methyl 4-oxo-4H-chromene-3-carboxylate | 93562-17-5

• 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: methyl 4-oxo-4H-chromene-3-carboxylate
• 英文别名: methyl 4-oxo-4H-1-benzopyran-3-carboxylate；3-methoxycarbonyl-4-oxo-4H-1-benzopyran；methyl 4-oxochromene-3-carboxylate
• CAS: 93562-17-5
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: ABRJVTYCAKRCGG-UHFFFAOYSA-N

物化性质

• 熔点：
  79-82 °C
• 沸点：
  311.3±42.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-oxo-4H-chromene-3-carboxylate 在 水 、 sodium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 黄烷酮
  参考文献：
  名称：

  将铜酸盐试剂添加到色酮上：通往2取代的chroman-4-ones的途径

  摘要：

  由与C-3相连的吸电子基团活化的苯并二氢呋喃酮（4-氧代-4H -1-苯并吡喃）经过有效的1,4-additon铜酸盐试剂，生成2,3-二取代的chroman-4-ones。通过在湿的二甲亚砜中用氯化钠处理，可以将苯甲酸三甲基苯甲酸酯的加成产物转化为2-取代的苯并四氢吡喃。

  DOI：

  10.1016/s0040-4020(01)88394-0
• 作为产物：
  描述：

  色酮-3-甲酸 在 氯化亚砜 作用下， 反应 16.0h， 生成 methyl 4-oxo-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Abdallah, H.; Gree, R.; Carrie, R., Bulletin de la Societe Chimique de France, 1984, vol. 2, # 7-8, p. 338 - 344

  摘要：

  DOI：

文献信息

• Metal-free access to 3-allyl-2-alkoxychromanones <i>via</i> phosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols
  作者：Ling Meng、Xiaoyong Chang、Zhenyang Lin、Jun (Joelle) Wang

  DOI：10.1039/d1ob00215e

  日期：——

  A phosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is established for the metal-free synthesis of 3-allyl-2-alkoxychromanones with high diastereoselectivity.

  一种磷膦催化的MBH碳酸酯和醇与香豆素的烯丙基化反应被建立，用于无金属合成高对映选择性的3-烯丙基-2-烷氧基香豆酮。
• Photocycloaddition reaction of methyl 2- and 3-chromonecarboxylates with various alkenes
  作者：Masami Sakamoto、Kazuya Yoshiwara、Fumitoshi Yagishita、Wataru Yoshida、Takashi Mino、Tsutomu Fujita

  DOI：10.1007/s11164-012-0656-0

  日期：2013.1

  The irradiation of methyl 2- and 3-chromonecarboxylate in the presence of various alkenes afforded cyclobutane type adducts, whose structures were established by X-ray structural analysis. Methyl 2-chromonecarboxylate showed higher photochemical reactivity than methyl 3-chromonecarboxylate, in which endo adducts were yielded as major products.

  在存在各种烯烃的情况下，甲基2-和3-色酮羧酸酯的辐照产生了环丁烷型加合物，其结构通过X射线结构分析确定。甲基2-色酮羧酸酯显示出比甲基3-色酮羧酸酯更高的光化学反应活性，其中内加合物为主要产物。
• Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A
  作者：Qiao Li、Chen Zhuang、Donghua Wang、Wei Zhang、Rongxuan Jia、Fengxia Sun、Yilin Zhang、Yunfei Du

  DOI：10.3762/bjoc.15.291

  日期：——

  The construction of the biologically interesting chromone skeleton was realized by PhIO-mediated dehydrogenation of chromanones under mild conditions. Interestingly, this method also found application in the synthesis of the naturally occurring frutinone A.

  通过PhIO介导的色酮在温和条件下的脱氢作用，实现了具有生物学意义的色酮骨架的构建。有趣的是，该方法还发现了在天然存在的果丁酮A合成中的应用。
• Therapeutic agents
  申请人：The Boots Company PLC

  公开号：EP0354693A1

  公开（公告）日：1990-02-14

  This invention relates to compounds of formula I wherein R₁ represents hydrogen or together with R₂ represents a bond; R₂ together with either one of R₁ and R₃ represents a bond; R₃ together with either one of R₂ and R₄ represents a bond; R₄ represents hydrogen or together with R₃ represents a bond; R₅ represents hydrogen or methyl; R₆ represents hydrogen, halo, a C₂₋₆ alkanoyl group, a C₂₋₆ alkoxycarbonyl group, a C₁₋₆ alkylthio group, a C₁₋₆ alkylsulphinyl group, a C₁₋₆ alkylsulphonyl group, carbamoyl, carboxy, or R₅ and R₆ together with the carbon atom to which they are attached represent a cyclopropyl group; R₇ represents hydrogen, halo, trifluoromethyl, methoxy, a C₁₋₆ alkyl group, a C₁₋₆ alkylthio group or a C₁₋₆ alkylsulphinyl group; R₈ represents hydrogen, halo or trifluoromethyl; R₉ and R₁₀, which may be the same or different, each represent halo; or R₉ represents hydrogen and R₁₀ represents hydrogen, halo, trifluoromethyl, hydroxy, nitro, a C₂₋₆ alkanoyloxy group, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group, which have immunomodulatory activity. Compositions containing these compounds and processes to make them are also disclosed.

  这项发明涉及具有以下结构的化合物，其中R₁代表氢或与R₂一起代表键；R₂与R₁或R₃中的任一者一起代表键；R₃与R₂或R₄中的任一者一起代表键；R₄代表氢或与R₃一起代表键；R₅代表氢或甲基；R₆代表氢、卤素、C₂₋₆烷酰基、C₂₋₆烷氧羰基、C₁₋₆烷基硫基、C₁₋₆烷基砜基、C₁₋₆烷基砜基、氨基甲酰基、羧基，或R₅和R₆与它们连接的碳原子一起代表环丙基；R₇代表氢、卤素、三氟甲基、甲氧基、C₁₋₆烷基、C₁₋₆烷基硫基或C₁₋₆烷基砜基；R₈代表氢、卤素或三氟甲基；R₉和R₁₀，可以相同也可以不同，每个代表卤素；或R₉代表氢，R₁₀代表氢、卤素、三氟甲基、羟基、硝基、C₂₋₆烷酰氧基、C₁₋₆烷基或C₁₋₆烷氧基，具有免疫调节活性。还公开了含有这些化合物的组合物和制备它们的方法。
• Silver(I)-Catalyzed Enantioselective [3+2]-Cycloaddition Reaction of α-Silylimines: A Facile Route to Quaternary-Carbon-Rich Scaffolds
  作者：Naredla Kesava-Reddy、Christopher Golz、Carsten Strohmann、Kamal Kumar

  DOI：10.1002/chem.201604793

  日期：2016.12.19

  A silver‐catalyzed highly enantioselective 1,3‐dipolar cycloaddition reaction of α‐silylimines with pyrone‐based trisubstituted olefins was developed affording bi‐ and tricyclic α‐quaternary‐carbon‐rich pyrano‐pyrrolidines in excellent yields. The tricyclic benzopyrone adducts thus obtained were efficiently transformed into highly complex tetracyclic scaffolds supporting four consecutive stereogenic

  已开发出一种银催化的α-甲硅烷基苯胺与吡喃基三取代烯烃的高对映选择性1,3-偶极环加成反应，从而以优异的收率提供了双环和三环的富含α-季碳的吡喃吡咯烷。由此获得的三环苯并吡喃酮加合物被有效地转化为高度复杂的四环支架，该支架支撑具有四个季碳的四个连续的立体异构中心。