1-tert-butyl-1,2-octanedione | 136201-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-tert-butyl-1,2-octanedione
• 英文别名: 3,4-Decanedione, 2,2-dimethyl-；2,2-dimethyldecane-3,4-dione
• CAS: 136201-73-5
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: URRUIURDAWKKSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(Benzotriazol-1-yl)-2,2-dimethyl-4-phenoxydecan-3-one 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 13.5h， 以83%的产率得到1-tert-butyl-1,2-octanedione
  参考文献：
  名称：

  Novel and Facile Syntheses of Alkenyl, Alkynyl, and Aryl 1,2-Diketones

  摘要：

  Novel and facile routes to alkenyl, alkynyl, and aryl 1,2-diketones utilize treatment of benzotriazole derivatives 1, 7a,b, and 15a-d with butyllithium and subsequent reaction with esters or acid chlorides to yield the substituted intermediates 2a-d, 8a,b, and 16a-g. Reactions of the deprotonated 1 and 7 with alpha,beta-unsaturated aldehydes followed by oxidation also produces similar intermediates 5 and 11a,b. Subsequent hydrolyses of the intermediates of type 2, 5, 8, 11, and 16 afford diverse 1,2-diketones in good yields.

  DOI：

  10.1021/jo970092j

文献信息

• Synthesis of .alpha.-diketones by direct, low-temperature, in situ nucleophilic acylation of esters by acyllithium reagents
  作者：Dietmar Seyferth、Robert M. Weinstein、Richard C. Hui、Wei Liang Wang、Colin M. Archer

  DOI：10.1021/jo00020a014

  日期：1991.9

  Addition of n-, sec-, or tert-butyllithium to a CO-saturated solution of an ester, R'CO2R'' in a solvent system of 4:4:1 (by volume) THF/Et2O/pentane at -110-degrees-C (or at -135-degrees-C in 3:1 (by volume) Me2O/THF), followed by hydrolysis with saturated aqueous NH4Cl, results in the formation of alpha-diketones, BuC(O)C(O)R', yellow liquids, in good yield. Similar reactions with diethyl succinate gave in one instance both t-BuC(O)C(O)CH2CH2CO2Et and t-BuC(O)C(O)CH2CH2C(O)C(O)Bu-t. The monoacylation product of dimethyl oxalate, t-BuC(O)C(O)CO2Me, readily formed a crystalline hydrate, t-BuC(O)C(OH)2CO2Me.
• Novel and Facile Syntheses of Alkenyl, Alkynyl, and Aryl 1,2-Diketones
  作者：Alan R. Katritzky、Zuoquan Wang、Hengyuan Lang、Daming Feng

  DOI：10.1021/jo970092j

  日期：1997.6.13

  Novel and facile routes to alkenyl, alkynyl, and aryl 1,2-diketones utilize treatment of benzotriazole derivatives 1, 7a,b, and 15a-d with butyllithium and subsequent reaction with esters or acid chlorides to yield the substituted intermediates 2a-d, 8a,b, and 16a-g. Reactions of the deprotonated 1 and 7 with alpha,beta-unsaturated aldehydes followed by oxidation also produces similar intermediates 5 and 11a,b. Subsequent hydrolyses of the intermediates of type 2, 5, 8, 11, and 16 afford diverse 1,2-diketones in good yields.