1,1-dimethylethyl 2-ethanoate | 141344-07-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1-dimethylethyl 2-ethanoate
• 英文别名: 1,1-dimethylethyl 2-[N-methyl-N-[4,8-dimethyl-3E,7E-nonadienyl]amino]ethanoate；tert-butyl 2-[[(3E)-4,8-dimethylnona-3,7-dienyl]-methylamino]acetate
• CAS: 141344-07-2
• 化学式: C₁₈H₃₃NO₂
• 分子量: 295.466
• InChiKey: QMXKMOYHAPGORO-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 2-ethanoate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 Methanesulfonic acid 2-[((E)-4,8-dimethyl-nona-3,7-dienyl)-methyl-amino]-ethyl ester
  参考文献：
  名称：

  Inhibition of Geranylgeranyl Diphosphate Synthase by Bisphosphonates and Diphosphates:  A Potential Route to New Bone Antiresorption and Antiparasitic Agents

  摘要：

  We report the inhibition of a human recombinant geranylgeranyl diphosphate synthase (GGPPSase) by 23 bisphosphonates and six azaprenyl diphosphates. The IC50 values range from 140 nM to 690,muM. None of the nitrogen-containing bisphosphonates that inhibit farnesyl diphosphate synthase were effective in inhibiting the GGPPSase enzyme. Using three-dimensional quantitative structure-activity relationship/comparative molecular field analysis (CoMFA) methods, we find a good correlation between experimental and predicted activity: R-2 = 0.938, R-cv(2) = 0.900, R-bs(2) = 0.938, and F-test = 86.8. To test the predictive utility of the CoMFA approach, we used three training sets of 25 compounds each to generate models to predict three test sets of three compounds. The rms pIC(50) error for the nine predictions was 0.39. We also investigated the pharmacophore of these GGPPSase inhibitors using the Catalyst method. The results demonstrated that Catalyst predicted the pIC(50) values for the nine test set compounds with an rms error of 0.28 (R-2 between experimental and predicted activity of 0.948).

  DOI：

  10.1021/jm010412y
• 作为产物：
  描述：

  香叶基氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 1,1-dimethylethyl 2-ethanoate
  参考文献：
  名称：

  Synthesis and characterization of aza analog inhibitors of squalene and geranylgeranyl diphosphate synthases.

  摘要：

  One-carbon homologation of geranyl and farnesyl chlorides to secondary N-methylamines (12 and 17) via alpha-lithioformamidine alkylations followed by N-alkylation with bromoacetate esters afforded alpha-(homogeranylamino)-and alpha-(homofarnesylamino)acetates 13 and 18. After alpha-farnesylation of 13, hydride reductions gave branched and straight-chain tertiary beta-amino alcohols 15 and 19. The diphosphate derivatives (7 and 8) of 15 and 19 prepared by SN2 displacements may be regarded as "aza analogs" of plausible carbocation intermediates (5 and 6) in the biosynthesis of squalene and geranylgeranyl diphosphate since, in preliminary collaborative evaluations, they inhibit the respective synthase enzymes at micromolar concentrations.

  DOI：

  10.1021/jo00038a038