(R)-N-[1-(hydroxymethyl)propyl]-2-methylpropanethioamide | 420133-78-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: (R)-N-[1-(hydroxymethyl)propyl]-2-methylpropanethioamide
• 英文别名: N-[(2R)-1-hydroxybutan-2-yl]-2-methylpropanethioamide
• CAS: 420133-78-4
• 化学式: C₈H₁₇NOS
• 分子量: 175.295
• InChiKey: DUECPKDZVXMQMA-SSDOTTSWSA-N

物化性质

• 沸点：
  258.9±42.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-[1-(hydroxymethyl)propyl]-2-methylpropanethioamide 在 叔丁基锂 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 5.17h， 生成 (R)-methyl-2-methyl-2-(4-ethyl-4,5-dihydro-2-thiazolyl)propanedithioate
  参考文献：
  名称：

  Synthesis of new chiral thiazoline-containing ligands

  摘要：

  New chiral ligands. including bi- and tridentate thiazoline derivatives, analogues of known oxazolines, have been synthesized by it general and convenient procedure. starting from dithioesters and commercial enantiopure 2-aminoalcohols. A preliminary Lest shows the ability of such ligands to act as asymmetric catalysts in Pd-catalyzed allylic substitution reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00481-5
• 作为产物：
  描述：

  2-氨基丁醇 、 methyl 2-methylpropanedithioate 在 三乙胺 作用下， 生成 (R)-N-[1-(hydroxymethyl)propyl]-2-methylpropanethioamide
  参考文献：
  名称：

  Synthesis and properties of thiazoline based ionic liquids derived from the chiral pool

  摘要：

  我们以多克为单位制备了一类新型的手性离子液体，它们来自氨基醇。外消旋莫舍尔酸盐的初步实例显示了它们在手性识别方面的潜力。

  DOI：

  10.1039/b308814f

文献信息

• Synthesis and properties of thiazoline based ionic liquids derived from the chiral pool
  作者：Jocelyne Levillain、Guillaume Dubant、Isabelle Abrunhosa、Mihaela Gulea、Annie-Claude Gaumont

  DOI：10.1039/b308814f

  日期：——

  A novel class of chiral ionic liquids derived from amino alcohols is prepared in multi-gram scale. Their potential in chiral recognition is shown in a preliminary example with racemic Mosher's acid salt.

  我们以多克为单位制备了一类新型的手性离子液体，它们来自氨基醇。外消旋莫舍尔酸盐的初步实例显示了它们在手性识别方面的潜力。
• Synthesis of new chiral thiazoline-containing ligands
  作者：Isabelle Abrunhosa、Mihaela Gulea、Jocelyne Levillain、Serge Masson

  DOI：10.1016/s0957-4166(01)00481-5

  日期：2001.11

  New chiral ligands. including bi- and tridentate thiazoline derivatives, analogues of known oxazolines, have been synthesized by it general and convenient procedure. starting from dithioesters and commercial enantiopure 2-aminoalcohols. A preliminary Lest shows the ability of such ligands to act as asymmetric catalysts in Pd-catalyzed allylic substitution reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• (N,N) vs. (N,S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study
  作者：Alexander Betz、Lian Yu、Markus Reiher、Annie-Claude Gaumont、Paul-Alain Jaffrès、Mihaela Gulea

  DOI：10.1016/j.jorganchem.2008.04.044

  日期：2008.7

  New thiazoline-containing ligands including non-symmetric bis(thiazolines) and oxazoline-thiazolines were synthesized and then compared to C-2-symmetric bis(thiazolines) in the palladium-catalyzed allylic substitution. The experimental results obtained in this study support the hypothesis of a competition between the (N,N) and the (N,S) palladium chelation, when sterically hindered bis(thiazolines) are used as ligands. A quantum chemical study performed on the Pd-complexes derived from three selected ligands, two C-2-symmetric bis(thiazolines) and one oxazoline-thiazoline, also supports this hypothesis. (C) 2008 Elsevier B.V. All rights reserved.