sodium salt of 3-(hydroxymethylene)tetrahydropyran-2-one | 53761-41-4

• 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: sodium salt of 3-(hydroxymethylene)tetrahydropyran-2-one
• 英文别名: sodium 3-(hydroxymethylene)tetrahydro-2H-pyran-2-one；sodio-2-hydroxymethylenepentan-5-olide
• CAS: 53761-41-4
• 化学式: C₆H₇O₃*Na
• 分子量: 150.11
• InChiKey: HHDOIKIRKDTUTB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.43
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.36
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  sodium salt of 3-(hydroxymethylene)tetrahydropyran-2-one 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-chloro-3-(3-chloropropyl)-8-methoxyquinoline
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 1. 1-Aryl-4-methylpyrrolo[3,2-c]quinolines as conformationally restrained analogs of 4-(arylamino)quinolines

  摘要：

  The 4-(arylamino)quinoline 4, previously described as an antiulcer compound, is shown to be an inhibitor of the gastric (H+/K+)-ATPase. It is postulated that 1-arylpyrrolo[3,2-c]quinolines 6 act as conformationally restrained analogues of 4. A series of derivatives of 6 has been prepared and shown to be potent inhibitors of the target enzyme in vitro. Substitution in the ortho position of the aryl ring is important for activity. Unsaturation in the 5-membered ring makes little difference, but introduction of heteroatoms into the same ring markedly reduces activity. In more detailed kinetic experiments, 15c and 4 both show reversible, K(+)-competitive binding to the enzyme, with submicromolar Ki values. The compounds appear to act at the lumenal face of the enzyme and to require protonation for activity. Several compounds in the series are shown to be potent inhibitors of pentagastrin-stimulated acid secretion in the rat.

  DOI：

  10.1021/jm00164a010
• 作为产物：
  描述：

  delta-戊内酯 、 甲酸乙酯 在 sodium 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以93%的产率得到sodium salt of 3-(hydroxymethylene)tetrahydropyran-2-one
  参考文献：
  名称：

  Nucleophilic Vinylic Substitution on α-Tosyloxymethylene Lactones

  摘要：

  通过δ-戊内酯和乙酸乙酯的克莱森缩合反应获得了3-羟甲基四氢-2H-吡喃-2-酮的钠盐（V），并将其转化为磺酸盐和羧酸盐IV、VII-X，这些化合物可以作为纯的E异构体或E和Z异构体的混合物得到；混合物经过色谱分离。研究了α-对甲苯磺酰氧亚甲基内酯II、III和IV与芳香硫醇、叠氮阴离子、二级胺和钠烯醇酸盐XI、XII和V的取代反应。从亲核烯丙基取代（SNV）的机理角度讨论了这种取代反应的立体化学结果。

  DOI：

  10.1135/cccc19931607

文献信息

• The preparation of synthetic analogues of strigol
  作者：Alan W. Johnson、Gopala Gowada、Ahmed Hassanali、John Knox、Sam Monaco、Zia Razavi、Gerald Rosebery

  DOI：10.1039/p19810001734

  日期：——

  A range of analogues of the natural germination stimulant, strigol, for parasitic weeds of the genera Striga and Orobanche, has been prepared. Most of the products contain an α-formyl-γ-lactone (or α-formyl-γ-lactam) grouping attached through an enol-ether linkage to the 5-position of a but-2-enolide. Some have shown sufficiently high activities as to warrant large-scale field trials.

  已经制备了用于Striga和Orobanche属的寄生杂草的天然发芽刺激剂strigol的一系列类似物。大多数产物包含通过烯醇-醚键连接至but-2-enolide的5-位的α-甲酰基-γ-内酯（或α-甲酰基-γ-内酰胺）基团。有些已经显示出足够高的活动量，可以进行大规模的现场试验。
• A Method for the Preparation of β-Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism
  作者：Reyno R. S.、Akash Sugunan、Ranganayakulu S.、Cherumuttathu H. Suresh、Goreti Rajendar

  DOI：10.1021/acs.orglett.9b04531

  日期：2020.2.7

  An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the reactivity of aliphatic amines in protic solvents and aromatic amines in aprotic solvents. While the

  证明了一种制备β-氨基-α，β-不饱和羰基化合物的有效方法。由羰基化合物制备稳定的3-氧代-烯醇钠盐，并在酸和干燥剂的存在下与胺反应。DFT研究揭示了质子溶剂中脂族胺与质子溶剂中芳族胺反应性的对比机制。前者通过形成亚胺进行，而后者通过迈克尔加成消除机理进行。
• Thiophosphates and Selenophosphates in Organic Synthesis. A New Approach to Exocyclic Olefins and Bicyclic Enones
  作者：Aleksandra Skowronska、Ewa Krawczyk、Marek Koprowski、Piotr Dybowski

  DOI：10.1080/10426509608046285

  日期：1996.2.1