2-methyl-4-(3,4-methylenedioxyphenylmethylene)-5(4H)-oxazolone | 60470-83-9

• 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: 2-methyl-4-(3,4-methylenedioxyphenylmethylene)-5(4H)-oxazolone
• 英文别名: (Z)-4-(benzo[d][1,3]dioxol-5-ylmethylene)-2-methyloxazol-5(4H)-one；4-(3',4'-methylenedioxybenzylidene)-2-methyl-5(4H)-oxazolone；2-methyl-4-((Z)-piperonyliden)-4H-oxazol-5-one；2-Methyl-4-((Z)-piperonyliden)-4H-oxazol-5-on；2-Methyl-4-piperonylidene-2-oxazoline-5-one；(4Z)-4-(1,3-benzodioxol-5-ylmethylidene)-2-methyl-1,3-oxazol-5-one
• CAS: 60470-83-9
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: YIPBMFCRAFHCPQ-WTKPLQERSA-N

物化性质

• 熔点：
  183 °C
• 沸点：
  358.0±52.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(3,4-methylenedioxyphenylmethylene)-5(4H)-oxazolone 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-benzo[1,3]dioxol-5-ylmethyl-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus

  摘要：

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

  DOI：

  10.1021/jm960062t
• 作为产物：
  描述：

  胡椒醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 反应 3.5h， 以71%的产率得到2-methyl-4-(3,4-methylenedioxyphenylmethylene)-5(4H)-oxazolone
  参考文献：
  名称：

  A Modified Synthesis of (±)-β-Aryllactic acids

  摘要：

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。

  DOI：

  10.1055/s-1992-26228

文献信息

• Rapid synthesis of the core scaffold of crinane and haemanthamine through a multi-component approach
  作者：Nicholas P. Massaro、Joshua G. Pierce

  DOI：10.1016/j.tetlet.2021.153201

  日期：2021.7

  A rapid synthesis of the core structures of crinane and haemanthamine has been developed, enabled by a multicomponent approach. This work constitutes a formal synthesis of crinane and sets the stage for access to both families of natural products and key analogues. A key highlight of the approach is the modularity of the core synthesis, overcoming existing challenges for these scaffolds and providing

  通过多组分方法，已经开发了一种快速合成 crinane 和 haemanthamine 核心结构的方法。这项工作构成了对 crinane 的正式综合，并为获取天然产品和关键类似物家族奠定了基础。该方法的一个关键亮点是核心合成的模块化，克服了这些支架现有的挑战，并提供了探索位点选择性氧化以扩大可从常见中间体获得的分子范围的途径。
• Tyagi, O D; Boll, P M; Parmar, V S, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 851 - 854
  作者：Tyagi, O D、Boll, P M、Parmar, V S、Taneja, Poonam、Singh, S K

  DOI：——

  日期：——
• Pseudo-peptides derived from isomannide: inhibitors of serine proteases
  作者：Thalita G. Barros、Sergio Pinheiro、J. S. Williamson、Amílcar Tanuri、M. Gomes、Helena S. Pereira、R. M. Brindeiro、José B. A. Neto、O. A. C. Antunes、Estela M. F. Muri

  DOI：10.1007/s00726-009-0273-4

  日期：2010.3

  In this paper, we describe the synthesis of a novel class of pseudo-peptides derived from isomannide and several oxazolones as potential inhibitors of serine proteases as well as preliminary pharmacological assays for hepatitis C. Hepatitis C, dengue and West Nile fever are among the most important flaviviruses that share one important serine protease enzyme. Serine proteases belong to the most studied class of proteolytic enzymes and are a primary target in the drug development field. Several pseudo-peptides were obtained in good yields from the reaction of isomannide and oxazolones, and their anti-HCV potential using the HCV replicon-based assay was shown.
• Three Distinct Reactions of 3,4-Dihydroisoquinolines with Azlactones:  Novel Synthesis of Imidazoloisoquinolin-3-ones, Benzo[<i>a</i>]quinolizin-4-ones, and Benzo[<i>d</i>]azocin-4-ones
  作者：Rattana Worayuthakarn、Nopporn Thasana、Somsak Ruchirawat

  DOI：10.1021/ol062429m

  日期：2006.12.1

  [GRAPHICS]A facile and direct synthetic entry to tricyclic imidazoloisoquinolin-3-ones and benzo[a] quinolizin-4-ones is reported based on the ring annulation of 1-unsubstituted and 1-substituted dihydroisoquinolines with azlactones under neutral conditions in a one-step procedure. Bicyclic 2,3dihydrobenzo[d]azocin-4-ones were also prepared using simple azlactone and 1-substituted dihydroisoquinolines in a one-pot reaction.
• Subhashini, N J Prameela; Hanumanthu, P, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 4, p. 427 - 429
  作者：Subhashini, N J Prameela、Hanumanthu, P

  DOI：——

  日期：——