2,4-dimethyl-3-[1]naphthyl-pentan-3-ol | 14056-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,4-dimethyl-3-[1]naphthyl-pentan-3-ol
• 英文别名: 2,4-Dimethyl-3-naphthalen-1-ylpentan-3-ol；2,4-dimethyl-3-naphthalen-1-ylpentan-3-ol
• CAS: 14056-38-3
• 化学式: C₁₇H₂₂O
• 分子量: 242.361
• InChiKey: CVCNORJLEBCYSA-UHFFFAOYSA-N

物化性质

• 沸点：
  141-144 °C(Press: 0.5 Torr)
• 密度：
  1.0698 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-3-[1]naphthyl-pentan-3-ol 在 copper(II) sulfate 作用下， 生成 1-(1-isopropyl-2-methyl-propenyl)-naphthalene
  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：

  naphthalen-1-yl-lithium 、 2,4-二甲基-3-戊酮 以 四氢呋喃 为溶剂， 生成 2,4-dimethyl-3-[1]naphthyl-pentan-3-ol
  参考文献：
  名称：

  动态核磁共振的构象研究。59.（1）受阻萘甲醇的阻转异构体中构象对映异构体的立体动力学。

  摘要：

  萘二烷基甲醇ArRR'COH（Ar = 1-萘基或1-萘基-2-甲基）以一对阻转异构体的形式存在，这些阻转异构体是由围绕Ar-COH键的受限旋转产生的。它们可以通过低温NMR光谱进行检测，但是如果两个烷基取代基均为大的叔丁基，则它们也可以在室温下作为稳定的化合物分离（一个这样的例子由化合物1提供，R = R'= Bu（t ），其中Ar = 1-萘基）。发现这些阻转异构体相互转化的活化自由能（DeltaG（））在7.6 kcal mol（-）（1）之间变化（如7中，R = R'= Me，Ar = 1-萘基-2-甲基）和32.9 kcal mol（-）（1）（与1相同）。通过差值NOE实验或利用在两种阻转异构体中相差很大的H-8化学位移来分配正周平面（sp）或反周平面（ap）结构。取决于取代基，在平衡处更稳定的物质可以是sp或ap阻转异构体。当R = R'= Pr（i）且R = R'= Et（如果Ar

  DOI：

  10.1021/jo970113+

文献信息

• Conformational Studies by Dynamic Nuclear Magnetic Resonance. 59.¹ Stereodynamics of Conformational Enantiomers in the Atropisomers of Hindered Naphthylcarbinols
  作者：Daniele Casarini、Lodovico Lunazzi、Andrea Mazzanti

  DOI：10.1021/jo970113+

  日期：1997.5.1

  Naphthyldialkylmethanols ArRR'COH (Ar = 1-naphthyl or 1-naphthyl-2-methyl) exist as a pair of atropisomers created by the restricted rotation about the Ar-COH bond. They can be detected by low-temperature NMR spectroscopy but can also be separated as stable compounds at room temperature if both the alkyl substituents are bulky tert-butyl groups (one such example is provided by compound 1, R = R' = Bu(t) with Ar = 1-naphthyl)

  萘二烷基甲醇ArRR'COH（Ar = 1-萘基或1-萘基-2-甲基）以一对阻转异构体的形式存在，这些阻转异构体是由围绕Ar-COH键的受限旋转产生的。它们可以通过低温NMR光谱进行检测，但是如果两个烷基取代基均为大的叔丁基，则它们也可以在室温下作为稳定的化合物分离（一个这样的例子由化合物1提供，R = R'= Bu（t ），其中Ar = 1-萘基）。发现这些阻转异构体相互转化的活化自由能（DeltaG（））在7.6 kcal mol（-）（1）之间变化（如7中，R = R'= Me，Ar = 1-萘基-2-甲基）和32.9 kcal mol（-）（1）（与1相同）。通过差值NOE实验或利用在两种阻转异构体中相差很大的H-8化学位移来分配正周平面（sp）或反周平面（ap）结构。取决于取代基，在平衡处更稳定的物质可以是sp或ap阻转异构体。当R = R'= Pr（i）且R = R'= Et（如果Ar
• Conformational Studies by Dynamic NMR. 64.¹ Stereomutations of Atropisomers and of Conformational Enantiomers in Ethers of Hindered Naphthylcarbinols
  作者：Daniele Casarini、Lodovico Lunazzi、Andrea Mazzanti、Elisabetta Foresti

  DOI：10.1021/jo9804801

  日期：1998.7.1

  Methyl or ethyl ethers of 1-naphthyl carbinols ArCR2OR' (Ar = 1-naphthyl, R' = Me, Et) can occur in a range of rotational conformations whose population varies with the nature of the substituents R. The passage between such conformation minima is achieved by rotation, during which one group R or OR' passes either the 2- or the 8-position of the naphthalene, and depending on the nature of R and OR', some of these interconversions are slow on the NMR time scale. Dynamic NMR experiments, supported by molecular mechanics calculations, show that different minima are preferred as the R group changes. These conformations are identified, their populations are determined, and the barriers to their interconversions are measured. In particular when R is a tert-butyl group, two atropisomers (with the OMe moiety near the 2- or 8-position) could be physically separated and their structures determined by NOE experiments in solution and X-ray diffraction in the solid state. Each of these exists as a pair of stereolabile enantiomers, with a barrier of 9-10 kcal mol(-1) for interconversion.
• Podocyte Injury Promotes Progressive Nephropathy in Zucker Diabetic Fatty Rats
  作者：Sachi Hoshi、Yujing Shu、Fusayo Yoshida、Tomoko Inagaki、Jiro Sonoda、Teruo Watanabe、Ken-ichi Nomoto、Michio Nagata

  DOI：10.1038/labinvest.3780392

  日期：2002.1

  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.