5,6-dihydro-4-hydroxy-6-(1-methylethyl)-2-pyrone | 55848-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5,6-dihydro-4-hydroxy-6-(1-methylethyl)-2-pyrone
• 英文别名: 4-Hydroxy-2-propan-2-yl-2,3-dihydropyran-6-one
• CAS: 55848-88-9
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: RTAUKOBQUYQBAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  5,6-dihydro-4-hydroxy-6-(1-methylethyl)-2-pyrone 、 硫酸二甲酯 以84%的产率得到
  参考文献：
  名称：

  IZAWA T.; MUKAIYAMA T., CHEM. LETT., 1975, NO 2, 161-164

  摘要：

  DOI：
• 作为产物：
  描述：

  双乙烯酮 、 异丁醛 以22%的产率得到
  参考文献：
  名称：

  IZAWA T.; MUKAIYAMA T., CHEM. LETT., 1975, NO 2, 161-164

  摘要：

  DOI：

文献信息

• Mechanism of Hydrolysis and Structure–Stability Relationship of Enaminones as Potential Prodrugs of Model Primary Amines
  作者：Vijay H. Naringrekar、Valentino J. Stella

  DOI：10.1002/jps.2600790213

  日期：1990.2

  compound, suggesting that the rate-controlling step in the hydrolysis of the enaminones was the proton addition to the vinyl carbon of the enaminone. Enaminones formed with cyclic 1,3-dicarbonyl compounds were significantly more stable than those formed with structurally similar acyclic compounds. Based on chemical stability considerations alone, enaminones do not appear to be good candidates as prodrugs of

  这项工作的目的是研究烯胺酮（伯胺和1,3-二羰基化合物之间形成的一类烯胺）的化学性质和结构稳定性关系，并评估其作为伯胺前药的潜在用途。发现烯胺酮的酸催化降解对用于形成烯胺酮的1，3-二羰基化合物的结构的微小差异非常敏感，但是对烯胺酮的胺部分的变化相对不敏感。发现烯胺酮水解的速率和1，3-二羰基化合物的pKa之间存在相关性，这表明烯胺酮水解的速率控制步骤是质子烯在烯胺酮的乙烯基碳上的加成。与环1形成的烯胺 3-二羰基化合物比用结构相似的无环化合物形成的化合物明显更稳定。仅基于化学稳定性的考虑，烯胺酮作为伯胺的前药似乎不适合作为候选药物。但是，有证据表明，在胺和1，3-酮酸酯或内酯之间形成的烯胺酮可能会受到酶催化的降解。可能需要进行进一步的研究，以设计因触发酶促反应而失稳的烯胺酮（该酶导致共轭损失）（例如，酯或内酯水解或氧化/还原事件）。在胺和1，3-酮酸酯或内酯之间形成的烯胺酮可能会受到酶催
• Enaminones as potential prodrugs of primary and secondary amines
  申请人：Merck & Co., Inc.

  公开号：EP0214009A2

  公开（公告）日：1987-03-11

  Novel enzymatically labile enaminones useful as potential prodrugs of primary and secondary amines are disclosed. Also, disclosed herein are compositions comprising said amines and methods of administering said composition to warm-blooded animals.

  本发明公开了可作为伯胺和仲胺潜在原药的新型酶标记烯酮。此外，本文还公开了包含所述胺的组合物以及将所述组合物用于温血动物的方法。
• HIV PROTEASE INHIBITORS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1112269A2

  公开（公告）日：2001-07-04
• ENZYMATIC SYNTHESIS OF KAVALACTONES AND FLAVOKAVAINS
  申请人：Whitehead Institute for Biomedical Research

  公开号：US20220002769A1

  公开（公告）日：2022-01-06

  Disclosed are methods, compositions, proteins, nucleic acids, cells, vectors, compounds, reagents, and systems for the preparation of kavalactones, flavokavains, and kavalactone and flavokavain biosynthetic intermediates using enzymes expressed in heterologous host cells, such as microorganisms or plants, or using in vitro enzymatic reactions. This invention also provides for the expression of the enzymes by recombinant cell lines and vectors. Furthermore, the enzymes can be components of constructs such as fusion proteins. The kavalactones produced can be utilized to treat anxiety disorder, insomnia, and other psychological and neurological disorders. The flavokavains produced can be utilized to treat various cancers including colon, bladder, and breast cancers.
• [EN] HIV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTEASE DU VIH
  申请人：WARNER LAMBERT CO

  公开号：WO2000015634A2

  公开（公告）日：2000-03-23

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.