methyl 5-hydroxy-2-oxo-cyclohexan-1-carboxylate | 113093-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-hydroxy-2-oxo-cyclohexan-1-carboxylate
• 英文别名: Methyl 5-hydroxy-2-oxocyclohexane-1-carboxylate；methyl 5-hydroxy-2-oxocyclohexane-1-carboxylate
• CAS: 113093-40-6
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: HQWXWNYESIUABE-UHFFFAOYSA-N

物化性质

• 沸点：
  292.1±40.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-2-oxo-cyclohexan-1-carboxylate 在 吡啶 、 咪唑 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 1-(4'-methoxy-phenyl)-5-triisopropylsilyloxy-2-oxo-cyclohexan-1-carboxylate
  参考文献：
  名称：

  Carbanion Stabilization by Distal Silyloxy Groups. Origin of the High Diastereoselectivity in the Formation of Quaternary Centers with Aryllead(IV) Triacetate Reagents

  摘要：

  [GRAPHICS]Derivatives of methyl 5-hydroxy-2-oxo-1-cyclohexanecarboxylate react with aryllead(IV) reagents in high yield and with wide variation in diastereoselectivity. Ab initio calculations are consistent with a heretofore unrecognized attraction between the carbanionic center of the beta-ketoester intermediate and the distal OSiR3 group. This attractive interaction stabilizes the silyl group in the axial conformation and leads to the excellent trans diastereoselection in the formation of quaternary centers.

  DOI：

  10.1021/ol026863+
• 作为产物：
  描述：

  Methyl 5-[tert-butyl(dimethyl)silyl]oxy-2-oxocyclohexane-1-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到methyl 5-hydroxy-2-oxo-cyclohexan-1-carboxylate
  参考文献：
  名称：

  Carbanion Stabilization by Distal Silyloxy Groups. Origin of the High Diastereoselectivity in the Formation of Quaternary Centers with Aryllead(IV) Triacetate Reagents

  摘要：

  [GRAPHICS]Derivatives of methyl 5-hydroxy-2-oxo-1-cyclohexanecarboxylate react with aryllead(IV) reagents in high yield and with wide variation in diastereoselectivity. Ab initio calculations are consistent with a heretofore unrecognized attraction between the carbanionic center of the beta-ketoester intermediate and the distal OSiR3 group. This attractive interaction stabilizes the silyl group in the axial conformation and leads to the excellent trans diastereoselection in the formation of quaternary centers.

  DOI：

  10.1021/ol026863+

文献信息

• Anthranilic acid replacements in a niacin receptor agonist
  作者：Darby Schmidt、Abigail Smenton、Subharekha Raghavan、Hong Shen、Fa-Xiang Ding、Ester Carballo-Jane、Silvi Luell、Tanya Ciecko、Tom G. Holt、Michael Wolff、Andrew Taggart、Larissa Wilsie、Mihajlo Krsmanovic、Ning Ren、Daniel Blom、Kang Cheng、Peggy E. McCann、M.Gerard Waters、James Tata、Steven Colletti

  DOI：10.1016/j.bmcl.2010.04.001

  日期：2010.6

  Niacin is an effective drug for raising HDL cholesterol. However, niacin must be taken in large doses and significant side effects are often observed, including facial flushing, loss of glucose tolerance, and liver toxicity. An anthranilic acid was identified as an agonist of the niacin receptor. In order to improve efficacy and provide structural diversity, replacements for the anthranilic acid were investigated and several compounds with improved properties were identified. (C) 2010 Elsevier Ltd. All rights reserved.
• High-pressure Diels-Alder Reactions of 2-Methylthio- and 2-Acetoxyfuran. An Efficient Entry to 4-hydroxycyclohexanones
  作者：Hiyoshizo Kotsuki、Yuichiro Mori、Tatsuya Ohtsuka、Hitoshi Nishizawa、Masamitsu Ochi、Kiyoshi Matsuoka

  DOI：10.3987/r-1987-09-2347

  日期：——
• Carbanion Stabilization by Distal Silyloxy Groups. Origin of the High Diastereoselectivity in the Formation of Quaternary Centers with Aryllead(IV) Triacetate Reagents
  作者：Joseph P. Konopelski、Jinzhen Lin、Philip J. Wenzel、Hongbo Deng、Gregory I. Elliott、Brian S. Gerstenberger

  DOI：10.1021/ol026863+

  日期：2002.11.1

  [GRAPHICS]Derivatives of methyl 5-hydroxy-2-oxo-1-cyclohexanecarboxylate react with aryllead(IV) reagents in high yield and with wide variation in diastereoselectivity. Ab initio calculations are consistent with a heretofore unrecognized attraction between the carbanionic center of the beta-ketoester intermediate and the distal OSiR3 group. This attractive interaction stabilizes the silyl group in the axial conformation and leads to the excellent trans diastereoselection in the formation of quaternary centers.