6-methyl-chroman-2,4-dione | 620968-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-methyl-chroman-2,4-dione
• 英文别名: 6-Methyl-chroman-2,4-dion；6-Methylchromene-2,4-dione
• CAS: 620968-65-2
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: COORGVFNUOZLCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  332.4±42.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-chroman-2,4-dione 在 sodium hydroxide 作用下， 生成 5-甲基水杨酸
  参考文献：
  名称：

  Matsui; Ota, Nippon Kagaku Zasshi, 1957, vol. 78, p. 517,518

  摘要：

  DOI：
• 作为产物：
  描述：

  二(4-甲基苯基)丙二酸酯 在 三氯化铝 作用下， 生成 6-methyl-chroman-2,4-dione
  参考文献：
  名称：

  Zur Chemie des 4-Oxy-cumarins

  摘要：

  DOI：

  10.1007/bf00899270

文献信息

• Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C–H Activation
  作者：Yuqin Jiang、Pengfei Li、Jie Zhao、Bingxian Liu、Xingwei Li

  DOI：10.1021/acs.orglett.0c02618

  日期：2020.10.2

  The rhodium(III)-catalyzed coupling of C–H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C–H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol

  铑（III）催化的C–H底物与碘鎓碘化物的偶联已经实现了各种环状骨架的有效合成，其中碘鎓碘化物已被认为是有效且出色的卡宾前体。该反应系统适用于在轻度和氧化还原中性条件下的sp 2和sp 3 C–H底物。在克规模的反应中，催化剂的负载量可以低至0.5mol％。代表性产品在纳摩尔水平下对人癌细胞具有细胞毒性。
• Regio and diastereoselective lactonisation of enolisable 1,3-dicarbonyls by reaction with mesoionic 1,3-oxazolium-5-olates
  作者：Giovanni Grassi、Francesco Risitano、Francesco Foti、Massimiliano Cordaro、Giuseppe Bruno、Francesco Nicolò

  DOI：10.1039/b304560a

  日期：——

  The one-pot reaction of enolisable 1,3-dicarbonyls and N-methyl-1,3-oxazolium-5-olate derivatives provided enol lactones directly in good yield and with excellent regio- and diastereocontrol.

  可酰化的1,3-二酮和N-甲基-1,3-噁唑锂-5-醇衍生物的一锅反应直接提供了酮内酯，产率良好，并具有优异的区域选择性和非对映体选择性。
• Efficient Synthesis of Dihydrofurans with Sulfide Groups by Ceric(IV) Ammonium Nitrate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Vinyl Sulfides. Application to the Synthesis of Benzo[<i>b</i>]naphtho[2,3-<i>d</i>]furan-6,11-dione and First Total Synthesis of Millettocalyxins C and Pongamol Methyl Ether
  作者：Yong Rok Lee、Keon Yong Kang、Gun Joon Lee、Won Kyong Lee

  DOI：10.1055/s-2003-41023

  日期：——

  Ceric(IV) ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to vinyl sulfides afforded substituted dihydrofurans with sulfide groups in moderate yields. This new synthetic method has been applied to thesynthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione and furanoflavone natural products such as millettocalyxins C and pongol methyl ether.

  Ceric(IV) 硝酸铵介导的 1,3-二羰基与乙烯基硫化物的氧化环加成反应以中等收率提供了具有硫化物基团的取代二氢呋喃。这种新的合成方法已应用于苯并[b]萘并[2,3-d]呋喃-6,11-二酮和呋喃黄酮类天然产物如小米花萼素C、凤梨甲醚的合成。
• Synthesis of novel dihydrofuro[b]-pyridinone derivatives: oxidation coupling of 3-hydroxy-4(1H)-pyridinone with β-dicarbonyl compounds
  作者：Li-Xia Pei、Shi-Liang Huang、Yu-Dong Shen、Lin-Qun An、Zhi-Shu Huang、Yue-Ming Li、Lian-Quan Gu、Xian-Zhang Bu、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2005.05.078

  日期：2005.7

  Oxidation coupling of 3-hydroxy-4(1H)-pyridinone with β-dicarbonyl compounds led to unexpected dihydrofuro[b]-pyridinone derivatives, indicating an alternative pathway other than that with anilines or thiols. By this strategy, six novel dihydrofuro[b]-pyridinone derivatives were synthesized.

  3-羟基-4（1 H）-吡啶酮与β-二羰基化合物的氧化偶联导致意外的二氢呋喃并[ b ]-吡啶酮衍生物，这表明苯胺或硫醇以外的另一种途径。通过这种策略，合成了六种新颖的二氢呋喃并[ b ]-吡啶酮衍生物。
• A facile stereoselective synthesis of julolidine hybrid analogs via domino knoevenagel intramolecular hetero Diels–Alder reaction
  作者：Atanu Ghoshal、Asit R. Sarkar、R. Senthil kumaran、Subramanya Hegde、Govindaswamy Manickam、Jayadevan Jayashankaran

  DOI：10.1016/j.tetlet.2012.01.103

  日期：2012.4

  We have reported here a facile stereoselective synthesis of julolidine hybrid analogs by employing domino Knoevenagel intramolecular hetero Diels–Alder reaction on symmetrical 1,3-diones and unsymmetrical 1,3-diones It was found that the cycloaddition proceeded efficiently under microwave irradiation to afford highly stereoselective cycloadducts in good yields

  我们在这里报告了通过对对称的1,3-二酮和不对称的1,3-二酮采用多米诺骨牌Knoevenagel分子内杂Diels-Alder反应，轻松实现立体异构体合成的Julolidine杂合体的研究发现，环加成反应在微波辐照下有效进行，从而得到了立体选择性环加合物，收率高