{(4R,5R)-5-[Bis-(3,5-difluoro-phenyl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-bis-(3,5-difluoro-phenyl)-methanol | 144177-92-4

• 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: {(4R,5R)-5-[Bis-(3,5-difluoro-phenyl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-bis-(3,5-difluoro-phenyl)-methanol
• 英文别名: [(4R,5R)-5-[bis(3,5-difluorophenyl)-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-bis(3,5-difluorophenyl)methanol
• CAS: 144177-92-4
• 化学式: C₃₁H₂₂F₈O₄
• 分子量: 610.501
• InChiKey: IVUMZSNDAGNRRD-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1-溴-3,5-二氟苯 、 (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 magnesium 作用下， 生成 {(4R,5R)-5-[Bis-(3,5-difluoro-phenyl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-bis-(3,5-difluoro-phenyl)-methanol
  参考文献：
  名称：

  New crystalline hosts based on tartaric acid. Synthesis, inclusion properties, and x-ray structural characterization of interaction modes with alcohol guests

  摘要：

  A series of host molecules derived from tartaric acid have been synthesized in optically resolved and racemic forms. Apart from two endo hydroxyl functions and four bulky aromatic groups (TADDOL-type = alpha,alpha,alpha',alpha'-tetraphenyl-1,3-dioxolane-4,5-dimethanols), they have specific polar and apolar substituents of different size, in different number, and in different positions laterally attached to the molecular framework as the characteristic features. These hosts form crystalline inclusion compounds with uncharged organic molecules ranging from protic dipolar (alcohols, amines) to apolar compounds (in all 143 different inclusion species). Inclusion formation, host:guest stoichiometric ratios, and interaction modes depend on the structural features of the host, as supported by X-ray crystallographic studies in nine cases involving MeOH, EtOH, and 2-PrOH. The optically resolved host species with Me and F substituents form linear (spiral) host-guest H-bonded chains in compounds containing MeOH guests, circular motifs of H-bonds in crystals consisting of the racemic host species, while in the presence of larger guest alcohols (2-PrOH) a finite noncyclic H-bonded cluster occurs with the chiral constituents. The crystal packings in structures involving the tetrachloro-substituted hosts and MeOH as guest are dominated by specific Cl...Cl nonbonding interactions which create interhost voids sufficiently large to accommodate a cluster of three H-bonded MeOH moieties. The packing structure of inclusion compounds containing fluoro substituted hosts are stabilized by CH(phenyl)...F interactions.

  DOI：

  10.1021/jo00051a029

文献信息

• New crystalline hosts based on tartaric acid. Synthesis, inclusion properties, and x-ray structural characterization of interaction modes with alcohol guests
  作者：Edwin Weber、Norbert Doerpinghaus、Claus Wimmer、Zafra Stein、Helena Krupitsky、Israel Goldberg

  DOI：10.1021/jo00051a029

  日期：1992.12

  A series of host molecules derived from tartaric acid have been synthesized in optically resolved and racemic forms. Apart from two endo hydroxyl functions and four bulky aromatic groups (TADDOL-type = alpha,alpha,alpha',alpha'-tetraphenyl-1,3-dioxolane-4,5-dimethanols), they have specific polar and apolar substituents of different size, in different number, and in different positions laterally attached to the molecular framework as the characteristic features. These hosts form crystalline inclusion compounds with uncharged organic molecules ranging from protic dipolar (alcohols, amines) to apolar compounds (in all 143 different inclusion species). Inclusion formation, host:guest stoichiometric ratios, and interaction modes depend on the structural features of the host, as supported by X-ray crystallographic studies in nine cases involving MeOH, EtOH, and 2-PrOH. The optically resolved host species with Me and F substituents form linear (spiral) host-guest H-bonded chains in compounds containing MeOH guests, circular motifs of H-bonds in crystals consisting of the racemic host species, while in the presence of larger guest alcohols (2-PrOH) a finite noncyclic H-bonded cluster occurs with the chiral constituents. The crystal packings in structures involving the tetrachloro-substituted hosts and MeOH as guest are dominated by specific Cl...Cl nonbonding interactions which create interhost voids sufficiently large to accommodate a cluster of three H-bonded MeOH moieties. The packing structure of inclusion compounds containing fluoro substituted hosts are stabilized by CH(phenyl)...F interactions.