2,2-Dihydroxy-3-oxo-pent-4-enoic acid tert-butyl ester | 147624-92-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2,2-Dihydroxy-3-oxo-pent-4-enoic acid tert-butyl ester
• 英文别名: tert-butyl 2,2-dihydroxy-3-oxopent-4-enoate
• CAS: 147624-92-8
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: ASJLSIFMIKZAJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  276.5±40.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-Dihydroxy-3-oxo-pent-4-enoic acid tert-butyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-carbomethoxy-8a-carbo-tert-butoxy-2,8-dioxoperhydropyrrolo<1,2-a>pyrimidine
  参考文献：
  名称：

  Addition of amino amides to vinyl vicinal tricarbonyls. Formation of tricyclic 3-azadethiacephams

  摘要：

  Amino amides react as trinucleophiles with vinyl vicinal tricarbonyl esters. Reaction of the primary amino group takes place at the beta-position of the alpha,beta-unsaturated ketone along with addition to the central carbonyl group. In a third-stage reaction, the amide residue adds to the iminium ion formed from the intermediate carbinolamine. The resulting product is a bicyclic or tricyclic (acylamino)pyrrolidone carboxylate. A novel tricyclic 3-azadethiacepham of biological interest has been prepared using this reaction.

  DOI：

  10.1021/jo00035a019
• 作为产物：
  描述：

  水合氯醛 、 4-戊烯酸,2,3-二羰基-,1,1-二甲基乙基酯 以 丙酮 为溶剂， 生成 三氯乙醛 、 2,2-Dihydroxy-3-oxo-pent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  A theoretical and experimental investigation of vicinal tricarbonyl systems and their hydrates

  摘要：

  The conformational preferences of the vinyl vicinal tricarbonyl reagent (VTC) and related triketones have been examined in the context of ab initio molecular orbital theory in order to better understand the properties of these reactive polyelectrophiles. The preferred conformation of the VTC methyl ester has been calculated to have the glyoxal unit twisted almost perpendicular to the plane of the ester unit. These results support the recent conclusions of Schreiber and co-workers on the activity of FK-506 and related compounds for inhibition of the rotamase enzyme. The origin of the enhanced reactivity has been examined via an analysis of the charge density distributions of the triketones and the corresponding hydrates. Electrostatic stabilization appears to be the main driving force for the stability of the hydrates. The energy of hydration for VTC has been calculated to be similar to that of activated aldehydes such as fluoral and chloral. Experimental values are also presented for the energy of hydration of chloral and VTC in acetone solution.

  DOI：

  10.1021/jo00062a029