both 1PC and 2PC are found to dissolve in palpable amounts in DCM and acetonitrile to allow oxidation of a variety of alcohols and sulfides to carbonyl compounds and sulfoxides in a facile manner. The subtle differences in the sterics due to methyl and ethyl substituents in 1PC and 2PC are found to manifest in contrasting reactivities in that the oxidations of alcohols occur faster with 2PC, while those of sulfides to sulfoxides occur more rapidly with 1PC.

  DOI：

  10.1021/jo101639j

文献信息

• Application of the Palladium-Catalyzed Borylation/Suzuki Coupling (BSC) Reaction to the Synthesis of Biologically Active Biaryl Lactams
  作者：Olivier Baudoin、Michèle Cesario、Daniel Guénard、Françoise Guéritte

  DOI：10.1021/jo0160726

  日期：2002.2.1

  The palladium-catalyzed, two-step, one-pot borylation/Suzuki coupling (BSC) reaction was developed to synthesize sterically hindered 2,2'-disubstituted biphenyl and phenyl-indole compounds in a short, simple, and efficient manner from two easily accessible aryl halides. High yields can be obtained by choosing properly both components according to their rough electronic properties. The illustration

  开发了钯催化的两步一锅法硼化/铃木偶联（BSC）反应，以短短，简单和有效的方式从两个容易的位置合成空间位阻的2,2'-二取代联苯和苯基吲哚化合物可及的芳基卤化物。高的产率可通过根据它们的粗糙电子性质适当选择这两种组分来获得。通过七元或八元联苯内酰胺5a-e和paullone 3a的溶液和固相合成，提供了该方法实用性的说明。这些化合物尽管具有明显的细胞毒性，但仍具有中等程度的毒性，并可作为未来药物化学发展的结构模型。
• Palladium-Catalyzed Borylation of Ortho-Substituted Phenyl Halides and Application to the One-Pot Synthesis of 2,2‘-Disubstituted Biphenyls
  作者：Olivier Baudoin、Daniel Guénard、Françoise Guéritte

  DOI：10.1021/jo005663d

  日期：2000.12.1