10-iodophenanthrene-9-carbonitrile | 172878-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 10-iodophenanthrene-9-carbonitrile
• 英文别名: 9-Cyano-10-iodophenanthrene
• CAS: 172878-79-4
• 化学式: C₁₅H₈IN
• 分子量: 329.14
• InChiKey: PCKPVBKGGWWFAP-UHFFFAOYSA-N

物化性质

• 沸点：
  484.6±28.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  10-iodophenanthrene-9-carbonitrile 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 以83%的产率得到9-Carboxamido-10-iodophenanthrene
  参考文献：
  名称：

  9-Iodoso-10-phenanthroate: Structure and Phosphorolytic Properties of a Nonplanar Iodoxolone

  摘要：

  9-Iodoso-10-phenanthroic acid (IPA-OK) was prepared from 9-cyanophenanthrene in a four-step, 44% overall yield synthesis, featuring cyano-directed ortho lithiation/iodination as the key step. An X-ray crystal structure showed that TPA-OH exists in a phenanthroiodoxol-3(1H)-one valence tautomeric form, 14-OH, characterized by T-shaped geometry at iodine, strong WO steric interactions between the peri-H atoms and the carbonyl and iodoso oxygen atoms, a ''short'' endocyclic I-O bond, well-differentiated carbonyl and endocyclic C-O bond lengths, and nonplanarity in both the iodoxolone and phenanthrene rings (Figures 1 and 2). IPA-OH was an excellent catalyst for the cleavage of p-nitrophenyl diphenyl phosphate (PNPDPP) in aqueous micellar cetyltrimethylammonium chloride (CTACl) solutions at pH 8 and 25 degrees C: 1 x 10(-5) M PNPDPP was cleaved by 1 x 10(-4) M IPA-OH in 3.5 x 10(-4) M CTACl with k(psi) = 0.38 s(-1). Experiments in which [PNPDPP] > [IPA-OH] demonstrated that the catalyst ''turned over''; hydrolysis of the putative phosphorylated IPA-OH intermediate was rapid.

  DOI：

  10.1021/jo00129a012
• 作为产物：
  描述：

  9-腈菲 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 碘 作用下， 以60%的产率得到10-iodophenanthrene-9-carbonitrile
  参考文献：
  名称：

  腈的Carpalpalladation：由Pd催化的2-碘亚芳基腈对炔烃和双环烯烃的环化反应合成2，3-二芳基萘酮和多环芳族酮。

  摘要：

  2-碘苄腈，其衍生物和各种杂环类似物在二芳基乙炔或双环烯烃上进行钯（0）催化的环化反应，从而以非常好的至极好的收率得到2,3-二芳基萘和多环芳族酮。该反应代表将有机钯部分加成到腈的碳-氮三键上的第一个例子。该反应与许多官能团相容。提出了反应机理以及考虑取代基对腈芳环电子效应的模型。

  DOI：

  10.1021/jo026178g

文献信息

• Transition-Metal-Free Cross-Coupling of Aryl and <i>N</i>-Heteroaryl Cyanides with Benzylic Zinc Reagents
  作者：Pauline Quinio、Daniela Sustac Roman、Thierry León、Sharankini William、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1021/acs.orglett.5b02380

  日期：2015.9.4

  Functionalized 4-benzylated pyridines can be efficiently prepared by a transition-metal-free cross-coupling between various benzylic zinc chlorides and substituted 4-cyanopyridines in THF/DMPU under microwave irradiation (40 °C, 0.5–1.5 h). Selective benzylations on polycyano-aromatics have also been achieved under these mild conditions. We also report a novel oxidative nucleophilic substitution of

  通过在微波辐射（40°C，0.5-1.5 h）下，各种苄基氯化锌与取代的4-氰基吡啶在THF / DMPU中的无过渡金属交叉偶联，可以有效地制备功能化的4-苄基吡啶。在这些温和的条件下，还可以实现多氰基芳族化合物的选择性苄基化。我们还报告了一种使用苄基锌试剂在1,3-二氰基苯上氢的新型氧化亲核取代反应。
• Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with <i>o</i>-Halonitroarenes or <i>o</i>-Iodobenzonitriles and Reductive Cyclization of the Resulting Products To Give Diverse Heterocyclic Systems
  作者：Faiyaz Khan、Michael Dlugosch、Xin Liu、Marium Khan、Martin G. Banwell、Jas S. Ward、Paul D. Carr

  DOI：10.1021/acs.orglett.8b01015

  日期：2018.5.4

  palladium-catalyzed Ullmann cross-coupling of β-iodoenones and β-iodoacrylates such as 5 (X = I) with o-halonitroarenes and o-iodobenzonitriles including 2 affords products such as compound 7. These can be engaged in a range of reductive cyclization reactions leading to heterocyclic frameworks such as 3,4-benzomorphan derivative 43.

  钯催化的β-碘烯酮和β-碘丙烯酸酯（如5（X = I））与邻卤代硝基芳烃和邻碘碘苄腈（包括2种）的Ullmann交叉偶联提供了化合物（如化合物7）。这些可以参与一系列还原性环化反应，从而形成杂环骨架，例如3,4-苯并吗啡衍生物43。