2'-iodo-[1,1'-biphenyl]-2-carbonitrile | 36271-73-5

• 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'-iodo-[1,1'-biphenyl]-2-carbonitrile
• 英文别名: 2'-iodobiphenyl-2-carbonitrile；2-cyano-2'-iodobiphenyl；2-(2-Iodophenyl)benzonitrile
• CAS: 36271-73-5
• 化学式: C₁₃H₈IN
• 分子量: 305.118
• InChiKey: IPHNMYFCSQUHGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  413.6±38.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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'-iodo-[1,1'-biphenyl]-2-carbonitrile 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以34%的产率得到菲啶
  参考文献：
  名称：

  Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-H-Phenanthridines via a Transition-Metal-Free Process

  摘要：

  A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.

  DOI：

  10.1021/acs.orglett.5b00544
• 作为产物：
  描述：

  2-氰基联苯 在 tetrafluoroboric acid 、 bis(pyridine)iodonium tetrafluoroborate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 以44%的产率得到2'-iodo-[1,1'-biphenyl]-2-carbonitrile
  参考文献：
  名称：

  无金属 DirectedorthoC-H 碘化：合成 2'-Iodobiaryl-2-carbonitriles

  摘要：

  开发了联芳基-2-腈的无金属定向邻位 C-H 碘化。使用双（吡啶）碘鎓（I）四氟硼酸盐（IPy2BF4，Barluenga 试剂）和 HBF4·OEt2，从取代的联苯甲腈和萘基苄腈合成了一系列 2'-碘联二芳基-2-甲腈，收率相当好。联芳基-2-腈是合成苯环酮的有用前体。

  DOI：

  10.1002/ejoc.201300584

文献信息

• Carbopalladation of Nitriles:  Synthesis of Benzocyclic Ketones and Cyclopentenones via Pd-Catalyzed Cyclization of ω-(2-Iodoaryl)alkanenitriles and Related Compounds
  作者：Alexandre A. Pletnev、Richard C. Larock

  DOI：10.1021/jo0262006

  日期：2002.12.1

  An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This methodology has been extended to the synthesis of tetralones and cyclopentenones.

  已经开发出一种通过腈的分子内碳弹头化合成2，2-二取代的苯并环酮的有效方法。取代的3-（2-碘芳基）丙烷腈的环化以高收率提供茚满酮。该反应与多种官能团相容。该方法已经扩展到四氢萘酮和环戊烯酮的合成。
• Iodine-mediated aryl transfer reaction from arylhydrazine hydrochlorides to nitriles
  作者：Zhiguo Zhang、Xiang Li、Yinghua Li、Yan Guo、Xunan Zhao、Yan Yan、Kai Sun、Guisheng Zhang

  DOI：10.1016/j.tet.2019.05.034

  日期：2019.6

  An iodine-promoted, metal-, base-, and solvent-free cross-coupling reaction was developed for the synthesis of various useful secondary amides via an aryl N-addition reaction of aryl groups to cyano groups. This aryl transfer reaction proceeds with arylhydrazine hydrochlorides serving as the aryl donors. A labelling experiment shows that the N atom in the product comes from the cyano group of the nitriles

  通过芳基与氰基的芳基N加成反应，开发了碘促进的，无金属，无碱和无溶剂的交叉偶联反应，用于合成各种有用的仲酰胺。该芳基转移反应与用作芳基供体的芳基肼盐酸盐一起进行。标记实验表明，产物中的N原子来自腈的氰基，它们的成本较低。还提出了一种可行的自由基驱动机制。
• Synthesis of benzocyclic ketones via palladium-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles
  作者：Alexandre A. Pletnev、Richard C. Larock

  DOI：10.1016/s0040-4039(02)00247-2

  日期：2002.3

  An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This chemistry has been extended to the synthesis of tetralones, a 9-fluorenone and a cyclopentenone

  已经开发了一种通过腈的分子内碳弹孔法合成2,2-二取代的苯并环酮的有效方法。取代的3-（2-碘芳基）丙腈的环化以高收率提供茚满酮。该反应与多种官能团相容。该化学反应已扩展到四氢萘酮，9-芴酮和环戊烯酮的合成。
• Polycyclic biphenylenes. Part IV. Biphenylenes derived from 9,10-phenanthryne
  作者：J. W. Barton、A. R. Grinham

  DOI：10.1039/p19720000634

  日期：——

  10-phenanthryne (II) were obtained but the dimer of (II), tetrabenzo[a,c,g,i]biphenylene (III), was not found. ‘Crossed’ aryne couplings of (II) with benzyne and 2,3-naphthalyne gave dibenzo[a,c]- and tribenzo[a,c,h]-biphenylene; that with 1,2-naphthalyne failed. The results are discussed with regard to the stabilities of these annelated biphenylenes.

  苯并[9,10- d ]三唑的胺化反应生成1-氨基-1 H-和2-氨基-2 H-衍生物[（I; R = NH 2）和（V）]的混合物，其中后者占主导地位。在用四乙酸铅氧化化合物（I; R = NH 2）中，获得了衍生自9,10菲炔（II）的产物，但（II）的二聚体是四苯并[ a，c，g，i ]联苯（III），未找到。（II）与苯炔和2,3-萘的“交叉”芳烃偶合得到二苯并[ a，c ]-和三苯并[ a，c，h]-联苯; 带有1,2-萘的化合物失效。就这些退火的联苯的稳定性讨论了结果。
• Synthesis of Polysubstituted Phenanthridines via Ligand-Free Copper-Catalyzed Annulation
  作者：Yan-Fu Chen、Jen-Chieh Hsieh

  DOI：10.1021/ol502237a

  日期：2014.9.5

  A novel procedure for the cascade reaction of the addition of a Grignard reagent to a nitrile with a copper-catalyzed C-N bond coupling was developed, which afforded various polysubstituted phenanthridines in moderate to good yields with tolerance for a wide variety of substrates. Experimental data demonstrated that the reaction proceeded more likely through a Cu(I/III) catalytic cycle.