diethyl 2-oxo-5-pentyl-tetrahydrofuran-3,4-dicarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2-oxo-5-pentyl-tetrahydrofuran-3,4-dicarboxylate
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: BGZZJAQWFBRERE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-oxo-5-pentyl-tetrahydrofuran-3,4-dicarboxylate 在 氢溴酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (+/-)-phaseolinic acid methyl ester
  参考文献：
  名称：

  Vicinal Dianion of Triethyl Ethanetricarboxylate: Syntheses of (±)-Lichesterinic Acid, (±)-Phaseolinic Acid, (±)-Nephromopsinic Acid, (±)-Rocellaric Acid, and (±)-Dihydroprotolichesterinic Acid

  摘要：

  The vicinal dianion 2 derived from triethyl ethanetricarboxylate reacted regioselectively with aldehydes and ketones at C(p) to provide paraconic acid derivatives 5a-f in moderate to high yields as mixtures of diastereoisomers. The paraconic acid derivatives 5e and 5f were utilized as the starting materials for the syntheses of (+/-)-lichesterinic acid (12), (+/-)-phaseolinic acid (13), (+/-)-nephromopsinic acid (14), (+/-)-rocellaric acid (15), and (+/-)-dihydroprotolichesterinic acid (16).

  DOI：

  10.1002/1522-2675(200211)85:11<3792::aid-hlca3792>3.0.co;2-q

文献信息

• Vicinal Dianion of Triethyl Ethanetricarboxylate: Syntheses of (±)-Lichesterinic Acid, (±)-Phaseolinic Acid, (±)-Nephromopsinic Acid, (±)-Rocellaric Acid, and (±)-Dihydroprotolichesterinic Acid
  作者：Manat Pohmakotr、Wacharee Harnying、Patoomratana Tuchinda、Vichai Reutrakul

  DOI：10.1002/1522-2675(200211)85:11<3792::aid-hlca3792>3.0.co;2-q

  日期：2002.11

  The vicinal dianion 2 derived from triethyl ethanetricarboxylate reacted regioselectively with aldehydes and ketones at C(p) to provide paraconic acid derivatives 5a-f in moderate to high yields as mixtures of diastereoisomers. The paraconic acid derivatives 5e and 5f were utilized as the starting materials for the syntheses of (+/-)-lichesterinic acid (12), (+/-)-phaseolinic acid (13), (+/-)-nephromopsinic acid (14), (+/-)-rocellaric acid (15), and (+/-)-dihydroprotolichesterinic acid (16).