(thiocyanato)(diphenyl)methane | 13317-56-1

• 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: (thiocyanato)(diphenyl)methane
• 英文别名: (thiocyanatomethylene)dibenzene；Diphenylmethyl-thiocyanat；Diphenylmethylthiocyanat；Benzhydryl-thiocyanat；Benzhydrylthiocyanat；Benzhydryl thiocyanate
• CAS: 13317-56-1
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: SBWAWGPWUHYFRI-UHFFFAOYSA-N

物化性质

• 熔点：
  58.5-59 °C(Solv: ligroine (8032-32-4))
• 沸点：
  160-170 °C(Press: 2 Torr)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (thiocyanato)(diphenyl)methane 以 乙腈 为溶剂， 生成 二苯甲基异硫氰酸盐
  参考文献：
  名称：

  Iliceto,A. et al., Gazzetta Chimica Italiana, 1960, vol. 90, p. 919 - 940

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基甲烷 生成 (thiocyanato)(diphenyl)methane
  参考文献：
  名称：

  Barton Derek H. R., Chavasiri Warinthorn, Tetrahedron, 50 (1994) N 1, S 47-60

  摘要：

  DOI：

文献信息

• Kinetics of the reactions of laser-flash photolytically generated carbenium ions with alkyl and silyl enol ethers. Comparison with the reactivity toward alkenes, allylsilanes and alcohols
  作者：Joerg Bartl、Steen Steenken、Herbert Mayr

  DOI：10.1021/ja00020a038

  日期：1991.9

  corresponding alkyl-substituted ethylenes. The reactivities of structurally analogous alkyl and silyl enol ethers differ by less than 1 order of magnitude. In sharp contrast to the situation previously observed for the reactions of benzhydryl cations with alkenes, the nucleophilic reactivities of the enol ethers correlate with their ionization potentials and not with the stabilities of the carbenium ions

  二芳基碳鎓离子（二苯甲基阳离子）是在 20 OC 的乙腈溶液中通过 20-11 秒激光脉冲 (248 nm) 从二芳基甲基氯生成的。它们与 n 和 w 亲核试剂（阴离子、醇、水、烯烃、烯丙基硅烷、烷基和甲硅烷基烯醇醚）反应的二级速率常数是通过在可变亲核试剂浓度下监测 UV-vis 瞬变的衰减来确定的。由于碳鎓离子与溶剂乙腈和光杂解中产生的氯离子同时发生反应，因此只能通过这种方法研究反应性亲核试剂 (k2 > 106-107 L mol-' sI)。观察到的最大 k2 值为 -2 X 1Olo 与阴离子反应和 (2-4) X IO8, mol-' sI 与中性亲核试剂反应。烷氧基取代的乙烯的反应性比相应的烷基取代的乙烯高 300-1 倍。结构相似的烷基和甲硅烷基烯醇醚的反应性相差不到 1 个数量级。与之前观察到的二苯甲基阳离子与烯烃反应的情况形成鲜明对比的是，烯醇醚的亲核反应性与其电离电位相
• Nucleophilic Substitution Reactions of Alkyl Halides by Using New Polymer-Supported Reagents Containing Hemin
  作者：Kiyoshi Saito、Kaoru Harada

  DOI：10.1246/bcsj.62.2562

  日期：1989.8

  hemin, divinylbenzene, and 2-methyl-5-vinylpyridine was synthesized by suspension copolymerization. Substitution reactions of primary, secondary, and tertiary alkyl halides with the hemin copolymer combined with cyanide, azide, and thiocyanate ions were given satisfactory yields. This reaction mechanism was revealed to be a SNi type on the basis of stereochemical study. The hemin copolymer was not only

  通过悬浮共聚反应合成了一种由氯化血红素、二乙烯基苯和2-甲基-5-乙烯基吡啶组成的新型高分子试剂。伯、仲和叔烷基卤与氯化血红素共聚物与氰化物、叠氮化物和硫氰酸根离子的取代反应得到了令人满意的产率。根据立体化学研究，该反应机理被揭示为 SNi 型。氯化血红素共聚物不仅是具有功能性的聚合物负载试剂，而且还用于将产物与反应混合物分离。
• A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers
  作者：Nasser Iranpoor、Habib Firouzabadi、Roya Azadi

  DOI：10.1016/j.tetlet.2006.05.145

  日期：2006.7

  A new diphenylphosphinite ionic liquid (IL-OPPh2) is introduced. This ionic liquid is used as both a reagent and a solvent to convert alcohols and trimethylsilyl and tetrahydropyranyl (THP) ethers into their corresponding alkyl bromides, thiocyanates or isothiocyanates in the presence of Br2 and SCN− at 80 °C. In this ionic liquid, bromination and thiocyanation of alcohols occurs highly selectively

  介绍了一种新型的二苯基次膦酸酯离子液体（IL-OPPh 2）。这种离子液体用作两者的试剂和转换醇和三甲基甲硅烷和四氢吡喃基（THP）溶剂醚类为它们相应的烷基溴化物，硫氰酸盐或异硫氰酸盐在溴的存在下2和SCN -在80℃下。在这种离子液体中，在三甲基甲硅烷基和THP-醚的存在下以及在不同类别的醇之间，醇的溴化和硫氰化反应会高度选择性地发生。该离子液体的使用使得所需的产物易于从次膦酸酯副产物中分离出来。
• AIBN-initiated direct thiocyanation of benzylic sp³ C–H with <i>N</i>-thiocyanatosaccharin
  作者：Di Wu、Yongjie Duan、Kun Liang、Hongquan Yin、Fu-Xue Chen

  DOI：10.1039/d1cc04302a

  日期：——

  Direct thiocyanations of benzylic compounds have been implemented. Here, a new strategy, involving a free radical reaction pathway initiated by AIBN, was used to construct the benzylic sp3 C–SCN bond. In this way, the disadvantage of other strategies involving introducing leaving groups in advance to synthesize benzyl thiocyanate compounds was overcome. The currently developed protocol also involved

  已经实施了苄类化合物的直接硫氰化。在这里，涉及由 AIBN 引发的自由基反应途径的新策略用于构建苄型 sp 3 C-SCN 键。通过这种方式，克服了其他涉及提前引入离去基团以合成硫氰酸苄酯化合物的策略的缺点。目前开发的协议还涉及使用现成的原材料，并导致高产率（高达 100%），这两者都是合成硫氰酸苄酯的巨大优势。
• Preparation of thiocyanates and isothiocyanates from alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/n-Bu4NSCN system
  作者：Nasser Iranpoor、Habib Firouzabadi、Najmeh Nowrouzi

  DOI：10.1016/j.tet.2006.03.030

  日期：2006.6

  A combination of triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) provides a safe and easily available mixed reagent system for the conversion of 1° and 2° alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers to their corresponding thiocyanates and the 3° ones to isothiocyanates in good to high yields.

  三苯基膦（PPh 3）和2,3-二氯-5,6-二氰基苯并醌（DDQ）的组合提供了一种安全且易于使用的混合试剂体系，可用于转化1°和2°醇，硫醇，三甲基甲硅烷基和四氢吡喃基醚转化为相应的硫氰酸酯，3°异构化为异硫氰酸酯，收率高至高。