2-(4,4-dimethoxybutyl)cyclopentan-1-one | 187971-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4,4-dimethoxybutyl)cyclopentan-1-one
• CAS: 187971-79-5
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: LBHDGSSOWLPAPO-UHFFFAOYSA-N

物化性质

• 沸点：
  265.2±10.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4,4-dimethoxybutyl)cyclopentan-1-one 在 草酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 2-{[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-(4E)-4-pentenyl}cyclopentanone
  参考文献：
  名称：

  通过不对称分子内迈克尔-羟醛反应容易和立体选择性地进入非外消旋的三环环丁烷：热力学平衡和碘鎓离子的活化。

  摘要：

  连接到环烷酮的（-）-苯基薄荷基烯酸酯的分子内迈克尔-醛醇缩合反应提供了高度非对映化学控制的三环环丁烷。动力学和热力学研究表明，在六甲基二硅氮烷存在下于环境温度下使用三甲基甲硅烷基碘化物的条件下，Michael-aldol反应是可逆的。当该环化过程在动力学和热力学条件下进行时，观察到不同水平的非对映选择性。最后，已经注意到添加碘鎓供体对反应速率的影响。

  DOI：

  10.1021/jo010207q
• 作为产物：
  描述：

  1-phenyl-1H-pyrazol-3-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以97%的产率得到2-(4,4-dimethoxybutyl)cyclopentan-1-one
  参考文献：
  名称：

  Unexpected Prins cyclization: iron-promoted cyclization/hydration of alkynyl-dimethyl acetals

  摘要：

  Unexpected products containing acyl-substituted unsaturated seven-membered carbocycle were synthesized by FeCl(3)-promoted intramolecular Prins cyclization of alkynyl-dimethylacetals in good yields. It is remarkable that the synthesized 7-exocyclic vinyl cations generated as a result of Prins-type cyclization were trapped by H(2)O (no halogen ion) in CH(2)Cl(2) to give the corresponding enol derivatives. Those enol derivatives underwent enol-keto tautomerism and then eliminated one molecule of MeOH to give the corresponding acyl-substituted unsaturated seven-membered carbocycle. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.035

文献信息

• Facile construction of spirobicyclic skeletons by intramolecular aldol reaction: simple formal syntheses of (±)-spirojatamol and (±)-erythrodiene
  作者：Yuji Tokunaga、Maki Yagihashi、Masataka Ihara、Keiichiro Fukumoto

  DOI：10.1039/a606151f

  日期：——

  An intramolecular aldol reaction of keto acetals 1, regioselectively performed with Me3SiI–(Me3Si)2NH leading to spirobicyclic compounds 2 and 3, has been applied to the syntheses of (±)-spirojatamol and (±)-erythrodiene.

  酮缩醛 1 与 Me3SiI-(Me3Si)2NH发生区域选择性分子内醛醇反应，生成螺双环化合物 2 和 3，该反应已应用于 (±)-spirojatamol 和 (±)-erythrodiene 的合成。
• Unexpected Prins cyclization: iron-promoted cyclization/hydration of alkynyl-dimethyl acetals
  作者：Deping Zheng、Wanchun Gong、Zuodong Ma、Bingzhen Ma、Xiaolong Zhao、Zhixiang Xie、Ying Li

  DOI：10.1016/j.tetlet.2010.11.035

  日期：2011.1

  Unexpected products containing acyl-substituted unsaturated seven-membered carbocycle were synthesized by FeCl(3)-promoted intramolecular Prins cyclization of alkynyl-dimethylacetals in good yields. It is remarkable that the synthesized 7-exocyclic vinyl cations generated as a result of Prins-type cyclization were trapped by H(2)O (no halogen ion) in CH(2)Cl(2) to give the corresponding enol derivatives. Those enol derivatives underwent enol-keto tautomerism and then eliminated one molecule of MeOH to give the corresponding acyl-substituted unsaturated seven-membered carbocycle. (C) 2010 Elsevier Ltd. All rights reserved.
• Facile and Stereoselective Access to Nonracemic Tricyclic Cyclobutanes by Asymmetric Intramolecular Michael−Aldol Reaction:  Thermodynamic Equilibrium and Activation by Iodonium Ion
  作者：Kiyosei Takasu、Megumi Ueno、Masataka Ihara

  DOI：10.1021/jo010207q

  日期：2001.6.1

  Intramolecular Michael-aldol reactions of (-)-phenylmenthyl enoates tethered to cycloalkanone affords tricyclic cyclobutanes with high degrees of diastereochemical control. Kinetic and thermodynamic studies revealed that the Michael-aldol reaction is reversible under conditions in which trimethylsilyl iodide is used in the presence of hexamethyldisilazane at ambient temperature. Different levels of

  连接到环烷酮的（-）-苯基薄荷基烯酸酯的分子内迈克尔-醛醇缩合反应提供了高度非对映化学控制的三环环丁烷。动力学和热力学研究表明，在六甲基二硅氮烷存在下于环境温度下使用三甲基甲硅烷基碘化物的条件下，Michael-aldol反应是可逆的。当该环化过程在动力学和热力学条件下进行时，观察到不同水平的非对映选择性。最后，已经注意到添加碘鎓供体对反应速率的影响。