4-hydroxy-2,4-dimethyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester | 6102-13-2

• 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: 4-hydroxy-2,4-dimethyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester
• 英文别名: 5-hydroxy-3,5-dimethyl-2,4-diethoxycarbonylcyclohexanone；diethyl 2,4-dimethyl-4-hydroxy-6-oxocyclohexane-1,3-dicarboxylate；4-Hydroxy-2,4-dimethyl-6-oxo-cyclohexan-1,3-dicarbonsaeure-diaethylester；opt.inakt. 5-Hydroxy-3,5-dimethyl-1-oxo-cyclohexan-2,4-dicarbonsaeure-diaethylester；3,5-Dimethyl-2,4-dicarbethoxy-5-hydroxy-cyclohexanon；(+/-)-5-Hydroxy-3,5-dimethyl-2,4-bis-aethoxycarbonyl-cyclohexanon；diethyl 4-hydroxy-2,4-dimethyl-6-oxocyclohexane-1,3-dicarboxylate
• CAS: 6102-13-2
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: OCWRIZLQAKGMPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2,4-dimethyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester 在 镍 氨 、 氢气 作用下， 以 乙醇 为溶剂， 以60%的产率得到4-amino-6-hydroxy-2,6-dimethyl-cyclohex-3-ene-1,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Kharchenko, V. G.; Smirnova, N. S.; Rybina, G. I., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 12.1, p. 2286 - 2289

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6-dihydroxy-2,6-dimethyl-cyclohex-3-ene-1,3-dicarboxylic acid diethyl ester 生成 4-hydroxy-2,4-dimethyl-6-oxo-cyclohexane-1,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Rabe; Billmann, Justus Liebigs Annalen der Chemie, 1904, vol. 332, p. 31

  摘要：

  DOI：

文献信息

• Synthesis of highly functionalized 3,4-cyclohexane-annelated coumarins
  作者：Chao-Yue Chen、Xiao-Mei Zhang、Jian-Jun Shi、Jie He

  DOI：10.1007/s11164-013-1212-2

  日期：2015.2

  Efficient synthetic access to highly functionalized 3,4-cyclohexane-annelated coumarins has been achieved by combining two methods. First, the important intermediates multisubstituted cyclic β-keto esters were prepared conveniently by condensing a variety of benzaldehydes with ethyl acetoacetate. A series of highly functionalized 3,4-cyclohexane-annelated coumarins were then synthesized by Amberlyst-15-catalyzed

  通过结合两种方法，可以有效地合成高度官能化的3,4-环己烷退火香豆素。首先，通过将各种苯甲醛与乙酰乙酸乙酯缩合，可方便地制备重要的中间体多取代的环状β-酮酯。然后，通过Amberlyst-15催化的多取代环β-酮酯与酚的Pechmann缩合反应，合成了一系列高度官能化的3,4-环己烷-退火香豆素。该合成方法的优点是反应条件温和，对各种官能团的耐受性好，产率令人满意。
• Emelina, E. E.; Gindin, V. A.; Ershov, B. A., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 2263 - 2268
  作者：Emelina, E. E.、Gindin, V. A.、Ershov, B. A.

  DOI：——

  日期：——
• Rabe; Elze, Justus Liebigs Annalen der Chemie, 1902, vol. 323, p. 94
  作者：Rabe、Elze

  DOI：——

  日期：——
• Synthesis of 6H-Dibenzo[b,d]pyran-6-one Derivatives via Coumarin-Fused Cyclohexa-1,3-diene Intermediates
  作者：Zhi-Zhen Huang、Chao-Yue Chen、Yong-Sheng Zhao、Chang-Bing Xiang

  DOI：10.1055/s-0031-1289810

  日期：2012.8

  In the presence of trifluoroacetic acid and methanesulfonic acid (MSA), a series of monohydric and polyhydric phenols readily undergo a domino Pechmann-dehydration reaction with various 4-hydroxy-6-oxocyclohexane-1,3-dicarboxylates to give 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones. Subsequent dehydrogenation of the 7,8-dihydro-6H-dibenzo[b,d]pyran-6-ones was performed expediently with DBU/BrCCl3 to give various 6H-dibenzo[b,d]pyran-6-one derivatives. This strategy has the advantages of inexpensive and easily available raw materials, metal-free procedure, mild reaction conditions, good compatibility with various functional groups, and satisfactory yields.
• Merling, Chemische Berichte, 1905, vol. 38, p. 981
  作者：Merling

  DOI：——

  日期：——