5-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione | 66607-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: isopropylidene 1,4-dioxaspiro(4.5)decan-8-ylidenemalonate；5-(1,4-dioxa-spiro[4.5]dec-8-ylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione；5-(1,4-dioxa-spiro[4,5]dec-8-ylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione；5-(1,4-dioxaspiro[4.5]decan-8-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 66607-06-5
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: PITZKUBANRXYNB-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C(Solv: ethanol (64-17-5))
• 沸点：
  520.6±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 盐酸 、 对苯二酚 作用下， 以 氯仿 、 苯 为溶剂， 反应 25.0h， 生成 10,10-ethylenedithio-3,3-dimethyl-14-trimethylsilyloxy-2,4-dioxadispiro(5.0.5.4)hexadec-14-ene-1,5-dione
  参考文献：
  名称：

  Bell, Vivien L.; Holmes, Andrew B.; Hsu, Shih-Ying, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1507 - 1514

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 1,4-环己二酮单乙二醇缩酮 在 吡啶 作用下， 反应 48.0h， 生成 5-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) againstFasciola hepatica

  摘要：

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.

  DOI：

  10.1021/jm100226t

文献信息

• Meldrum's Acids as Acylating Agents in the Catalytic Intramolecular Friedel−Crafts Reaction
  作者：Eric Fillion、Dan Fishlock、Ashraf Wilsily、Julie M. Goll

  DOI：10.1021/jo0483724

  日期：2005.2.1

  dialkyl thioether, aryl methyl ether, aryl TIPS and TBDPS ethers, nitrile- and nitro-substituted aryls, alkyl and aryl halides) for a variety of 5-benzyl (enolizable Meldrum's acids) and 5-benzyl-5-substituted Meldrum's acids (quaternized Meldrum's acids), forming 1-indanones and 2-substituted-1-indanones, respectively, are delineated. This method was further applied to the synthesis of 1-tetralones,

  据报道，金属三氟甲磺酸盐催化的梅德鲁姆酸衍生物使芳烃分子内发生弗里德尔-克来福特酰化反应。Meldrum的酸易于制备，功能化，处理和纯化。深入研究了由苄基麦德鲁姆酸合成多取代的1-茚满酮的方法，结果表明，在温和条件下，多种催化剂均能有效容纳多种官能团。各种化合物的范围，局限性和官能团耐受性（末端烯烃和炔烃，缩酮，二烷基醚，二烷基硫醚，芳基甲基醚，芳基TIPS和TBDPS醚，腈和硝基取代的芳基，烷基和芳基卤化物） 5-苄基（可烯醇化的Meldrum's酸）和5-苄基-5-取代的Meldrum's酸（季铵化的Meldrum's酸），描绘了分别形成1-茚满酮和2-取代-1-茚满酮的化合物。该方法进一步应用于1-四氢萘酮，1-苯并亚砜和有效的乙酰胆碱酯酶抑制剂多奈哌齐的合成。通过竞争实验，确定了各种苯并环酮的环化率与环大小的关系：1-四酮类化合物的形成要比1-茚满酮和1-苯并亚砜的形成要快，而1-苯甲酮的成环作用要比1-茚满酮要快。
• Synthesis of novel furo-pyran derivatives via reaction between an isocyanide and alkylidene-substituted Meldrum’s acid
  作者：Azizollah Habibi、Enayatollah Seikhhosseini Lori、Abbas Shockravi

  DOI：10.1016/j.tetlet.2008.12.082

  日期：2009.3

  An unexpected four-component (3+1) reaction of an alkyl isocyanide with alkylidene-substituted Meldrum’s acid in CH2Cl2 at room temperature produces imino-furopyranones in good yields. The structures of the products are deduced from their IR, 1H NMR, and 13C NMR spectra and by X-ray analysis. The products are structurally similar to 2H-furo[2,3-c]pyran-2-one natural products.

  室温下，烷基异氰化物与亚烷基取代的麦德鲁姆酸在CH 2 Cl 2中发生意外的四组分（3 + 1）反应，可生成高收率的亚氨基呋喃基吡喃酮。由它们的IR，1 H NMR和13 C NMR光谱以及通过X射线分析推导产物的结构。该产物在结构上类似于2 H-呋喃[2，3 - c ]吡喃-2-酮天然产物。
• ANTAGONISTS OF PGD2 RECEPTORS
  申请人：Stearns Brian Andrew

  公开号：US20100298368A1

  公开（公告）日：2010-11-25

  Described herein are compounds and pharmaceutical compositions containing such compounds that modulate the PGD 2 activated chemoattractant receptor-homologous molecule expressed on TH 2 cells (CRTH2). Also described herein are methods of using such CRTH2 modulators, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other PGD 2 -dependent or PGD 2 mediated conditions or diseases.

  本文描述了一些化合物和含有这些化合物的药物组合物，这些化合物能够调节PGD2激活的TH2细胞表达的趋化因子受体同源分子（CRTH2）。本文还描述了使用这种CRTH2调节剂的方法，单独或与其他化合物结合，用于治疗呼吸系统、心血管系统和其他依赖于PGD2或由PGD2介导的疾病或病情。
• [EN] ANTAGONISTS OF PGD2 RECEPTORS<br/>[FR] ANTAGONISTES DE RÉCEPTEURS PGD2
  申请人：AMIRA PHARMACEUTICALS INC

  公开号：WO2009061681A3

  公开（公告）日：2009-07-16
• MOCK G. A.; HOLMES A. B.; RAPHAEL R. A., TETRAHEDRON LETT. <TELE-AY>, 1977, NO 51, 4539-4540
  作者：MOCK G. A.、 HOLMES A. B.、 RAPHAEL R. A.

  DOI：——

  日期：——