scyllo-inositol 1,3,5-orthoformate | 98575-48-5

• 英文名称: scyllo-inositol 1,3,5-orthoformate
• 英文别名: scyllo-inositol monoorthoformate；myo-inositol orthoformate
• CAS: 98575-48-5
• 化学式: C₇H₁₀O₆
• 分子量: 190.153
• InChiKey: WJJFNSGWGPSKAO-RYDQGMCCSA-N

物化性质

• 沸点：
  489.7±45.0 °C(Predicted)
• 密度：
  1.836±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.45
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  scyllo-inositol 1,3,5-orthoformate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 41.0h， 生成 (1S,2R,3S,4R,5R,6S)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl (1S,1'S,4R,4'R)-bis(4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate)
  参考文献：
  名称：

  Rapid Synthesis of the Enantiomers ofmyo-Inositol-1,3,4,5-tetrakisphosphate by Direct Chiral Desymmetrization ofmyo-Inositol Orthoformate

  摘要：

  DOI：

  10.1002/anie.199714721
• 作为产物：
  描述：

  (1S,5S,7R,8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]decan-6-one 在 palladium dihydroxide sodium tetrahydroborate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.33h， 生成 scyllo-inositol 1,3,5-orthoformate
  参考文献：
  名称：

  Synthesis of mono- and unsymmetrical bis-orthoesters of scyllo-inositol

  摘要：

  DOI：

  10.1021/jo00222a046
• 作为试剂：
  描述：

  苯丙醛 、 2-环己烯-1-酮 在 三丁基膦 、 scyllo-inositol 1,3,5-orthoformate 作用下， 以 氘代四氢呋喃 为溶剂， 反应 3.5h， 生成 2-(1-hydroxy-3-phenylpropyl)cyclohex-2-enone
  参考文献：
  名称：

  Preorganized Hydrogen Bond Donor Catalysts: Acidities and Reactivities

  摘要：

  Measured DMSO pK(a) values for a series of rigid tricyclic adamantane-like triols containing 0-3 trifluoromethyl groups (i.e., 3(0)-3(3)) are reported. The three compounds with CF3 substituents are similar or more acidic than acetic acid (pK(a) = 13.5 (3(1)), 9.5 (3(2)), 7.3 (3(3)) vs 12.6 (HOAc)), and the resulting hydrogen bond network enables a remote gamma-trifluoromethyl group to enhance the acidity as well as one located at the alpha-position. Catalytic abilities of 3(0) - 3(3) were also examined. In a nonpolar environment a rate enhancement of up to 100-fold over flexible acyclic analogs was observed presumably due to an entropic advantage of the locked-in structure. Gas-phase acidities are found to correlate with the catalytic activity better than DMSO pKa values and appear to be a better measure of acidities in low dielectric constant media. These trends are reduced or reversed in polar solvents highlighting the importance of the reaction environment.

  DOI：

  10.1021/acs.joc.5b01475

文献信息

• Is potential coordination of alkali metal ions to stereodefined polyoxygenated cyclohexanes an adequate driving force for fostering the adoption of axial conformers?
  作者：Leo A. Paquette、Peter R. Selvaraj、Karin M. Keller、Jennifer S. Brodbelt

  DOI：10.1016/j.tet.2004.10.011

  日期：2005.1

  Inositol orthoesters have been developed as precursors to stereodefined hexakis polyoxygenated cyclohexanes. The objective of the study was to determine if all-trans systems could be coaxed by alkali metal ions into adopting the all-axial coordinative features. This high level coordination cannot be matched by epimers whose only option is to experience monocomplexation. Only very low levels of coordination

  已经开发出肌醇原酸酯作为立体定义的六烷基多加氧环己烷的前体。该研究的目的是确定碱金属离子是否可以促使全反式系统采用全轴配位特征。这种高水平的协调能力是差向异构体无法匹敌的，差向异构体的唯一选择是经历单一复杂性。所讨论的配体在溶液中仅表现出非常低的配位水平。基于涉及每个配体和一种或多种金属的竞争实验，电喷雾电离质谱也用于评估肌醇配体的金属络合特性。
• Chiral analogs of enterobactin with hydrophilic or lipophilic properties
  作者：Bruno Tse、Yoshito Kishi

  DOI：10.1021/ja00070a051

  日期：1993.8