3-oxiranyl-3-hydroxy-2-methyl-2-(2-methyl-2-propenyl)cyclopentan-1-one | 171777-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxiranyl-3-hydroxy-2-methyl-2-(2-methyl-2-propenyl)cyclopentan-1-one
• 英文别名: 3-hydroxy-2-methyl-2-(2-methylprop-2-enyl)-3-(oxiran-2-yl)cyclopentan-1-one
• CAS: 171777-48-3
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: KFRDPDACFCBHGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.83
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-oxiranyl-3-hydroxy-2-methyl-2-(2-methyl-2-propenyl)cyclopentan-1-one 在 溴化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以63%的产率得到(1S,2R,6R,8R)-2-Hydroxy-6,8-dimethyl-11-oxa-tricyclo[6.2.1.0^2,6]undecan-5-one
  参考文献：
  名称：

  Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols:  Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-Endo-Tet Ring Closures

  摘要：

  The stereocontrolled construction of cycloheptanoid ring systems, relevant to sesquiterpenes and diterpenes of biological activity, is described. A new and highly efficient cyclization methodology provides stereocontrolled routes to polyfunctionalized and hydroxylated cycloheptanoid (and cyclohexanoid) rings. An alkyne or alkene terminus is shown to cyclize onto a 2,3-epoxy alcohol unit to give a cycloheptanoid ring incorporating syn-1,2-dihydroxylated functionality. Unusually, these carbocyclizations take place at the less substituted epoxide carbon atom of 2,3-epoxy alcohols, to the effective exclusion of alternative modes of cyclization. Chelation control is invoked to account for the highly efficient 7-endo-tet processes. Those processes occur at the expense of the normally more favored 6-exo-tet cyclizations. The little used Lewis acids SnBr4 and Sn(OTf)(2) are shown to be effective in promoting acetylenic epoxy alcohol cyclizations. The effect of the relative configuration of the epoxy alcohol unit upon the outcome of the cyclization was studied.

  DOI：

  10.1021/jo980986j
• 作为产物：
  描述：

  2-甲基-1,3-环戊二酮 在 叔丁基过氧化氢 、 sodium hydroxide 、 vanadyl acetylacetonate 、 potassium iodide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 8.0h， 生成 3-oxiranyl-3-hydroxy-2-methyl-2-(2-methyl-2-propenyl)cyclopentan-1-one
  参考文献：
  名称：

  Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols:  Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-Endo-Tet Ring Closures

  摘要：

  The stereocontrolled construction of cycloheptanoid ring systems, relevant to sesquiterpenes and diterpenes of biological activity, is described. A new and highly efficient cyclization methodology provides stereocontrolled routes to polyfunctionalized and hydroxylated cycloheptanoid (and cyclohexanoid) rings. An alkyne or alkene terminus is shown to cyclize onto a 2,3-epoxy alcohol unit to give a cycloheptanoid ring incorporating syn-1,2-dihydroxylated functionality. Unusually, these carbocyclizations take place at the less substituted epoxide carbon atom of 2,3-epoxy alcohols, to the effective exclusion of alternative modes of cyclization. Chelation control is invoked to account for the highly efficient 7-endo-tet processes. Those processes occur at the expense of the normally more favored 6-exo-tet cyclizations. The little used Lewis acids SnBr4 and Sn(OTf)(2) are shown to be effective in promoting acetylenic epoxy alcohol cyclizations. The effect of the relative configuration of the epoxy alcohol unit upon the outcome of the cyclization was studied.

  DOI：

  10.1021/jo980986j

文献信息

• Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols:  Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-<i>Endo-Tet</i> Ring Closures
  作者：Charles M. Marson、Jane McGregor、Afzal Khan、Trevor J. Grinter

  DOI：10.1021/jo980986j

  日期：1998.10.1

  The stereocontrolled construction of cycloheptanoid ring systems, relevant to sesquiterpenes and diterpenes of biological activity, is described. A new and highly efficient cyclization methodology provides stereocontrolled routes to polyfunctionalized and hydroxylated cycloheptanoid (and cyclohexanoid) rings. An alkyne or alkene terminus is shown to cyclize onto a 2,3-epoxy alcohol unit to give a cycloheptanoid ring incorporating syn-1,2-dihydroxylated functionality. Unusually, these carbocyclizations take place at the less substituted epoxide carbon atom of 2,3-epoxy alcohols, to the effective exclusion of alternative modes of cyclization. Chelation control is invoked to account for the highly efficient 7-endo-tet processes. Those processes occur at the expense of the normally more favored 6-exo-tet cyclizations. The little used Lewis acids SnBr4 and Sn(OTf)(2) are shown to be effective in promoting acetylenic epoxy alcohol cyclizations. The effect of the relative configuration of the epoxy alcohol unit upon the outcome of the cyclization was studied.