2-selenocyanatobenzaldehyde | 36898-58-5

• 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-selenocyanatobenzaldehyde
• 英文别名: 2-Formylphenyl selenocyanate；(2-formylphenyl) selenocyanate
• CAS: 36898-58-5
• 化学式: C₈H₅NOSe
• 分子量: 210.094
• InChiKey: MATIJAULRDHFHG-UHFFFAOYSA-N

物化性质

• 沸点：
  328.1±44.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium sulfide 、 2-selenocyanatobenzaldehyde 、 nickel diacetate 、 C.I.酸性橙108 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Garnovskii, A. D.; Kochin, S. G.; Vasil'chenko, I. S., Journal of General Chemistry of the USSR, 1989, vol. 59, p. 2499 - 2499

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(o-formylphenyl) diselenide 在 磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-selenocyanatobenzaldehyde
  参考文献：
  名称：

  Nature of Nonbonded Se···O Interactions Characterized by ¹⁷O NMR Spectroscopy and NBO and AIM Analyses

  摘要：

  To investigate the nature of nonbonded (SeO)-O-... interactions, three series of 2-substituted benzeneselenenyl derivatives [2-(CHO)C6H4SeX (1), 2-(CH2OH)C6H4SeX, (2), 2-(CH(2)OiPr)C6H4SeX (3); X = Cl, Br, CN, SPh, SeAr, Me] were synthesized. The O-17 NMR absorption observed for O-17-enriched aldehydes 1 appeared upfield relative to benzaldehyde (PhCHO), while the opposite downfield shifts relative to benzyl alcohol (PhCH2OH) were observed for O-17-enriched alcohols 2 and ethers 3. The magnitude of both the upfield and the downfield shifts became larger as the electron-withdrawing ability of a substituent X increased. Quantum chemical calculations at the B3LYP level revealed that for all model compounds the most stable conformer has an intramolecular nonbonded (SeO)-O-... interaction. Thus, the relative O-17 NMR chemical shifts (Deltadelta(o)) for 1-3 would reflect the strengths of the (SeO)-O-... interactions. The natural bond orbital (NBO) analysis demonstrated that the stabilization energy due to an no --> sigma(Se-X)(*) orbital interaction ((ESeO)-O-...) correlates with the (SeO)-O-... atomic distance on a single curve irrespective of the type of the O atom. On the other hand, the atoms in molecules (AIM) analysis showed that the nonbonded (SeO)-O-... interactions can be characterized by the presence of a bond critical point, the total energy density ((HSeO)-O-...) of which decreases with strengthening of the interaction. The results suggested that (SeO)-O-... interactions have a dominant covalent character rather than an electrostatic one.

  DOI：

  10.1021/ja049690n

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。
• Thianthrene Radical Cation as a Transient<scp>SET</scp>Mediator: Photoinduced Thiocyanation and Selenocyanation of Arylthianthrenium Salts^†
  作者：Xiao‐Yue Chen、Xin Kuang、Yichen Wu、Jian Zhou、Peng Wang

  DOI：10.1002/cjoc.202300188

  日期：2023.8.15

  A novel transient SET mediator approach has been developed for the photoinduced radical-radical cross coupling reaction. Using the in-situ generated thianthrene radical cation as the transient SET mediator, the thiocyanation and selenocyanation of aryl thianthrenium salts have been realized under the mild conditions without the need for photocatalyst or single electron donor. In comparison with the

  一种新型瞬态 SET 介体方法已被开发用于光诱导自由基-自由基交叉偶联反应。利用原位产生的噻蒽自由基阳离子作为瞬态SET介体，在温和条件下实现了芳基噻蒽鎓盐的硫氰化和硒氰化，无需光催化剂或单一电子给体。与光触媒工艺相比，该方案具有条件温和、操作简单、底物范围广泛、优异的官能团和杂环耐受性等特点。由于芳基噻啉鎓盐的可行可及性，该方法也已应用于生物活性分子的有效合成以及复杂芳烃的后期功能化。