(2R,3R)-methyl 2,2,2-trifluoroethyl tartrate | 139015-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,3R)-methyl 2,2,2-trifluoroethyl tartrate
• CAS: 139015-89-7
• 化学式: C₇H₉F₃O₆
• 分子量: 246.14
• InChiKey: QIJAKEKVKLUJBG-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.01
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (4R,5R)-4-(methoxycarbonyl)-5-<(2,2,2-trifluoroethoxy)carbonyl>-2-phenyl-1,3-dioxolane 在 palladium on activated charcoal 氢气 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 以97%的产率得到(2R,3R)-methyl 2,2,2-trifluoroethyl tartrate
  参考文献：
  名称：

  Solid-state and solution conformational analysis of tartrate-derived 1,3-dioxolanes and 1,3,2-dioxaborolanes

  摘要：

  Solid-state (X-ray) and solution conformational analyses of tartrate ester derived 1,3-dioxolanes and 1,3,2-dioxaborolanes are described. The solid-state conformation of dimethyl benzylidenetartrate (5) was found to be one in which the two carbomethoxy groups are pseudoaxial and the ester carbonyls eclipse the adjacent dioxolane C-O bonds. This parallels exactly the conformation previously proposed for the 1,3,2-dioxaborolane unit in the transition state of the reactions of tartrate ester modified allylboronates 1-3 and aldehydes. A correlation was developed between the solution and solid-state conformations of 1,3-dioxolanes 5-7 based on the observed J4,5 coupling constants and the H-4-C-C-H-5 dihedral angle obtained from the X-ray crystal structures. A high resolution variable-temperature H-1 NMR study of 1,3-dioxolane 5 in THF-d8 revealed that J4,5 decreased from 3.72 Hz at 23-degrees-C to 2.91 Hz at -80-degrees-C, providing evidence that the diaxial conformation is increasingly favored as the temperature is decreased. A high resolution variable-temperature H-1 NMR study of ortho ester 12, prepared from dimethyl tartrate and trimethyl orthoacetate, in THF-d8 similarly revealed J4,5 = 5.25 Hz at 23-degrees-C and J4,5 = 4.60 Hz at -80-degrees-C. An analogous solution conformation analysis was also performed with 1,3,2-dioxaborolane derivatives 16 and 17 prepared from methyl trifluoroethyl tartrate (15). Variable-temperature H-1 NMR analysis of 17 in toluene-d8 revealed that J4,5 decreased to a value of J4,5 = 5.0 Hz at 23-degrees-C to J4,5 = 4.3 Hz at -60-degrees-C. The significance of these data to the mechanism of asymmetric induction in the reactions of the tartrate ester modified allylboronates 1-3 and aldehydes is discussed.

  DOI：

  10.1021/jo00033a027