(4S)-4-isopropyl-2-(2-methyl-1,3-dithian-2-yl)-4,5-dihydro-1,3-oxazole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (4S)-4-isopropyl-2-(2-methyl-1,3-dithian-2-yl)-4,5-dihydro-1,3-oxazole
• 英文别名: (4S)-2-(2-methyl-1,3-dithian-2-yl)-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• 化学式: C₁₁H₁₉NOS₂
• 分子量: 245.41
• InChiKey: AEBBVIZZAZXHET-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-1,3-二噻烷 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 、 对甲苯磺酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 (4S)-4-isopropyl-2-(2-methyl-1,3-dithian-2-yl)-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis

  摘要：

  A series of new chiral oxazoline-1,3-dithianes has been easily synthesized and used as ligands for asymmetric catalysis. The conjugate addition of Et2Zn to enones resulted in ees of up to 69%, whereas the Pd-catalyzed allylic alkylation led to the expected products in almost quantitative yields and up to 90% enantioselectivity. The ligand's conformation has been explored using a combination of X-ray and NMR measurements, indicating the presence of a remarkable anomeric effect, which accounts for the preference of the oxazoline ring for the axial location. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.043

文献信息

• Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis
  作者：Elena Capitò、Luca Bernardi、Mauro Comes-Franchini、Francesco Fini、Mariafrancesca Fochi、Salvatore Pollicino、Alfredo Ricci

  DOI：10.1016/j.tetasy.2005.08.043

  日期：2005.10

  A series of new chiral oxazoline-1,3-dithianes has been easily synthesized and used as ligands for asymmetric catalysis. The conjugate addition of Et2Zn to enones resulted in ees of up to 69%, whereas the Pd-catalyzed allylic alkylation led to the expected products in almost quantitative yields and up to 90% enantioselectivity. The ligand's conformation has been explored using a combination of X-ray and NMR measurements, indicating the presence of a remarkable anomeric effect, which accounts for the preference of the oxazoline ring for the axial location. (c) 2005 Elsevier Ltd. All rights reserved.