2-(β-Hydroxyisopropyl)-1,3-dioxolane | 78782-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(β-Hydroxyisopropyl)-1,3-dioxolane
• 英文别名: 2-(propan-1-ol-2-yl)-1,3-dioxolane；2-(1,3-Dioxolan-2-yl)propan-1-ol
• CAS: 78782-07-7
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: BRBNVEFGUDIUHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(β-Hydroxyisopropyl)-1,3-dioxolane 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2-(2-Iodo-1-methylethyl)-1,3-dioxolane
  参考文献：
  名称：

  An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin

  摘要：

  An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin 1 is reported. The synthesis involves as a key step a copper(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe3 to 2-methyl-2-cyclohexen-1-one with the Feringa (S,R,R)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde 4. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis.

  DOI：

  10.1021/jo400399q
• 作为产物：
  描述：

  2-(2-propenyl)-1,3-dioxolane 在 双氧水 、 sodium acetate 、 二(3-甲基丁烷-2-基)硼烷 作用下， 以95%的产率得到2-(β-Hydroxyisopropyl)-1,3-dioxolane
  参考文献：
  名称：

  Hydroboration. 57. Hydroboration with 9-borabicyclo[3.3.1]nonane of alkenes containing representative functional groups

  摘要：

  DOI：

  10.1021/jo00333a009

文献信息

• Hydroboration. 57. Hydroboration with 9-borabicyclo[3.3.1]nonane of alkenes containing representative functional groups
  作者：Herbert C. Brown、Jackson Chen

  DOI：10.1021/jo00333a009

  日期：1981.9
• An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin
  作者：Ana L. Silva、Rubén A. Toscano、Luis A. Maldonado

  DOI：10.1021/jo400399q

  日期：2013.6.7

  An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin 1 is reported. The synthesis involves as a key step a copper(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe3 to 2-methyl-2-cyclohexen-1-one with the Feringa (S,R,R)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde 4. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis.