(3R,5R)-5-(hydroxymethyl)-3,5-dimethyldihydrofuran-2(3H)-one | 950489-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,5R)-5-(hydroxymethyl)-3,5-dimethyldihydrofuran-2(3H)-one
• 英文别名: (3R,5R)-5-(hydroxymethyl)-3,5-dimethyloxolan-2-one
• CAS: 950489-54-0
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: CWOZARUPLCXUTC-IYSWYEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5R)-5-(hydroxymethyl)-3,5-dimethyldihydrofuran-2(3H)-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,4R)-2,4-dimethyl-5-oxotetrahydrofuran-2-carbaldehyde
  参考文献：
  名称：

  Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations

  摘要：

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.028
• 作为产物：
  描述：

  (2R,4R)-2,4-dimethyl-5-oxotetrahydrofuran-2-carboxylic acid 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以0.085 g的产率得到(3R,5R)-5-(hydroxymethyl)-3,5-dimethyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Preparation of enantiopure 3,5,5-trialkyl-γ-butyrolactones by diastereospecific 5-endo halo lactonizations

  摘要：

  A new preparation of 3,5,5-trialkyl-gamma-butyrolactones of defined absolute configuration is reported. This method involves the diastereoselective alkylation of 3,4-ethylenic acids after incorporation of a chiral Evans auxiliary, and then after separation of the two diastereomers and hydrolysis of the auxiliary, stereospecific halo lactonizations. This method was applied to the preparation of a natural product, present in a sponge. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.028