1,3,5-triacetamido-1,3,5-trideoxy-cis-inositol | 6988-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,5-triacetamido-1,3,5-trideoxy-cis-inositol
• 英文别名: Tri-N-Acetyl-cis-inosatriamin-(1.3.5)
• CAS: 6988-72-3；18778-11-5
• 化学式: C₁₂H₂₁N₃O₆
• 分子量: 303.315
• InChiKey: FCHHTTXLCXBVET-CJXDBHJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  147.99
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  cobalt(II) nitrate hexahydrate 、 1,3,5-triacetamido-1,3,5-trideoxy-cis-inositol 在 H₂O 作用下， 以 甲醇 为溶剂， 以81%的产率得到bis(1,3,5-triacetamido-1,3,5-trideoxy-cis-inositol)cobalt(II) nitrate octahydrate
  参考文献：
  名称：

  Metal binding of polyalcohols. Part 2. (all-cis-1,3,5-Triaminocyclohexane)cobalt(III), a facially co-ordinating, diamagnetic probe exemplified by its complex formation with cis-inositol

  摘要：

  Interactions of cis-inositol (ino) (cyclohexane-1,2,3,4,5,6-hexol) and 1,3,5-triacetamido-1,3,5-trideoxy-cis-inositol (taino) with the Co(tach)3+ unit (tach = all-cis-1,3,5-triaminocyclohexane) have been examined. Reaction with cis-inositol resulted in the formation of [Co(tach)(H-1ino)]2+, with taino in either [(tach)Co(mu-OH)2(mu-NO,)Co(tach)]3+ or [Co(taino)2]2+. The crystal structures of [Co(tach)(H-1-ino)][NO3]2 1, [(tach)Co(mu-OH)2(mu-NO3)Co(tach)] [NO3]3.0.75H2O 2, [Co(taino)2][NO3]2.4H2O 3a and [Co(taino)2][NO3]2.8H2O 3b have been determined. The Co(III) in solid 1 is bound to two hydroxyl groups and one alkoxo group of cis-inositol in a syn-1,3,5-triaxial arrangement. In aqueous solution, [Co(tach) (ino)]3+ reacted as a strong acid. The values pK1 < 2.0, pK2= 4.05(2) and pK3 = 6.68(2) have been established by potentiometric measurements (0.1 mol dm-3 KNO3, 25-degrees-C). In addition, an isomerization reaction [binding of the Co(tach)3+ unit to three adjacent hydroxyl groups in an axial-equatorial-axial arrangement] as well as the reversible dissociation of cis-inositol have been observed by NMR measurements. Both reactions show a characteristic pH dependence for the equilibrium composition as well as for the reaction rate. The individual microscopic acidity constants of the two isomers were elucidated by H-1 NMR-monitored pD titrations. Molecular mechanics calculations were used to rationalize differences in energy between the two isomeric forms. The rather weak binding of neutral polyalcohols to metal ions was confirmed. However, it was also demonstrated that the deprotonated polyols can act as powerful ligands for metal ions.

  DOI：

  10.1039/dt9940001689

文献信息

• Hegetschweiler, Kaspar; Ghisletta, Michele; Hausherr-Primo, Lorenza, Inorganic Chemistry, 1995, vol. 34, # 7, p. 1950 - 1953
  作者：Hegetschweiler, Kaspar、Ghisletta, Michele、Hausherr-Primo, Lorenza、Kradolfer, Thomas、Schmalle, Helmut W.、Gramlich, Volker

  DOI：——

  日期：——