1,1-二苯基-2-硫氰基乙醇 | 61807-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,1-二苯基-2-硫氰基乙醇
• 英文名称: 1,1-diphenyl-2-thiocyanatoethan-1-ol
• 英文别名: (2-Hydroxy-2,2-diphenylethyl) thiocyanate
• CAS: 61807-33-8
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: BTGSMYRGDZXJHT-UHFFFAOYSA-N

物化性质

• 沸点：
  449.9±45.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-thiocyanatoethene-1,1-diyl)dibenzene 生成 1,1-二苯基-2-硫氰基乙醇
  参考文献：
  名称：

  假卤素化学。三、氯化硫氰原杂裂加成与一些不对称烯烃的取向

  摘要：

  硫氰氯化物与各种不对称烯烃、环烯烃和 α-芳基烯烃在自由基抑制剂的存在下，在 25 °C 的醋酸中，在黑暗中反应生成 α-氯-β-硫氰酸酯、α-乙酰氧基-β-硫氰酸酯、α -羟基-β-硫氰酸酯、乙烯基硫氰酸酯或烯丙基异硫氰酸酯的各种组合。α-芳基烯烃的加成是区域专一性的，产生 Markownikov 取向的产物，但脂肪族烯烃加成的区域专一性取决于烯烃的结构。对于α-芳基烯烃，根据开环碳正离子（例如17）和脂族烯烃的氰基锍离子（例如18）讨论加成方向。

  DOI：

  10.1246/bcsj.49.2310

文献信息

• Photocatalytic anion oxidation achieves direct aerobic difunctionalization of alkenes leading to β -thiocyanato alcohols
  作者：Wei Zhang、Jun-Tao Guo、Yue Yu、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2018.05.007

  日期：2018.6

  extra reducing agent and the new CS and CO bonds could be constructed in one pot. Molecular oxygen not only was used as an excellent terminal oxidant, but also served as a green oxygen source, which is one of the most ideal processes to realize CH bond oxidation functionalization. Moreover, the reaction also proceeded very well under irradiation of sunlight.

  首次描述了通过烯烃双官能化合成β-硫氰酸根合醇的新型可见光驱动氧化级联反应。在该方案中，采用玫瑰红作为光催化剂介导单电子转移，通过光催化将无机离子硫氰酸盐成功转化为自由基。该羟基化过程不需要额外的还原剂，并且可以在一个罐中构建新的C S和C O键。分子氧不仅用作极好的末端氧化剂，而且还用作绿色的氧源，这是实现C H键氧化功能的最理想方法之一。此外，该反应在阳光照射下也进行得很好。
• Photoinduced cascade cyclization of alkynes with NH₄SCN: access to SCN-containing dibenzazepines or dioxodibenzothiazepines
  作者：Shiliu Chen、Qinqin Yan、Jie Fan、Yongjun Gao、Xiulong Yang、Lijun Li、Zhongquan Liu、Zejiang Li

  DOI：10.1039/d2gc01276f

  日期：——

  Photoinduced radical cascade cyclization of aryl acetylenes with NH4SCN was achieved, which provides a simple and mild protocol for the synthesis of SCN-containing dibenzazepines or dioxodibenzothiazepines. A variety of scaled-up operations, functional group transformations, radical capture studies and on/off light experiments were performed to test the merits of the desired products and the reaction

  实现了芳基乙炔与 NH 4 SCN 的光诱导自由基级联环化，为合成含 SCN 的二苯并二氮杂或二氧代二苯并硫氮杂提供了一种简单而温和的方案。进行了各种放大操作、官能团转换、自由基捕获研究和开/关光实验，以测试所需产物和反应过程的优点。
• Diquat Based Dyes: A New Class of Photoredox Catalysts and Their Use in Aerobic Thiocyanation
  作者：Armin Meier、Sabuhi V. Badalov、Timur Biktagirov、Wolf Gero Schmidt、René Wilhelm

  DOI：10.1002/chem.202203541

  日期：——

  From diquat to dye-cat. A series of push–pull dyes using diquat as the electron-acceptor moiety have been synthesized. Their photocatalytic abilities were tested in the aerobic thiocyanation of indoles and pyrroles, giving yields of up to 97 %.

  从敌草快到染料猫。已经合成了一系列使用敌草快作为电子受体部分的推挽染料。他们的光催化能力在吲哚和吡咯的有氧硫氰化反应中进行了测试，产率高达 97%。
• 1,1-Diphenyl-2-methylsulfinyl ethanol: a model compound to study the reactivity towards CNBr of a photoadduct of methionine on CγH2
  作者：Emmanuelle Sachon、Thierry Milcent、Sandrine Sagan、Odile Convert、Gérard Chassaing、Solange Lavielle

  DOI：10.1016/s0040-4039(02)01801-4

  日期：2002.10

  The photoadduct formed by photolysis of the [Bapa(0), (pBzl)Phe(5), Met(O-2)(11)]SP/NK-1 complex localised within the (TMP175)-M-173 domain of the NK-1 receptor cannot be cleaved by CNBr on the C-side of methionine; an unusual rearrangement of the intermediate sulfonium instead Occurred. The reactivity of 1,1-diphenyl-2-methylsulfinyl ethanol 10 towards CNBr treatment and the stability of the 1,1-diphenyl oxirane 14 were analysed by NMR and mass spectrometry. 1,1-Diphenyl ethylene 13 can be formed from epoxide 14 even in slightly acidic conditions and during positive DCI/NH3 mass spectrometry analysis. Altogether, these results suggest that if a covalent linkage between the [Bapa(0), (pBzl)Phe(5), Met(O-2)(11)] and the NK-1 receptor occurred on the CyH2 of methionine-174, CNBr treatment will lead to an epoxide/ketone and an ethylenic compound. (C) 2002 Published by Elsevier Science Ltd.