2-selenocyanobiphenyl | 129922-48-1

• 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-selenocyanobiphenyl
• 英文别名: o-selenocyanobiphenyl；2-selenocyanato-1,1'-biphenyl；biphenyl-2-yl selenocyanate；Selenocyansaeure-(biphenylyl-(2)-ester)；Biphenyl-2-ylselenocyanat；2-Selenocyanato-biphenyl；(2-Phenylphenyl) selenocyanate
• CAS: 129922-48-1
• 化学式: C₁₃H₉NSe
• 分子量: 258.181
• InChiKey: CWWJYSUIRICUHD-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C(Solv: acetic acid (64-19-7))
• 沸点：
  200-202 °C(Press: 15 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  15
• 可旋转键数：
  2
• 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-selenocyanobiphenyl 在 sodium tetrahydroborate 、 fluorine 作用下， 以 一氟三氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(三氟甲基)二苯并[b,d]硒吩鎓三氟甲烷磺酸酯
  参考文献：
  名称：

  功率可变的亲电三氟甲基化剂。S-、Se-和Te-(三氟甲基)二苯并硫代-、-硒-和-碲鎓盐系统

  摘要：

  S-、Se-和 Te-三氟甲基化二苯并杂环鎓盐、它们的衍生物和相关盐是通过 2-[（三氟甲基）硫代或硒代]联苯和三氟甲磺酸 (TfOH) 或 HBF 的混合物的直接氟化合成的4 醚化物，通过使用 Tf 2 O 和 (CH 3 ) 2 SO 对 2-[(三氟甲基) 碲] 联苯进行新型碲活化，或通过鎓的衍生，用 Tf 2 O 处理相应的亚砜和硒氧化物得到的盐。反应性检查表明，与非杂环盐相比，三氟甲基杂环盐具有很强的反应性，并表明该杂环盐体系可作为广泛适用的三氟甲基化剂的来源

  DOI：

  10.1021/ja00059a009
• 作为产物：
  描述：

  potassium selenocyanate 、 2-氨基联苯 在 硫酸 、 sodium nitrite 、 sodium acetate 作用下， 以49%的产率得到2-selenocyanobiphenyl
  参考文献：
  名称：

  Deoxygenation and Other Photochemical Reactions of Aromatic Selenoxides¹

  摘要：

  Atomic oxygen O(P-3) is a potent oxidant that has been well-studied in the gas phase. However, exploration of its reactivity in the condensed organic phase has been hampered by the lack of an appropriate source. Dibenzothiophene-S-oxide (DBTO) and related derivatives have been promoted as photochemical O((3)p) sources but suffer from low quantum yields. Photolysis of dibenzoselenophene-Se-oxide (DBSeO) results in the formation of dibenzoselenophene and oxidized solvent in significantly higher quantum yields, ca. 0.1. The oxidation product ratios from toluene obtained from the photolysis of dibenzothiophene- oxide and the corresponding selenoxide are the same, strongly suggesting a common oxidizing intermediate, which is taken to be O((3)p). An additional product, proposed to be the corresponding selenenic ester, is also observed under deoxygenated conditions. The photochemistry of diphenyl selenoxide includes a minor portion of oxidant-forming deoxygenation, in contrast to previous conclusions.

  DOI：

  10.1021/ja045935k

文献信息

• Metal‐Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium
  作者：Xue Zhang、Xiao‐Bo Huang、Yun‐Bing Zhou、Miao‐Chang Liu、Hua‐Yue Wu

  DOI：10.1002/chem.202004005

  日期：2021.1.13

  This work reports a green method for the synthesis of aryl selenocyanates via a three‐component reaction of arylboronic acids, Se powder, and trimethylsilyl cyanide (TMSCN) under metal‐free and additive‐free conditions. Remarkably, TMSCN acts as not only the substrate, but also the catalyst. Various selenaheterocycles can be also accessed with a catalytic amount of TMSCN.

  这项工作报告了一种在无金属和无添加剂条件下通过芳基硼酸，硒粉和三甲基甲硅烷基氰化物（TMSCN）的三组分反应合成芳基硒氰酸酯的绿色方法。显着地，TMCSN不仅充当底物，而且充当催化剂。还可使用催化量的TMSCN来获得各种硒杂环。
• Synthesis of Selenaheterocycles via Visible‐Light‐Mediated Radical Cyclization
  作者：Kim Christopher C. Aganda、Anna Lee

  DOI：10.1002/adsc.202100969

  日期：2021.11.23

  An approach for the synthesis of selenaheterocycles starting from aryl diazonium salts was developed. The one-pot process and subsequent visible-light-mediated silver-catalyzed cyclization enabled the synthesis of selenaheterocycles in the absence of a photocatalyst. The reactions were carried out under mild conditions without the use of toxic or sensitive reagents.

  开发了一种从芳基重氮盐开始合成硒杂环的方法。一锅法和随后的可见光介导的银催化环化能够在没有光催化剂的情况下合成硒杂环。反应在温和条件下进行，没有使用有毒或敏感的试剂。
• Perfluoroalkyl-containing compound
  申请人：Sagami Chemical Research Center

  公开号：US05066795A1

  公开（公告）日：1991-11-19

  A (perfluoroalkyl)dibenzonium salt represented by the following general formula ##STR1## wherein R.sub.f represents a perfluoroalkyl group having 1 to 10 carbon atoms, A represents a sulfur of selenium atom, R.sup.1 and R.sup.2, independently from each other, represent a hydrogen atom or a nitro group, X.sup..crclbar. represents a conjugated base of Bronsted acid, and n is 0 or 1. The said compound is useful as a reagent for introducing a perfluoroalkyl group.

  一种由以下通用公式表示的（全氟烷基）二苯酚盐：其中R.sub.f代表具有1至10个碳原子的全氟烷基基团，A代表硫或硒原子，R.sup.1和R.sup.2分别代表氢原子或硝基基团，X.sup..crclbar.代表布朗斯特酸的共轭碱基，n为0或1。所述化合物可用作引入全氟烷基基团的试剂。
• Power-variable trifluoromethylating agents, (trifluoromethyl)dibenzothio- and -selenophenium salt system
  作者：Umemoto Teruo、Ishihara Sumi

  DOI：10.1016/s0040-4039(00)94447-2

  日期：1990.1
• The Reaction of Aryllithium Compounds with Aryl Selenocyanates. A New Synthesis of Unsymmetric Diaryl Selenides¹
  作者：Bernard Greenberg、Edwin S. Gould、Wm. Burlant

  DOI：10.1021/ja01597a043

  日期：1956.8