5,5-Dimethyl-1,3-bis[(2,4,6-trimethylphenyl)methyl]-1,3-diazinane-2-thione | 1295637-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5,5-Dimethyl-1,3-bis[(2,4,6-trimethylphenyl)methyl]-1,3-diazinane-2-thione
• 英文别名: 5,5-dimethyl-1,3-bis[(2,4,6-trimethylphenyl)methyl]-1,3-diazinane-2-thione
• CAS: 1295637-09-0
• 化学式: C₂₆H₃₆N₂S
• 分子量: 408.651
• InChiKey: NYISQVGSMGKBRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二甲基丙二胺 在 sodium tetrahydroborate 、 氟硼酸钠 、 甲酸 、 双(三甲基硅烷基)氨基钾 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 100.0h， 生成 5,5-Dimethyl-1,3-bis[(2,4,6-trimethylphenyl)methyl]-1,3-diazinane-2-thione
  参考文献：
  名称：

  Influence of CH3 substituents on tetrahydropyrimidin-2-ylidene: σ-donating properties and in situ catalytic activities of precursor salts/Pd(OAc)2 system for C–C coupling reactions

  摘要：

  In this study, symmetrical and non-symmetrical 1,3-dialkyltetrahydropyrimidinium salts (1 center dot HCl and 2 center dot HBr, respectively), bearing two methyl groups at C-5 position of the pyrimidine ring were synthesized and characterized. One of the new salts 1,3-bis(2,4,6-trimethylbenzyl)-5,5-dimethyl-3,4,5,6-tetrahydropyrimidinium tetrafluoroborate (1a center dot HBF4, 1a = 6-Bn*-Me-2) was converted to cis-[RhCl(6-Bn*-Me-2)(CO)(2)] to determine the sigma-donating properties in comparison to those of their 5-membered NHC complexes. Furthermore, the in situ catalytic activities of all salts, in combination with Pd(OAc)(2), were tested for the HeckeMizoraki and SuzukieMiyaura type C-C coupling reactions. In contrast to the expectation, only the substituents on N,N'-atoms were found to play an important role in the catalytic activity. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.12.041

文献信息

• Influence of CH3 substituents on tetrahydropyrimidin-2-ylidene: σ-donating properties and in situ catalytic activities of precursor salts/Pd(OAc)2 system for C–C coupling reactions
  作者：Deniz Mercan、Engin Çetinkaya、Bekir Çetinkaya

  DOI：10.1016/j.jorganchem.2010.12.041

  日期：2011.4

  In this study, symmetrical and non-symmetrical 1,3-dialkyltetrahydropyrimidinium salts (1 center dot HCl and 2 center dot HBr, respectively), bearing two methyl groups at C-5 position of the pyrimidine ring were synthesized and characterized. One of the new salts 1,3-bis(2,4,6-trimethylbenzyl)-5,5-dimethyl-3,4,5,6-tetrahydropyrimidinium tetrafluoroborate (1a center dot HBF4, 1a = 6-Bn*-Me-2) was converted to cis-[RhCl(6-Bn*-Me-2)(CO)(2)] to determine the sigma-donating properties in comparison to those of their 5-membered NHC complexes. Furthermore, the in situ catalytic activities of all salts, in combination with Pd(OAc)(2), were tested for the HeckeMizoraki and SuzukieMiyaura type C-C coupling reactions. In contrast to the expectation, only the substituents on N,N'-atoms were found to play an important role in the catalytic activity. (C) 2011 Elsevier B.V. All rights reserved.