(5R)-4-[(1R)-1,2-(dihydroxy)ethyl]-5-hydroxymethylfuran-2-(5H)-one | 506418-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5R)-4-[(1R)-1,2-(dihydroxy)ethyl]-5-hydroxymethylfuran-2-(5H)-one
• 英文别名: 2(5H)-Furanone, 4-[(1R)-1,2-dihydroxyethyl]-5-(hydroxymethyl)-, (5R)-；(2R)-3-[(1R)-1,2-dihydroxyethyl]-2-(hydroxymethyl)-2H-furan-5-one
• CAS: 506418-11-7
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: TVCNXYRWCIJNSX-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙酮 、 (5R)-4-[(1R)-1,2-(dihydroxy)ethyl]-5-hydroxymethylfuran-2-(5H)-one 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以86%的产率得到(5R)-4-[(1R)-1,2-(isopropylidenedioxy)ethyl]-5-hydroxymethylfuran-2-(5H)-one
  参考文献：
  名称：

  Efficient Desymmetrization of “Pseudo”-C₂-Symmetric Substrates:  Illustration in the Synthesis of a Disubstituted Butenolide from Arabitol

  摘要：

  A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.

  DOI：

  10.1021/jo026696r
• 作为产物：
  描述：

  L-(-)-arabitol 在 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 水 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 59.0h， 生成 (5R)-4-[(1R)-1,2-(dihydroxy)ethyl]-5-hydroxymethylfuran-2-(5H)-one
  参考文献：
  名称：

  Efficient Desymmetrization of “Pseudo”-C₂-Symmetric Substrates:  Illustration in the Synthesis of a Disubstituted Butenolide from Arabitol

  摘要：

  A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.

  DOI：

  10.1021/jo026696r

文献信息

• Efficient Desymmetrization of “<i>Pseudo</i>”-<i>C</i>₂-Symmetric Substrates:  Illustration in the Synthesis of a Disubstituted Butenolide from Arabitol
  作者：Bruno Linclau、A. James Boydell、Philip J. Clarke、Richard Horan、Claire Jacquet

  DOI：10.1021/jo026696r

  日期：2003.3.1

  A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.