nonane-2,5,8-triol | 1214756-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: nonane-2,5,8-triol
• 英文别名: 2,5,8-nonatriol；Nonane-2,5,8-triol
• CAS: 1214756-76-9
• 化学式: C₉H₂₀O₃
• 分子量: 176.256
• InChiKey: UERNZDHTINMQQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(5-methyl-2-furanyl)-3-buten-2-one 在 acetonitrile(4′-phenyl-2,2′:6′,2”-terpyridine)(8-quinolinethiolate)ruthenium(II) triflate 、 氢气 作用下， 以 水 为溶剂， 200.0 ℃ 、5.5 MPa 条件下， 反应 16.0h， 以29%的产率得到nonane-2,5,8-triol
  参考文献：
  名称：

  Ruthenium-8-quinolinethiolate-phenylterpyridine versus ruthenium-bipyridine-phenyl-terpyridine complexes as homogeneous water and high temperature stable hydrogenation catalysts for biomass-derived substrates

  摘要：

  [(4'-Ph-terpy)(bipy)Ru(L)](OTf)(n) and [(4'-Ph-terpy)(quS)Ru(L)](OTf)(n) (n = 0 or 1 depending on the charge of L, L = labile ligand, e.g., H2O, CH3CN or OTf, bipy = 2,2'-bipyridine, quS = quinoline-8-thiolate) have been evaluated as catalysts for the hydrogenation of the biomass-derivable C6-substrates 2,5-dimethylfuran (obtainable from 5-hydroxymethylfurfural) and 2,5-hexanedione (the hydrolysis product of 2,5-dimethylfuran). Operating in aqueous acidic medium at T = 175-225 degrees C the bipy complex is only marginally active, while the quinoline-8-thiolate complex realizes yields of hydrogenated products up to 97% starting from 2,5-hexanedione and up to 66% starting from 2,5-dimethylfuran. The catalyst can also convert the 5-HMF derived acetone 4-(5-methyl-2-furanyl)-3-buten-2-one into 2,5,8-nonatriol, a potentially valuable cross-linker for polymer formulations. On the basis of DFT calculations, the higher activity of the quinoline-8-thiolate complex is proposed to be rooted in a metal-ligand bifunctional mechanism for the heterolytic activation and transfer of dihydrogen to the carbonyl substrate with the hydride-thiol complex [(4'-Ph-terpy)(quSH)Ru(H)r as the active catalyst. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.10.049

文献信息

• Synthesis of Glycerol Homologues
  作者：Mark Trudell、Kiran Thota

  DOI：10.1055/s-0033-1339185

  日期：——

  A series of monoprotected glycerol homologues and triols were prepared in high overall yields (>90%) via the hydroboration-oxidation of the corresponding dienols. Hydroboration with disiamylborane and concomitant alkaline oxidation (NaOH, H2O2) was found to be a mild, high-yielding, and highly efficient method for the construction of a variety of glycerol homologues.
• Ruthenium-8-quinolinethiolate-phenylterpyridine versus ruthenium-bipyridine-phenyl-terpyridine complexes as homogeneous water and high temperature stable hydrogenation catalysts for biomass-derived substrates
  作者：Ryan J. Sullivan、Jin Kim、Caroline Hoyt、Louis A. (Pete) Silks、Marcel Schlaf

  DOI：10.1016/j.poly.2015.10.049

  日期：2016.3

  [(4'-Ph-terpy)(bipy)Ru(L)](OTf)(n) and [(4'-Ph-terpy)(quS)Ru(L)](OTf)(n) (n = 0 or 1 depending on the charge of L, L = labile ligand, e.g., H2O, CH3CN or OTf, bipy = 2,2'-bipyridine, quS = quinoline-8-thiolate) have been evaluated as catalysts for the hydrogenation of the biomass-derivable C6-substrates 2,5-dimethylfuran (obtainable from 5-hydroxymethylfurfural) and 2,5-hexanedione (the hydrolysis product of 2,5-dimethylfuran). Operating in aqueous acidic medium at T = 175-225 degrees C the bipy complex is only marginally active, while the quinoline-8-thiolate complex realizes yields of hydrogenated products up to 97% starting from 2,5-hexanedione and up to 66% starting from 2,5-dimethylfuran. The catalyst can also convert the 5-HMF derived acetone 4-(5-methyl-2-furanyl)-3-buten-2-one into 2,5,8-nonatriol, a potentially valuable cross-linker for polymer formulations. On the basis of DFT calculations, the higher activity of the quinoline-8-thiolate complex is proposed to be rooted in a metal-ligand bifunctional mechanism for the heterolytic activation and transfer of dihydrogen to the carbonyl substrate with the hydride-thiol complex [(4'-Ph-terpy)(quSH)Ru(H)r as the active catalyst. (C) 2015 Elsevier Ltd. All rights reserved.