4-chloro-2,6-bis[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbamoylpyridine | 491024-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-2,6-bis[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbamoylpyridine
• 英文别名: 4-chloro-2-N,6-N-bis[2-[(4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]pyridine-2,6-dicarboxamide
• CAS: 491024-68-1
• 化学式: C₂₇H₂₄ClN₅O₄
• 分子量: 517.972
• InChiKey: FGZAWPZCYYSRFN-HOTGVXAUSA-N

物化性质

• 沸点：
  620.3±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苄硫醇 、 4-chloro-2,6-bis[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbamoylpyridine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以72%的产率得到4-thiobenzyl-21,6-bis[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbamoylpyridine
  参考文献：
  名称：

  Dynamic Helical Chirality of an Intramolecularly Hydrogen-Bonded Bisoxazoline

  摘要：

  The synthesis and conformational properties of 2,6-bis-[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbam oylpyridines, 2, have been described. Bisoxazoline 2a was prepared in five steps from 2-nitrobenzoyl chloride in an overall yield of 71%. In contrast to related structures such as 1, bisoxazoline 2a exhibits a highly biased P-type helical conformation in solution and in the solid state. In the crystal lattice, 2a further assembles into a left-handed helical superstructure aligned along the crystallographic c axis. The barrier to helical interconversion, as measured by line-shape analysis of the temperature-dependent H-1 NMR spectra of thiobenzyl derivative 2b, was determined to be quite low (DeltaG(double dagger) = 12.3 kcal/mol), indicating the presence of a highly dynamic helical chirality.

  DOI：

  10.1021/jo026496f
• 作为产物：
  描述：

  邻硝基苯甲酸 在 palladium on activated charcoal 吡啶 、 氯化亚砜 、 草酰氯 、 4 A molecular sieve 、 氢气 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 29.5h， 生成 4-chloro-2,6-bis[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbamoylpyridine
  参考文献：
  名称：

  Dynamic Helical Chirality of an Intramolecularly Hydrogen-Bonded Bisoxazoline

  摘要：

  The synthesis and conformational properties of 2,6-bis-[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbam oylpyridines, 2, have been described. Bisoxazoline 2a was prepared in five steps from 2-nitrobenzoyl chloride in an overall yield of 71%. In contrast to related structures such as 1, bisoxazoline 2a exhibits a highly biased P-type helical conformation in solution and in the solid state. In the crystal lattice, 2a further assembles into a left-handed helical superstructure aligned along the crystallographic c axis. The barrier to helical interconversion, as measured by line-shape analysis of the temperature-dependent H-1 NMR spectra of thiobenzyl derivative 2b, was determined to be quite low (DeltaG(double dagger) = 12.3 kcal/mol), indicating the presence of a highly dynamic helical chirality.

  DOI：

  10.1021/jo026496f

文献信息

• Structural Impact of Coordinating a Helical 2,6-Pyridyl Diamide with Divalent Metals
  作者：Adam J. Preston、Judith C. Gallucci、Jon R. Parquette

  DOI：10.1021/ol062086s

  日期：2006.11.9

  The structural consequences of coordinating 2,6-bis[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbamoylpyridines, 2, with divalent metals such as Cu(II), Ni(II), and Zn(II) are reported. Metal coordination occurs under mild conditions in a manner that preserves the helical bias of the parent ligand in the solid state and in solution. H-1 NMR line-shape analysis indicates that metal coordination increases the helical interconversion barrier, thus rigidifying the dynamic helicity of 2.