2-hydroxy-2-(hydroxymethyl)cyclohexanone | 1004-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-2-(hydroxymethyl)cyclohexanone
• 英文别名: 2-Hydroxy-2-(hydroxymethyl)cyclohexan-1-one
• CAS: 1004-52-0
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: UQURATNDEJJNEO-UHFFFAOYSA-N

物化性质

• 沸点：
  301.8±27.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-(hydroxymethyl)cyclohexanone 在 氢气 作用下， 生成 1-(hydroxymethyl)cyclohexane-1,2-diol
  参考文献：
  名称：

  Colonge,J.; Vaginay,Y., Bulletin de la Societe Chimique de France, 1965, p. 3140 - 3149

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(hydroxymethyl)cyclohexane-1,2-diol 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.33h， 生成 2-hydroxy-2-(hydroxymethyl)cyclohexanone
  参考文献：
  名称：

  Asymmetric synthesis of tanshindiol A.

  摘要：

  The ultrasound-promoted Diels-Alder reaction of 3-methyl-4,5-benzofurandione (10) with appropriately substituted vinylcyclohexenes has led to the synthesis of tanshindiol A (9), a minor component of the Chinese traditional medicine, Dan Shen, prepared from the roots of Salvia miltiorrhiza Bunge. The regioselectivity of the cycloaddition was enhanced by the ultrasonication and was also strongly influenced by the solvent. The asymmetric synthesis of (+)-(4R)-tanshindiol A [(+)-(4R)-91, the naturally occurring enantiomer, proceeded from the optically enriched methyl 6-(benzoyloxy)-1-vinylcyclohexene-6-carboxylate [(-)-(R)-15] or 6-hydroxy-6-(hydroxymethyl)-l-vinylcyclohexene acetonide [(+)-(R)-291 (both 92% ee). Enantioselectivity in the preparation of these diene systems was accomplished by the benzoyl peroxide quench of the lithioenamine derived from methyl 1-oxocyclohexane-2-carboxylate and (S)-valine tert-butyl ester. This procedure, adapted from Koga's asymmetric alkylation of alpha-alkyl beta-keto esters, proved highly effective in preparing the necessary tertiary alcohol in protected form and with high optical purity.

  DOI：

  10.1021/jo00046a009

文献信息

• Colonge,J.; Vaginay,Y., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1965, vol. 260, p. 203 - 205
  作者：Colonge,J.、Vaginay,Y.

  DOI：——

  日期：——
• Fragmentation of Bicyclic γ-Silyloxy-β-hydroxy-α-diazolactones as an Approach to Ynolides
  作者：Ali Bayir、Matthias Brewer

  DOI：10.1021/jo500634d

  日期：2014.7.3

  Medium-sized ynolides were prepared by the Lewis acid-mediated fragmentation of bicyclic gamma-silyloxy-beta-hydroxy-alpha-diazolactones in which the C beta-C gamma bond is the ring fusion bond. Although these lactone fragmentation substrates reacted somewhat less efficiently than their carbocyclic counterparts, the fragmentation provided 11-membered ynolides in up to 84% yield. Unlike prior fragmentations of similar substrates, elevated temperatures were required to obtain optimum yields of the ynolide products. The ynolides reported herein have ring sizes of 10 or 11, which are the smallest reported to date.
• Synthesis of 3-hydroxy-3-(hydroxymethyl)-5-methylcyclohexane-1,2-dione dibenzoate, a reported hydrolytic degradation product of leucogenenol
  作者：D. John Aberhart、Jon Clardy、Pallab K. Ghoshal、He Cunheng、Qitai Zheng

  DOI：10.1021/jo00187a026

  日期：1984.6