3-benzyl-2-oxo-2,3-dihydro-oxazole-5-carbaldehyde | 64843-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyl-2-oxo-2,3-dihydro-oxazole-5-carbaldehyde
• 英文别名: 3-Benzyl-2-oxo-1,3-oxazole-5-carbaldehyde
• CAS: 64843-30-7
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: OLCJVWHZEMLSKE-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  338.2±52.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄基-2-丙炔胺 在 碘 、 氧气 、 四甲基胍 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 3-benzyl-2-oxo-2,3-dihydro-oxazole-5-carbaldehyde
  参考文献：
  名称：

  Metal‐Free Photocatalytic Synthesis of exo ‐Iodomethylene 2‐Oxazolidinones: An Alternative Strategy for CO ₂ Valorization with Solar Energy

  摘要：

  AbstractA visible‐light‐promoted metal‐free carboxylative cyclization of propargylic amines with CO2 was shown to offer exo‐iodomethylene 2‐oxazolidinones. Incorporation of both CO2 and iodo moieties into these compounds was realized efficiently. The mechanism study revealed that this carboxylative cyclization proceeds through a radical pathway. Notably, the iodine‐functionalized 2‐oxazolidinone as a platform molecule could be easily converted into a wide range of value‐added chemicals through Buchwald–Hartwig, Suzuki, Sonogashira, photocatalytic ene, and photoreduction reactions. As a result, the plentiful downstream transformations remarkably enhance the range of chemicals derived from CO2 and open a potential avenue for CO2 functionalization to circumvent energy challenges in this field.

  DOI：

  10.1002/cssc.201902417

文献信息

• Facile conversion of 4-halogeno-1,3-dioxolan-2-ones to 2-oxazolidones.
  作者：TSUTOMU MATSUURA、TAKEHISA KUNIEDA、TAKEO TAKIZAWA

  DOI：10.1248/cpb.25.1225

  日期：——

  Telomers of vinylenecarbonate with tetrachloromethane, which possess the 4-chloro-1, 3-dioxolan-2-one structure as a terminal ring, underwent smooth and selective conversion with primary aliphatic amines into 5-substituted 4-hydroxy-2-oxazolidones whose chemical reactions with the aid of acids, dehydration and phenylation, led to the corresponding 4-oxazolin-2-ones and 4-phenyl-2-oxazolidones, respectively. Treatment of 5-trichloromethyl-2-oxazolidinone with zinc-methanol resulted in the exclusive formation of 5-dichloromethyl-2-oxazolidone, in contrast to the corresponding 1, 3-dioxolan-2-one system which suffered complete reductive ring-opening even under milder conditions.

  碳酸亚乙烯基酯与四氯甲烷的调聚物具有 4-氯-1, 3-二氧戊环-2-酮结构作为端环，与脂肪伯胺顺利且选择性地转化为 5-取代的 4-羟基-2-恶唑烷酮，其化学性质借助酸、脱水和苯化反应，分别生成相应的4-恶唑啉-2-酮和4-苯基-2-恶唑烷酮。用锌-甲醇处理 5-三氯甲基-2-恶唑烷酮导致仅形成 5-二氯甲基-2-恶唑烷酮，而相应的 1, 3-二氧杂环戊烷-2-酮系统甚至会完全还原开环。在较温和的条件下。
• MATSUURA T.; KUNIEDA T.; TAKIZAWA T., CHEM. AND PHARM. BULL. <CPBT-AL>, 1977, 25, NO 6, 1225-1229
  作者：MATSUURA T.、 KUNIEDA T.、 TAKIZAWA T.

  DOI：——

  日期：——
• Metal‐Free Photocatalytic Synthesis of <i>exo</i> ‐Iodomethylene 2‐Oxazolidinones: An Alternative Strategy for CO ₂ Valorization with Solar Energy
  作者：Xing He、Xiang‐Yang Yao、Kai‐Hong Chen、Liang‐Nian He

  DOI：10.1002/cssc.201902417

  日期：2019.12.6

  AbstractA visible‐light‐promoted metal‐free carboxylative cyclization of propargylic amines with CO2 was shown to offer exo‐iodomethylene 2‐oxazolidinones. Incorporation of both CO2 and iodo moieties into these compounds was realized efficiently. The mechanism study revealed that this carboxylative cyclization proceeds through a radical pathway. Notably, the iodine‐functionalized 2‐oxazolidinone as a platform molecule could be easily converted into a wide range of value‐added chemicals through Buchwald–Hartwig, Suzuki, Sonogashira, photocatalytic ene, and photoreduction reactions. As a result, the plentiful downstream transformations remarkably enhance the range of chemicals derived from CO2 and open a potential avenue for CO2 functionalization to circumvent energy challenges in this field.