Se,Se-dibenzyl triselenocarbonate | 17107-93-6

• 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: Se,Se-dibenzyl triselenocarbonate
• 英文别名: dibenzyl triselenocarbonate；TSC；Triselenokohlensaeure-dibenzylester；Dibenzyl-triselenocarbonat；Dibenzyltriselenocarbonat；Bis(benzylselanyl)methaneselone
• CAS: 17107-93-6
• 化学式: C₁₅H₁₄Se₃
• 分子量: 431.156
• InChiKey: DRZVSCUQLKPFDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  Se,Se-dibenzyl triselenocarbonate 在 potassium hydrogencarbonate 、 mercury dichloride 作用下， 以 水 、 丙酮 为溶剂， 反应 0.08h， 以59%的产率得到Se-Se'-dibenzyl diselenocarbonate
  参考文献：
  名称：

  三硒代碳酸二苄酯与氧碱反应的动力学和机理

  摘要：

  使用KOH，Me 4 NOH，Bu 4 n NOH和Bu 4 n NHCO 3作为碱，通过伪一级反应条件下的紫外分光光度法研究了碱诱导的二硒代三碳酸二苄酯在DMSO /水中的溶剂分解（4：1）。。相对于底物和碱，反应是一级反应。四个碱基的速率常数和激活参数表明速率确定步骤是碱基（作为离子对）在基质上的亲核攻击。由于强烈的亲核性硒酸根类物质，快速反应可能会跟随这一缓慢的步骤。在实验证据的基础上提出了一种试探性的机制。

  DOI：

  10.1016/0040-4020(80)85061-7
• 作为产物：
  描述：

  二硒化碳 、 氯化苄 在 potassium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以37.5%的产率得到Se,Se-dibenzyl triselenocarbonate
  参考文献：
  名称：

  Selenium-substituted carbonates as mediators for controlled radical polymerization

  摘要：

  ABSTRACTA series of selenium‐substituted carbonates, S,Se‐dibenzyl dithioselenocarbonate (DTSC), S,Se‐dibenzyl thiodiselenocarbonate (TDSC), and Se,Se‐dibenzyl triselenocarbonate (TSC), were synthesized and used as mediators in radical polymerization. The results indicate that these selenium‐substituted carbonates can control the polymerization of styrene (St) and methyl acrylate, as evidenced by the number‐average molecular weight that increased linearly with the monomer conversion, molecular weights that agreed well with the predicted values, and successful chain extensions. The treatment of the resultant polystyrene by hydrogen peroxide generated polymers with approximately half‐reduced molecular weights, and the absence of carbonate groups and vinyl double bond‐terminated chain ends. The polymerization with these selenium‐substituted carbonates was the same polymerization mechanism as their analogue, the widely used S,S‐dibenzyl trithiocarbonate. This work provided a flexible protocol to incorporate selenium into the polymer chain backbone. Specifically, the treatment of these polymers by oxidation produced “clickable” vinyl‐terminated chain ends, which provided possibilities for further functionalization, for example, via a thiol‐ene click reaction. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2606–2613

  DOI：

  10.1002/pola.26648

文献信息

• Preparation of Selenoformamides by Selenol Reduction of Dibenzyl Triselenocarbonate¹
  作者：Lars HENRIKSEN

  DOI：10.1055/s-1974-23356

  日期：——
• Selenium-substituted carbonates as mediators for controlled radical polymerization
  作者：Jindong Zeng、Zhengbiao Zhang、Jian Zhu、Nianchen Zhou、Zhenping Cheng、Xiulin Zhu

  DOI：10.1002/pola.26648

  日期：2013.6.15

  ABSTRACTA series of selenium‐substituted carbonates, S,Se‐dibenzyl dithioselenocarbonate (DTSC), S,Se‐dibenzyl thiodiselenocarbonate (TDSC), and Se,Se‐dibenzyl triselenocarbonate (TSC), were synthesized and used as mediators in radical polymerization. The results indicate that these selenium‐substituted carbonates can control the polymerization of styrene (St) and methyl acrylate, as evidenced by the number‐average molecular weight that increased linearly with the monomer conversion, molecular weights that agreed well with the predicted values, and successful chain extensions. The treatment of the resultant polystyrene by hydrogen peroxide generated polymers with approximately half‐reduced molecular weights, and the absence of carbonate groups and vinyl double bond‐terminated chain ends. The polymerization with these selenium‐substituted carbonates was the same polymerization mechanism as their analogue, the widely used S,S‐dibenzyl trithiocarbonate. This work provided a flexible protocol to incorporate selenium into the polymer chain backbone. Specifically, the treatment of these polymers by oxidation produced “clickable” vinyl‐terminated chain ends, which provided possibilities for further functionalization, for example, via a thiol‐ene click reaction. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2606–2613
• Kinetics and mechanism of the reaction between dibenzyl triselenocarbonate and oxygen-bases
  作者：F.A. Devillanova、G. Verani、L. Henriksen

  DOI：10.1016/0040-4020(80)85061-7

  日期：1980.1

  The base-induced solvolysis of dibenzyl triselenocarbonate in DMSO/water (4:1) has been studied by UV spectrophotometric measurements under pseudo-first order conditions, using KOH, Me4NOH, Bu4nNOH and Bu4nNHCO3 as bases. The reaction is first order with respect to the substrate as well as to the base. Rate constants and activation parameters for the four bases indicate that the rate determining step

  使用KOH，Me 4 NOH，Bu 4 n NOH和Bu 4 n NHCO 3作为碱，通过伪一级反应条件下的紫外分光光度法研究了碱诱导的二硒代三碳酸二苄酯在DMSO /水中的溶剂分解（4：1）。。相对于底物和碱，反应是一级反应。四个碱基的速率常数和激活参数表明速率确定步骤是碱基（作为离子对）在基质上的亲核攻击。由于强烈的亲核性硒酸根类物质，快速反应可能会跟随这一缓慢的步骤。在实验证据的基础上提出了一种试探性的机制。