methyl 4-formyl-furan-3-carboxylate | 37656-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 4-formyl-furan-3-carboxylate
• 英文别名: methyl 4-formyl-3-furoate；Methyl 4-formylfuran-3-carboxylate
• CAS: 37656-24-9
• 化学式: C₇H₆O₄
• 分子量: 154.122
• InChiKey: BVSQSKLAZSWRKC-UHFFFAOYSA-N

物化性质

• 沸点：
  259.2±25.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-formyl-furan-3-carboxylate 在 N,N-二甲基丙烯基脲 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 0.5h， 生成 methyl 4-(4-diazo-1-hydroxy-3,5-dioxohexyl)-3-furancarboxylate
  参考文献：
  名称：

  对乙烯基类胡萝卜素和二烯之间的II型[3 + 4]环加成进行的探索性研究。

  摘要：

  乙烯基类化合物和呋喃之间的分子内II型[3 + 4]环加成反应是构建5-oxo-10-oxatricyclo [6.2.1.0（4,9）] undeca-3，8（11）-二烯的一种实用方法，包含两个反布雷特双键。这些三环系统功能齐全，可以最终加工成天然产物CP-263,114。铑稳定的乙烯基类胡萝卜素是通过四羧酸二铑催化乙烯基重氮乙酸酯的分解而生成的。通常认为[3 + 4]环加成是通过串联环丙烷化/ Cope重排发生的，尽管有证据表明，使用这些底物，[3 + 4]环加成可能以协同方式发生。

  DOI：

  10.1021/jo991959b
• 作为产物：
  描述：

  3,4-呋喃二羧酸二甲酯 在 草酰氯 、 dimethyl sulfide borane 、 二甲基亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl 4-formyl-furan-3-carboxylate
  参考文献：
  名称：

  Total synthesis of monosporascone and dihydromonosporascone

  摘要：

  首次合成单孢子酮的过程共分为五个步骤，总产率为57%。

  DOI：

  10.1039/c4ob00331d

文献信息

• Antifolates for the treatment of cardiovascular, inflammatory, neoplastic, autoimmune and related diseases in sublingual dosage units, film strips, or skin patches
  申请人：Nair Madhavan G.

  公开号：US20100260825A1

  公开（公告）日：2010-10-14

  New metabolism blocked antifolates and their salts are provided along with new indications (coronary heart disease, cardiovascular diseases, stroke and termination of tubal or ectopic pregnancy) and methods (sublingual dosage forms, filmstrips or patches) for their use and delivery. Sublingual dosage forms or trans-dermal patches of metabolically blocked entities of this invention offer superior alternatives to traditional oral dosage forms to achieve greater and predictable therapeutic efficacy, lower toxicity and to overcome drug resistance by virtue of elimination of oxidative deactivation and production of toxic metabolites. Metabolism blocked antifolates bearing a fluorinated benzene ring, a thiophene ring, a pyrrole ring, a furan ring or a 8-deazapteridine ring that are provided in this invention are not previously described. The use of metabolism blocked antifolates to terminate medically complicated pregnancies that are taught herein are new inventions targeted to eliminate drug related toxicity to the host and to enhance therapeutic efficacy.

  本发明提供了新的代谢阻断型抗叶酸剂及其盐，并提供了新的适应症（冠心病、心血管疾病、中风以及输卵管或异位妊娠的终止）和使用方法（舌下剂型、薄膜或贴片）以及其输送方式。本发明中代谢阻断型实体的舌下剂型或经皮贴片，相对于传统的口服剂型，提供了更优越的选择，以实现更大且可预测的治疗效果、更低的毒性，并通过消除氧化失活和产生有毒代谢物来克服药物抵抗。本发明提供的带有氟苯环、噻吩环、吡咯环、呋喃环或8-脱氨嘌呤环的代谢阻断型抗叶酸剂在先前并未描述。本发明中教授的使用代谢阻断型抗叶酸剂来终止医疗复杂的妊娠是新的发明，旨在消除药物相关的对宿主的毒性，并增强治疗效果。
• [EN] METABOLICALLY INERT ANTIFOLATES: NEW INDICATIONS AND FORMULATIONS<br/>[FR] ANTIFOLIQUES MÉTABOLIQUEMENT INERTES : NOUVELLES INDICATIONS ET FORMULATIONS
  申请人：NAIR MADHAVAN G

  公开号：WO2010120345A1

  公开（公告）日：2010-10-21

  New metabolism blocked antifolates and their salts are provided along with new indications (coronary heart disease, cardiovascular diseases, stroke and termination of tubal or ectopic pregnancy) and methods (sublingual dosage forms, filmstrips or patches) for their use and delivery. Sublingual dosage forms or trans-dermal patches of metabolically blocked entities of this invention offer superior alternatives to traditional oral dosage forms to achieve greater and predictable therapeutic efficacy, lower toxicity and to overcome drug resistance by virtue of elimination of oxidative deactivation and production of toxic metabolites. Metabolism blocked antifolates bearing a fluorinated benzene ring, a thiophene ring, a pyrrole ring, a furan ring or a 8-deazapteridine ring that are provided in this invention are not previously described. The use of metabolism blocked antifolates to terminate medically complicated pregnancies that are taught herein are new inventions targeted to eliminate drug related toxicity to the host and to enhance therapeutic efficacy.
• Total synthesis of monosporascone and dihydromonosporascone
  作者：Kathryn A. Punch、Matthew J. Piggott

  DOI：10.1039/c4ob00331d

  日期：——

  The first synthesis of monosporascone has been achieved in five steps and 57% overall yield.

  首次合成单孢子酮的过程共分为五个步骤，总产率为57%。
• An Exploratory Study of Type II [3 + 4] Cycloadditions between Vinylcarbenoids and Dienes
  作者：Huw M. L. Davies、Rebecca L. Calvo、Robert J. Townsend、Pingda Ren、R. Melvyn Churchill

  DOI：10.1021/jo991959b

  日期：2000.7.1

  dirhodium tetracarboxylate catalyzed decomposition of vinyldiazoacetates. The [3 + 4] cycloaddition is generally considered to occur by a tandem cyclopropanation/Cope rearrangement, although evidence is presented that with these substrates the [3 + 4] cycloaddition may occur in a concerted manner.

  乙烯基类化合物和呋喃之间的分子内II型[3 + 4]环加成反应是构建5-oxo-10-oxatricyclo [6.2.1.0（4,9）] undeca-3，8（11）-二烯的一种实用方法，包含两个反布雷特双键。这些三环系统功能齐全，可以最终加工成天然产物CP-263,114。铑稳定的乙烯基类胡萝卜素是通过四羧酸二铑催化乙烯基重氮乙酸酯的分解而生成的。通常认为[3 + 4]环加成是通过串联环丙烷化/ Cope重排发生的，尽管有证据表明，使用这些底物，[3 + 4]环加成可能以协同方式发生。