S-cubyl-N,N-dimethyldithiocarbamate | 438535-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 二硫代氨基甲酸及其衍生物
• 英文名称: S-cubyl-N,N-dimethyldithiocarbamate
• 英文别名: cuban-1-yl N,N-dimethylcarbamodithioate
• CAS: 438535-20-7
• 化学式: C₁₁H₁₃NS₂
• 分子量: 223.363
• InChiKey: LACOMHSVIMIEQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-cubyl-N,N-dimethyldithiocarbamate 在 吡啶 、 lithium aluminium tetrahydride 、 碘 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 14.0h， 生成 dicubyl disulfide
  参考文献：
  名称：

  Dicubyl Disulfide

  摘要：

  Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C-S bond on record (1.771 A). In contrast to previous generalizations, density functional theory calculations predict a low S-S rotation barrier similar to that for t-BuSSBu-t. Low-temperature (13)C NMR (600 MHz) confirms the prediction.

  DOI：

  10.1021/ja025823y
• 作为产物：
  描述：

  福美双 、 iodocubane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到S-cubyl-N,N-dimethyldithiocarbamate
  参考文献：
  名称：

  Dicubyl Disulfide

  摘要：

  Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C-S bond on record (1.771 A). In contrast to previous generalizations, density functional theory calculations predict a low S-S rotation barrier similar to that for t-BuSSBu-t. Low-temperature (13)C NMR (600 MHz) confirms the prediction.

  DOI：

  10.1021/ja025823y

文献信息

• Dicubyl Disulfide
  作者：Ronny Priefer、Yoon Joo Lee、Fabiola Barrios、Jordan H. Wosnick、Anne-Marie Lebuis、Patrick G. Farrell、David N. Harpp、Aiming Sun、Shaoxiong Wu、James P. Snyder

  DOI：10.1021/ja025823y

  日期：2002.5.1

  Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C-S bond on record (1.771 A). In contrast to previous generalizations, density functional theory calculations predict a low S-S rotation barrier similar to that for t-BuSSBu-t. Low-temperature (13)C NMR (600 MHz) confirms the prediction.