2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-yl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-yl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine
• 英文别名: 2-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]-6-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-yl]pyridine
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: TYJXDVNHURCLAX-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-yl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine 以 氯仿 为溶剂， 以79%的产率得到ReCl(CO)3[2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-yl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine]
  参考文献：
  名称：

  Tricarbonylrhenium(I) halide complexes of chiral non-racemic 2-(dioxolanyl)-6-(dioxanyl)pyridine ligands: synthesis, NMR and DFT calculations

  摘要：

  The chiral non-racemic O/N/O donor ligands 2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-yl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine and 2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-deuteryl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine were prepared in a stepwise fashion form 2,6-dibromopyridine. Reaction with the pentacarbonylhalogenorhenium(I) compounds yields the complexes [ReX(CO)(3)L], in which the ligands act in a N/O bidentate chelate fashion. There are eight possible diastereoisomers, three of which are observable in solution. DFT calculations indicate that the relative stability of the diastereoisomers is SR5 > RR5 > SS5 approximate to RS5 > RS6 > SS6 > RR6 > SR6. Above ambient temperature, a dynamic process leads to the exchange of 2 of the 3 diastereoisomers: the free energy of activation is ca. 79 kJ mol(-1). The results of the DFT calculations and the magnitude of DeltaG(+) suggest the dynamic process to be the flip of the co-ordinated acetal ring. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2003.08.012

文献信息

• Tricarbonylrhenium(I) halide complexes of chiral non-racemic 2-(dioxolanyl)-6-(dioxanyl)pyridine ligands: synthesis, NMR and DFT calculations
  作者：Peter J Heard、Paul M King、Phunrawie Sroisuwan、Nikolas Kaltsoyannis

  DOI：10.1016/j.poly.2003.08.012

  日期：2003.11

  The chiral non-racemic O/N/O donor ligands 2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-yl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine and 2-[(4R,5R)-4,5-dimethyl-1,3-dioxolan-2-deuteryl]-6-[(4R,6R)-4,6-dimethyl-1,3-dioxan-2-yl]pyridine were prepared in a stepwise fashion form 2,6-dibromopyridine. Reaction with the pentacarbonylhalogenorhenium(I) compounds yields the complexes [ReX(CO)(3)L], in which the ligands act in a N/O bidentate chelate fashion. There are eight possible diastereoisomers, three of which are observable in solution. DFT calculations indicate that the relative stability of the diastereoisomers is SR5 > RR5 > SS5 approximate to RS5 > RS6 > SS6 > RR6 > SR6. Above ambient temperature, a dynamic process leads to the exchange of 2 of the 3 diastereoisomers: the free energy of activation is ca. 79 kJ mol(-1). The results of the DFT calculations and the magnitude of DeltaG(+) suggest the dynamic process to be the flip of the co-ordinated acetal ring. (C) 2003 Elsevier Ltd. All rights reserved.