5-hydroxymethyl-3-methyl-δ-valerolactone | 247246-42-0

• 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: 5-hydroxymethyl-3-methyl-δ-valerolactone
• 英文别名: 6-(Hydroxymethyl)-4-methyloxan-2-one
• CAS: 247246-42-0
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: QXJCAXZPLMIRLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：

  5-hydroxymethyl-3-methyl-δ-valerolactone 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 5-formyl-3-methyl-δ-valerolactone
  参考文献：
  名称：

  A general synthesis of 2- or 3-alkyl substituted 5-hydroxymethyl-δ-valerolactones, precursors of 5-formyl-δ-valerolactones, via lithiated N-allyl(bisdimethylamino)-N-methylphosphoramide carbanions

  摘要：

  A convenient strategy is reported for the synthesis of 2- or 3-alkylsubstituted 5-hydroxymethyl and 5-formyl-delta-valerolactones, which are very useful starting blocks for the total synthesis of leukotrienes and lactonic pheromones, It has been found that lithiated enephosphoramide ambident anions reacted exclusively in the gamma position with 2,3-O-isopropylidene glycerol triflate to give corresponding alkylated enephosphoramides by a C3-C3 backbone connection. Enephosphoramide group was further selectively hydrolyzed in the presence of isopropylidene function in mild acidic conditions and led to expected aldehydes in high yields. Oxidation of these aldehydes using silver oxide or potassium permanganate afforded corresponding acids. Further hydrolysis of the isopropylidene group led to unstable dihydroxyacids which directly lactonized. The latter were converted to 5-formyl-delta-valerolactones using PDC oxidant. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00269-7
• 作为产物：
  描述：

  3-methyl-4-(2,2-dimethyl-1,3-dioxolan-4-yl)butanal 在 盐酸 、 sodium hydroxide 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 11.0h， 生成 5-hydroxymethyl-3-methyl-δ-valerolactone
  参考文献：
  名称：

  A general synthesis of 2- or 3-alkyl substituted 5-hydroxymethyl-δ-valerolactones, precursors of 5-formyl-δ-valerolactones, via lithiated N-allyl(bisdimethylamino)-N-methylphosphoramide carbanions

  摘要：

  A convenient strategy is reported for the synthesis of 2- or 3-alkylsubstituted 5-hydroxymethyl and 5-formyl-delta-valerolactones, which are very useful starting blocks for the total synthesis of leukotrienes and lactonic pheromones, It has been found that lithiated enephosphoramide ambident anions reacted exclusively in the gamma position with 2,3-O-isopropylidene glycerol triflate to give corresponding alkylated enephosphoramides by a C3-C3 backbone connection. Enephosphoramide group was further selectively hydrolyzed in the presence of isopropylidene function in mild acidic conditions and led to expected aldehydes in high yields. Oxidation of these aldehydes using silver oxide or potassium permanganate afforded corresponding acids. Further hydrolysis of the isopropylidene group led to unstable dihydroxyacids which directly lactonized. The latter were converted to 5-formyl-delta-valerolactones using PDC oxidant. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00269-7

文献信息

• A general synthesis of 2- or 3-alkyl substituted 5-hydroxymethyl-δ-valerolactones, precursors of 5-formyl-δ-valerolactones, via lithiated N-allyl(bisdimethylamino)-N-methylphosphoramide carbanions
  作者：Philippe Coutrot、Claude Grison、Catherine Bômont

  DOI：10.1016/s0022-328x(99)00269-7

  日期：1999.9

  A convenient strategy is reported for the synthesis of 2- or 3-alkylsubstituted 5-hydroxymethyl and 5-formyl-delta-valerolactones, which are very useful starting blocks for the total synthesis of leukotrienes and lactonic pheromones, It has been found that lithiated enephosphoramide ambident anions reacted exclusively in the gamma position with 2,3-O-isopropylidene glycerol triflate to give corresponding alkylated enephosphoramides by a C3-C3 backbone connection. Enephosphoramide group was further selectively hydrolyzed in the presence of isopropylidene function in mild acidic conditions and led to expected aldehydes in high yields. Oxidation of these aldehydes using silver oxide or potassium permanganate afforded corresponding acids. Further hydrolysis of the isopropylidene group led to unstable dihydroxyacids which directly lactonized. The latter were converted to 5-formyl-delta-valerolactones using PDC oxidant. (C) 1999 Elsevier Science S.A. All rights reserved.