(2S,5R)-2-hydroxy-5-methyl-δ-valerolactone | 118648-47-8

• 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: (2S,5R)-2-hydroxy-5-methyl-δ-valerolactone
• 英文别名: (2R/S,5R/S)-2,5-dihydroxyhexanoic acid δ-lactone；3-hydroxy-6-methyl-tetrahydro-pyran-2-one；2,5-Dihydroxyhexansaeure-δ-lacton；3-Hydroxy-6-methyloxan-2-one
• CAS: 118648-47-8
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: NWOULGUVRYNVGI-UHFFFAOYSA-N

物化性质

• 沸点：
  259.8±23.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (2S,5R)-2-hydroxy-5-methyl-δ-valerolactone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 己烷-1,2,5-三醇
  参考文献：
  名称：

  950.抗生素的碳水化合物成分。第一部分。碱对去氨水的降解：其在位置5的绝对构型

  摘要：

  DOI：

  10.1039/jr9610004831
• 作为产物：
  描述：

  丁位己内酯 在 咪唑 、 盐酸 、 甲醇 、 二氯甲烷 、 双(三甲基硅烷基)氨基钾 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (2S,5R)-2-hydroxy-5-methyl-δ-valerolactone
  参考文献：
  名称：

  Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l-Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

  摘要：

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.

  DOI：

  10.1021/jo9515081

文献信息

• PRODUCTION OF 2,4-HEXADIENOIC ACID AND 1,3-PENTADIENE FROM 6-METHYL-5,6-DIHYDRO-2-PYRONE
  申请人：Dumesic James A.

  公开号：US20120116119A1

  公开（公告）日：2012-05-10

  Described is a method of making sorbic acid, pentadiene, or 3-penten-2-one. The method includes partially hydrogenating 4-hydroxy-6-methyl-2-pyrone (HMP) to yield 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (4-DHMMP). Then, if 3-penten-2-one is desired, thermally decomposing the 4-DHMMP to yield 3-penten-2-one. If sorbic acid or pentadiene are desired, the 4-DHMMP is hydrogenated to yield 4-hydroxy-6-methyltetrahydro-2-pyrone (4-HMTHP). The 4-HMTHP is then dehydrated by contacting it with a solid acid catalyst to yield parasorbic acid (PSA). The PSA can then be ring-opened by contacting it with a solid acid catalyst. The reaction conditions of the ring-opening reaction can be controlled to yield sorbic acid and/or pentadiene.

  描述了一种制备山梨酸、戊二烯或3-戊烯-2-酮的方法。该方法包括部分氢化4-羟基-6-甲基-2-吡喃酮（HMP）以得到5,6-二氢化-4-羟基-6-甲基-2H-吡喃-2-酮（4-DHMMP）。然后，如果需要3-戊烯-2-酮，则热分解4-DHMMP以得到3-戊烯-2-酮。如果需要山梨酸或戊二烯，则将4-DHMMP氢化以得到4-羟基-6-甲基四氢-2-吡喃酮（4-HMTHP）。然后，通过与固体酸催化剂接触使4-HMTHP脱水以得到对山梨酸（PSA）。然后可以通过与固体酸催化剂接触使PSA发生环开启反应。环开启反应的反应条件可以控制以得到山梨酸和/或戊二烯。
• US8404890B2
  申请人：——

  公开号：US8404890B2

  公开（公告）日：2013-03-26
• Enantiospecific Synthesis of (+)- and (−)-Ferruginine from <scp>l</scp>-Glutamic Acid. Synthesis of Tropanes <i>via</i> Intramolecular Iminium Ion Cyclization
  作者：Andrés S. Hernández、Adrian Thaler、Josep Castells、Henry Rapoport

  DOI：10.1021/jo9515081

  日期：1996.1.1

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.
• 950. Carbohydrate components of antibiotics. Part I. Degradation of desosamine by alkali: its absolute configuration at position 5
  作者：C. H. Bolton、A. B. Foster、M. Stacey、J. M. Webber

  DOI：10.1039/jr9610004831

  日期：——