2,5-dimethyl-3,4-di-iso-propyl-3,4-hexanediol | 54580-24-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 原羧酸衍生物
• 英文名称: 2,5-dimethyl-3,4-di-iso-propyl-3,4-hexanediol
• 英文别名: 3,4-diisopropyl-2,5-dimethyl-hexane-3,4-diol；3,4-Diisopropyl-2,5-dimethyl-hexan-3,4-diol；Tetraisopropyl-aethylenglykol；Isobutyronpinakon；2,5-Dimethyl-3,4-di(propan-2-yl)hexane-3,4-diol
• CAS: 54580-24-4
• 化学式: C₁₄H₃₀O₂
• 分子量: 230.391
• InChiKey: UJIWHPYCRPVKOS-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  249.4±8.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-3,4-di-iso-propyl-3,4-hexanediol 在 copper(II) sulfate 作用下， 生成 octaisopropyl-[1,4]dioxane
  参考文献：
  名称：

  Podocyte Injury Promotes Progressive Nephropathy in Zucker Diabetic Fatty Rats

  摘要：

  The zucker diabetic fatty (ZDF-fa/fa) rat is one of the attractive models for type II diabetes based on impaired glucose tolerance caused by the inherited insulin-resistance gene fa. Characterization of nephropathy in this model may provide useful insights into the mechanism of the progression of diabetic nephropathy. The present study analyzed the pathophysiology of diabetes and nephropathy, including the process of glomerulosclerosis in this model by biochemical and morphometric analyses. In addition, we conducted studies in podocytes in culture to examine the direct effects of high glucose on podocytes. ZDF-fa/fa rats showed overt diabetes despite hyperinsulinemia as early as 3 months of age. Blood glucose levels increased further with a considerable decrease of insulin levels at 5 months. Glomerular filtration rate (GFR) was significantly elevated until 3 months, but fell to the level seen in lean rats by 7 months. Proteinuria started to rise during the period of increased GFR, and increased further after GFR had fallen to within the normal range. Renal fibronectin, collagen iv, and vascular endothelial growth factor mRNA levels were increased at 7 months. Glomerulosclerosis commenced as early as 5 months of age, and was associated with glomerular hypertrophy and mild mesangial expansion with evidence of accentuated podocyte injury, as revealed by increased expression of desmin. Electron microscopy suggested that degeneration of podocytes and the development of tuft adhesions were responsible for the glomerular sclerosis in this model. In addition, glomeruli from the diabetic rats showed up-regulation of the cyclin kinase inhibitors, p21 and p27. Further studies suggested that the increase in p27 expression was predominantly caused by podocytes, because predominant immunolocalization of p27 in podocytes in diabetic rats and high glucose medium induced cell hypertrophy accompanied by p27 up-regulation in differentiated podocyte cell lines. In conclusion, progressive diabetic nephropathy in ZDF-fa/fa rats is associated with evidence of podocyte injury. High concentrations of ambient glucose induced podocyte hypertrophy and stress in vitro, suggesting that the podocyte is a likely target of the diabetic milieu.

  DOI：

  10.1038/labinvest.3780392
• 作为产物：
  描述：

  2,4-二甲基-3-戊酮 在 乙醚 、 sodium 作用下， 生成 2,5-dimethyl-3,4-di-iso-propyl-3,4-hexanediol
  参考文献：
  名称：

  Nasarow, Doklady Akademii Nauk SSSR, 1934, p. IV 288, 291, 293

  摘要：

  DOI：
• 作为试剂：
  描述：

  [UO2Cl2(THF)2]2 在 2,5-dimethyl-3,4-di-iso-propyl-3,4-hexanediol 作用下， 生成 Uranyl chloride trihydrate
  参考文献：
  名称：

