(+/-)-4c-methyl-5-oxo-2r-tridecyl-tetrahydro-furan-3c-carboxylic acid

• 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: (+/-)-4c-methyl-5-oxo-2r-tridecyl-tetrahydro-furan-3c-carboxylic acid
• 英文别名: (+/-)-4c-Methyl-5-oxo-2r-tridecyl-tetrahydro-furan-3c-carbonsaeure；Nephromopsic acid；(2S,3S,4R)-4-methyl-5-oxo-2-tridecyloxolane-3-carboxylic acid
• 化学式: C₁₉H₃₄O₄
• 分子量: 326.477
• InChiKey: WLGALFYTFVOQPY-IKGGRYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (+/-)-4c-methyl-5-oxo-2r-tridecyl-tetrahydro-furan-3c-carboxylic acid 以 乙醚 为溶剂， 生成 methyl (-)-dihydro-allo-protolichesterinate
  参考文献：
  名称：

  (-)-Allo-pertusaric acid 和 (-)-dihydropertusaric acid 来自地衣 Pertusaria albescens

  摘要：

  摘要 已经通过光谱和化学方法阐明了来自白百合地衣的两种γ-内酯羧酸、(-)-异位百日咳酸和(-)二氢百日咳酸的结构。已从 P. ophthalmiza 中分离出蒲公英和长链脂肪醇和脂肪酸的混合物。

  DOI：

  10.1016/s0031-9422(00)85500-4
• 作为产物：
  描述：

  diethyl 2-oxo-5-tridecyl-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 (+/-)-4c-methyl-5-oxo-2r-tridecyl-tetrahydro-furan-3c-carboxylic acid
  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

• Synthesis of dl-Lichesterinic Acid Methyl Ester
  作者：Eugene E. van Tamelen、Clyde E. Osborne、Shirley Rosenberg Bach

  DOI：10.1021/ja01622a055

  日期：1955.9
• Huneck, Siegfried; Takeda, Reiji, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 6, p. 842 - 854
  作者：Huneck, Siegfried、Takeda, Reiji

  DOI：——

  日期：——
• Asano; Azumi, Chemische Berichte, 1939, vol. 72, p. 35,39
  作者：Asano、Azumi

  DOI：——

  日期：——
• Asahina; Yasue, Chemische Berichte, 1937, vol. 70, p. 1053,1056
  作者：Asahina、Yasue

  DOI：——

  日期：——
• 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).