(2'R,5R)-5-(2,3-dihydroxypropyl)-4,5-dihydro-2(3H)-furanone | 208766-17-0

• 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: (2'R,5R)-5-(2,3-dihydroxypropyl)-4,5-dihydro-2(3H)-furanone
• 英文别名: (5R)-5-[(2R)-2,3-dihydroxypropyl]oxolan-2-one
• CAS: 208766-17-0
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: GDPXUOFKFLOLEA-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2'R,5R)-5-(2,3-dihydroxypropyl)-4,5-dihydro-2(3H)-furanone 在 三氟甲磺酸三甲基硅酯 、 四丁基溴化铵 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 (5R)-5-[(2R)-2,3-bis(phenylmethoxy)propyl]oxolan-2-one
  参考文献：
  名称：

  Synthesis of a Butyrolactone Precursor of an Algae Nonaether from an Enantiopure Glycol Obtained by Hoppe's Chemistry

  摘要：

  Homoallyl carbamate 20, (-)-sparteine, and sBuLi gave a lithium derivative which was formylated with DMF giving the crude aldehydocarbamate 19. With Lithium aluminum hydride in refluxing THF, this compound provided diol 22 in 90% overall yield and with 96% ee. This material was carried on to the gamma-lactone monoethers 13 (benzyl ether) or 14 (trityl ether). These compounds should be precursors for synthesizing the naturally occurring nonaether 7.

  DOI：

  10.1002/(sici)1099-0690(199806)1998:6<1023::aid-ejoc1023>3.0.co;2-3
• 作为产物：
  描述：

  methyl (6R)-6,7-dihydroxy-4-oxoheptanoate 在 盐酸 、 sodium tetrahydroborate 、 三乙基硼 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.5h， 生成 (2'R,5R)-5-(2,3-dihydroxypropyl)-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  Synthesis of a Butyrolactone Precursor of an Algae Nonaether from an Enantiopure Glycol Obtained by Hoppe's Chemistry

  摘要：

  Homoallyl carbamate 20, (-)-sparteine, and sBuLi gave a lithium derivative which was formylated with DMF giving the crude aldehydocarbamate 19. With Lithium aluminum hydride in refluxing THF, this compound provided diol 22 in 90% overall yield and with 96% ee. This material was carried on to the gamma-lactone monoethers 13 (benzyl ether) or 14 (trityl ether). These compounds should be precursors for synthesizing the naturally occurring nonaether 7.

  DOI：

  10.1002/(sici)1099-0690(199806)1998:6<1023::aid-ejoc1023>3.0.co;2-3

文献信息

• Synthesis of a Butyrolactone Precursor of an Algae Nonaether from an Enantiopure Glycol Obtained by Hoppe's Chemistry
  作者：Markus Menges、Reinhard Brückner

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1023::aid-ejoc1023>3.0.co;2-3

  日期：1998.6

  Homoallyl carbamate 20, (-)-sparteine, and sBuLi gave a lithium derivative which was formylated with DMF giving the crude aldehydocarbamate 19. With Lithium aluminum hydride in refluxing THF, this compound provided diol 22 in 90% overall yield and with 96% ee. This material was carried on to the gamma-lactone monoethers 13 (benzyl ether) or 14 (trityl ether). These compounds should be precursors for synthesizing the naturally occurring nonaether 7.