(Z)-ethyl 2-phenyl-5-oxooxazol-4-methylenecarbonate | 291542-21-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-ethyl 2-phenyl-5-oxooxazol-4-methylenecarbonate
• 英文别名: ethyl 2-phenyl-5-oxo-oxazole-4-methylenecarbonate；ethyl [(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl] carbonate
• CAS: 291542-21-7
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: SOQZUGGPAISIMS-NTMALXAHSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  344.4±52.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 2-phenyl-5-oxooxazol-4-methylenecarbonate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到(Z)-2-benzoylamino-3-ethoxycarbonyloxyacrylic acid
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives

  摘要：

  The enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives (5) was studied using the Diels-Alder reaction between cyclopentadiene and different dienophiles, i.e., alkyl 5-oxo-2-phenyloxazol-4-methylenecarbonates (1) or 2-benzoylamino-3-alkoxycarbonyloxy-acrylates. (12), operating with different Lewis acids and both with thermal and with ultrasound conditions. The enantioselective synthesis of the exo/endo compounds 5c,d and 5 'c,d was achieved starting from the chiral menthyl acrylates 12b,c using Mg(ClO4)(2) as the catalyst and ultrasound. The cycloadducts were obtained in very good yield, in mild conditions, in short time, and in good diastereomeric excess (exo, 80%; endo, 87%). Finally, the use of alkylidene-oxazolones or acrylates and EtAlCl2 or Mg(ClO4)(2) as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.

  DOI：

  10.1021/jo010374q
• 作为产物：
  描述：

  氯甲酸乙酯 、 4-hydroxymethylene-2-phenyl-2-oxazolin-5-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(Z)-ethyl 2-phenyl-5-oxooxazol-4-methylenecarbonate
  参考文献：
  名称：

  Conformationally Constrained Serine Analogues:  Synthesis of New 2-Amino-3-hydroxynorbornanecarboxylic Acid Derivatives

  摘要：

  A synthesis of the new oxazolone 2, functionalized with the ethoxycarbonyloxy group on methylenic carbon, is presented, starting from 4-hydroxymethylenoxazolone 1 and ethyl chlorocarbonate. Oxazolone 2 was reacted with cyclopentadiene in the presence of EtAlCl2, giving the two diastereoisomeric cycloadducts exo-3 and endo-3 in a 70:30 ratio. Selective hydrolysis of the lactone ring (THF, HCl) gave the corresponding acids 5 and 6 which were transformed into hydroxyacid derivatives 7 and 8, respectively, operating in an ethanolic solution of Me2NH. The new 3-hydroxy2-aminonorbornane-2-carboxylic acids 11 and 12, in which the serine skeleton is included, were obtained by reduction of acids 5 and 6 to derivatives 9 and 10 and a subsequent hydrolysis with HCl.

  DOI：

  10.1021/jo000595g

文献信息

• Carbocyclic serine analogues: regio- and diastereoselective syntheses of new 1-amino-2,5-dihydroxycyclohexanecarboxylic acids
  作者：Francesca Clerici、Maria Luisa Gelmi、Andrea Gambini、Donatella Nava

  DOI：10.1016/s0040-4020(01)00534-8

  日期：2001.7

  between oxazolone 1 and dienes 2, are the key starting materials for the preparation of β-hydroxycyclohexenamino acid derivatives 4–6. The regio- and diastereoselective functionalization of cyclohexyl ring with a second hydroxy group to give the new 1-amino-2,5-dihydroxycyclohexanecarboxylic acids 11, 19 and the 2,4-dihydroxy derivative 20 was achieved when starting from compounds 4–6. In fact, the iodo-oxazination

  Spirooxazolones 3，恶唑酮之间通过狄尔斯-阿尔德反应获得的1和二烯2，是开始β-hydroxycyclohexenamino酸衍生物的制备材料的关键4 - 6。环己基环的与第二羟基的区域选择性和对映选择性的官能化，得到新的1-氨基-2,5-二羟基环己烷羧酸11，19和2,4-二羟基衍生物20，从化合物开始时所获得4 - 6。实际上，对化合物4的碘代-恶嗪化反应然后，碘原子的还原，导致二羟基氨基酸11，其中两个羟基之间存在顺式关系。碘-内酯化反应，然后还原碘原子，允许从酸5开始形成反式二羟基衍生物19。
• 3-Formylcyclopent-3-enyl- and 3-Carboxycyclopentylglycine Derivatives:  A New Stereocontrolled Approach via Retro-aldol or Retro-Claisen Reactions
  作者：Francesca Clerici、Maria Luisa Gelmi、Sara Pellegrino、Tullio Pilati

  DOI：10.1021/jo030085x

  日期：2003.6.1

  A new synthetic approach to diastereomeric cyclopent-3-enylglycines 19/20, functionalized on the ring with a formyl group, and to cyclopentylglycine, substituted with a carboxy group (compounds 21/22), was devised by applying retro-aldol and retro-Claisen reactions, respectively, to diastereomeric 2-amino-3-ethoxycarbonyloxynorbornene-2-carboxylic acid derivatives 5, 6 and to diastereomeric 2-amin

  通过使用反式醇醛和反式醇醛，设计了一种新的合成方法，用于合成在非对映体上具有甲酰基的环上的非对映体环戊-3-烯基甘氨酸19/20，以及被羧基取代的环戊基甘氨酸（化合物21/22）。对非对映体2-氨基-3-乙氧基羰氧基降冰片烯-2-羧酸衍生物5、6和对非对映体2-氨基-3-氧代-降冰片烷-2-羧酸衍生物的克莱森反应17、18。使用化合物17、18可达到环戊基取代基的顺式立体化学。从17开始并使用丙酮/ DMF中的碳酸氢钠可实现对氨基酸碳的立体化学的部分控制。从exo-17，获得酸22作为主要的非对映异构体。
• A Highly Diastereoselective Synthesis of New Polyhydroxy 2-Aminonorbornanecarboxylic Acids
  作者：Francesca Clerici、Maria Luisa Gelmi、Andrea Gambini

  DOI：10.1021/jo010257v

  日期：2001.7.1