  Uranyl complexes with 1,2-diols and tetrahydrofurfuryl alcohols

  摘要：

  2,3-Dimethyl-2,3-butanediol (pinacol, L-1) reacted with uranyl nitrate and acetate hydrates to give [UO2 (NO3)(2)(L-1)]center dot L-1 (1.L-1) and [UO2(OAc)(2)(L-1)] (2), while 2,5-dimethyl-3,4-di-iso-propyl-3,4-hexanediol (L-2) was found to undergo a pinacol rearrangement into the ketone R3CCOR (R = iPr) in the presence of uranyl complexes. Treatment of [UO2(NO3)(0)(H2O)(2)]center dot 4H(2)O with tetrahydrofurfuryl alcohol (L-3) and alpha,alpha-diter-tiobutyltetrahydrofurfuryl alcohol (L-4) led to the formation of [UO2(NO3)(2)(L-3)]center dot H2O (3 center dot H2O) and [UO2 (NO3)(2)(L-4)] (4). The crystal structures show that the metal coordination is similar in the 1,2-diol and ether-alcohol complexes but, in contrast to 1.L-1, 2 and 3 center dot H2O which form one- or two-dimensional hydrogen bonded assemblages, the structure of 4 is composed of discrete molecules, due to the lack of intermolecular hydrogen bonds. The crystal structure of uncomplexed L-2 is also described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.07.100

文献信息

• Reactions of Aliphatic Ketones R2CO (R=Me, Et,iPr, andtBu) with the MCl4/Li(Hg) System (M=U or Ti): Mechanistic Analogies between the McMurry, Wittig, and Clemmensen Reactions
  作者：Claude Villiers、Michel Ephritikhine

  DOI：10.1002/1521-3765(20010716)7:14<3043::aid-chem3043>3.0.co;2-d

  日期：2001.7.16

  system (M = U, Ti) at 20 degrees C revealed significant differences. For R = Me, the reaction proceeded exclusively (M = U) or preferentially (M = Ti) via a metallopinacol intermediate resulting from dimerization of ketyl radicals. Pinacol was liberated by hydrolysis, and tetramethylethylene was obtained after further reduction at 65 degrees C. For R=iPr, formation of iPr2C=CiPr2 as the only coupling

  酮R2CO（R = Me，Et，iPr，tBu）与MCl4 / Li（Hg）系统（M = U，Ti）在20摄氏度下反应的产物分析显示出显着差异。对于R ＝ Me，反应仅通过（由酮基的二聚化产生的）金属麦草醇中间体进行（M ＝ U）或优选地（M ＝ Ti）进行。通过水解释放出频哪醇，并在65℃进一步还原后获得四甲基乙烯。对于R = iPr，形成iPr2C = CiPr2作为唯一的偶联产物，该烯烃不通过还原松果磺酸铀[U] -OCR2CR2O来生产-[U]（R = iPr）在20摄氏度时，相应的松果酸钛对松碳CC键断裂的不稳定性表明，iPr2CO的还原偶联并未通过酮基的二聚作用进行。2的形成 4-二甲基-2-戊烯有利于酮基的脱氧还原而产生的类胡萝卜素中间体。这些结果表明，对于位阻酮，MCMurry反应可以看作是类似Wittig的烯化反应。对于R ＝ tBu，没有获得偶联产物，并且烷烃tBu2CH2是主要产物。类胡萝卜素物质[M]
• New Insights into the Mechanism of the McMurry Reaction
  作者：Claude Villiers、Michel Ephritikhine

  DOI：10.1002/anie.199723801

  日期：1997.11.14

  Not only pinacolate intermediates appear in McMurry reactions of aliphatic ketones R2CO (R = Me, Et, iPr) with MCl4Li(Hg) (M = Ti, U) [Eq. (1)]. Rather, carbenoid species must also be considered. This conclusion was drawn from an exact analysis of the reaction products as well as control experiments with pinacol derivatives. equation image
• Young; Roberts, Journal of the American Chemical Society, 1944, vol. 66, p. 1445
  作者：Young、Roberts

  DOI：——

  日期：——
• BRUCH M.; JUN YOUNG MOO; LUEDTKE A. E.; SCHNEIDER M.; TIMBERLAKE J. W., J. ORG. CHEM., 51,(1986) N 15, 2969-2973
  作者：BRUCH M.、 JUN YOUNG MOO、 LUEDTKE A. E.、 SCHNEIDER M.、 TIMBERLAKE J. W.

  DOI：——

  日期：——