2-丙-1-烯-2-基-1,3-恶唑-4-羧酸乙酯 | 618884-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-丙-1-烯-2-基-1,3-恶唑-4-羧酸乙酯
• 英文名称: ethyl 2-(prop-1-en-2-yl)oxazole-4-carboxylate
• 英文别名: Ethyl 2-(prop-1-en-2-yl)-1,3-oxazole-4-carboxylate；ethyl 2-prop-1-en-2-yl-1,3-oxazole-4-carboxylate
• CAS: 618884-47-2
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: XXAPYMFOKIMWES-UHFFFAOYSA-N

物化性质

• 沸点：
  268.8±32.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-丙-1-烯-2-基-1,3-恶唑-4-羧酸乙酯 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以78%的产率得到2-Isopropenyloxazole-4-carboxylic acid
  参考文献：
  名称：

  One-Pot Multistep Bohlmann−Rahtz Heteroannulation Reactions:  Synthesis of Dimethyl Sulfomycinamate

  摘要：

  The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.

  DOI：

  10.1021/jo048106q
• 作为产物：
  描述：

  4-羟基-2-(2-丙烯基)-2-恶唑啉-4-羧酸乙酯 在 2,6-二甲基吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到2-丙-1-烯-2-基-1,3-恶唑-4-羧酸乙酯
  参考文献：
  名称：

  Synthesis of Dimethyl Sulfomycinamate

  摘要：

  Dimethyl sulfomycinamate, the oxazole-thiazole-pyridine product generated in the methanolysis of the thiopeptide antibiotic sulfomycin 1, is prepared in 13 steps and 8% overall yield by the Bohlmann-Rahtz heteroannulation of 1-(oxazol-4-yl)enamines and methyl 4-(trimethylsilyl)2-oxobut-3-ynoate.

  DOI：

  10.1021/ol0357144

文献信息

• Direct palladium-catalyzed alkenylation, benzylation and alkylation of ethyl oxazole-4-carboxylate with alkenyl-, benzyl- and alkyl halides
  作者：Cécile Verrier、Christophe Hoarau、Francis Marsais

  DOI：10.1039/b816374j

  日期：——

  The ethyl oxazole-4-carboxylate was directly and regioselectively alkenylated, benzylated and alkylated with alkenyl-, benzyl-, allyl- and alkyl halides in the presence of catalytic amounts of palladium acetate with caesium carbonate using Buchwald's JohnPhos ligand.

  这 恶唑-4-羧酸乙酯 在催化量的四氢呋喃存在下，用烯基-，苄基-，烯丙基-和烷基卤化物直接和区域选择性地进行烯基化，苄基化和烷基化。 醋酸钯 使用布赫瓦尔德（Buchwald）的JohnPhos配体制备碳酸铯
• Synthesis of Dimethyl Sulfomycinamate
  作者：Mark C. Bagley、James W. Dale、Xin Xiong、Justin Bower

  DOI：10.1021/ol0357144

  日期：2003.11.1

  Dimethyl sulfomycinamate, the oxazole-thiazole-pyridine product generated in the methanolysis of the thiopeptide antibiotic sulfomycin 1, is prepared in 13 steps and 8% overall yield by the Bohlmann-Rahtz heteroannulation of 1-(oxazol-4-yl)enamines and methyl 4-(trimethylsilyl)2-oxobut-3-ynoate.
• One-Pot Multistep Bohlmann−Rahtz Heteroannulation Reactions:  Synthesis of Dimethyl Sulfomycinamate
  作者：Mark C. Bagley、Krishna Chapaneri、James W. Dale、Xin Xiong、Justin Bower

  DOI：10.1021/jo048106q

  日期：2005.2.1

  The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.