5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2,2-dimethyl-1-pentanol | 446042-74-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2,2-dimethyl-1-pentanol
• 英文别名: 5-(tert-butyl-dimethylsilanyloxy)-2,2-dimethylpentan-1-ol；5-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-pentan-1-ol；5-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethylpentan-1-ol
• CAS: 446042-74-6
• 化学式: C₁₃H₃₀O₂Si
• 分子量: 246.465
• InChiKey: NLKQBYZPHQTJLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2,2-dimethyl-1-pentanol 在 正丁基锂 、 四丁基氟化铵 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 4,4-dimethylhex-5-enal
  参考文献：
  名称：

  Efficient Construction of the Oxatricyclo[6.3.1.0^0,0]dodecane Core of Komaroviquinone Using a Cyclization/Cycloaddition Cascade of a Rhodium Carbenoid Intermediate

  摘要：

  The rhodium(ll)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures.

  DOI：

  10.1021/ol0513589
• 作为产物：
  描述：

  2,2-二甲基戊-4-烯酸乙酯 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2,2-dimethyl-1-pentanol
  参考文献：
  名称：

  Efficient Construction of the Oxatricyclo[6.3.1.0^0,0]dodecane Core of Komaroviquinone Using a Cyclization/Cycloaddition Cascade of a Rhodium Carbenoid Intermediate

  摘要：

  The rhodium(ll)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures.

  DOI：

  10.1021/ol0513589

文献信息

• DIHYDROPYRIMIDIN-2-ONE COMPOUNDS AND MEDICAL USE THEREOF
  申请人：JAPAN TOBACCO INC.

  公开号：US20160194290A1

  公开（公告）日：2016-07-07

  A compound of Formula [I] or a pharmaceutically acceptable salt thereof: wherein each symbol is defined as in the specification.

  化合物的结构式[I]或其药用盐：其中每个符号的定义如规范中所述。
• A Rh(II)-catalyzed cycloaddition approach toward the synthesis of komaroviquinone
  作者：Albert Padwa、Majid J. Chughtai、Jutatip Boonsombat、Paitoon Rashatasakhon

  DOI：10.1016/j.tet.2008.01.129

  日期：2008.5

  Using a rhodium (II)-catalyzed cyclization/cycloaddition sequence as the key reaction step, the icetexane core of komaroviquinone was constructed by an intramolecular dipolar-cycloaddition of a carbonyl ylide dipole across a tethered pi-bond. The ylide was arrived at by cyclization of a rhodium carbenoid intermediate onto a proximal ester group. Efforts toward the preparation of the required precursor for elaboration to the natural product are discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• The difluoromethylenesulfonic acid group as a monoanionic phosphate surrogate for obtaining PTP1B inhibitors
  作者：Carmen Leung、Justyna Grzyb、Jason Lee、Natalie Meyer、Gabriel Hum、Chenguo Jia、Shifeng Liu、Scott D Taylor

  DOI：10.1016/s0968-0896(02)00062-7

  日期：2002.7

  Three peptides, 7-9, bearing sulfono(difluoromethyl)phenylalanine (F(2)Smp,2), a nonhydrolyzable, monoanionic phosphotyrosine mimetic, were prepared and evaluated as PTP1B inhibitors. The most effective inhibitor was the nonapeptide. ELEF(F(2)Smp)MDYE-NH2. (9) which exhibited a K-i of 360 nM. A comparison of F-2-Smp-bearing peptides 7 [DADE(F(2)Smp)LNH2. K-i=3.4 muM] and 8 [EEDE(F(2)Smp)LNH2. K-i=0.74 muM] with their phosphono(difluoromethyl)phenylalanine (F(2)Pmp)-bearing analogues indicated that F(2)Smp is not as effective a pTyr mimetic as F(2)Pmp by 100- to 130-fold. Although F(2)Smp is not as effective as F(2)Pmp, a comparison of peptide 7 with analagous peptides bearing other monoanionic pTyr mimetics recently reported in the literature indicates that F(2)Smp is about 65-fold more effective than any other non-hydrolyzable, monanionic pTyr mimetic reported to date. To further assess the difluoromethylenesulfonic acid (DFMS) group as a monoanionic phosphate mimetic, a series of 24 nonpeptidyl biaryl compounds bearing the DFMS group were prepared using polymer-supported methodologies and screened for PTP 1B inhibition. Several of these compounds were selected for further study and their IC50's compared to their difluoromethylenephosphonic (DFMP) analogues. The differences in IC50's between the DFMS and DFMP non-peptidyl compounds was not as great as with the F(2)Smp- and F(2)Pmp-bearing peptides. Possible reasons for this and its implication to the design of small molecule PTP1B inhibitors is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.