2-benzyl-4-ethoxymethylene-5-oxazolone | 61369-26-4

• 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: 2-benzyl-4-ethoxymethylene-5-oxazolone
• 英文别名: 4-ethoxymethylene-2-benzyl-4H-oxazol-5-one；4-Aethoxymethylen-2-benzyl-4H-oxazol-5-on；2-benzyl-4-ethoxymethylene-5-oxazolinone；4-ethoxymethylene-2-benzyl-5-azlactone；5(4H)-Oxazolone, 4-(ethoxymethylene)-2-(phenylmethyl)-；2-benzyl-4-(ethoxymethylidene)-1,3-oxazol-5-one
• CAS: 61369-26-4
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: KDXYERQLMHLLJT-UHFFFAOYSA-N

物化性质

• 沸点：
  336.9±52.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 2-benzyl-4-ethoxymethylene-5-oxazolone 生成 N-(2-morpholin-4-yl-2-oxo-ethyl)-2-phenyl-acetamide
  参考文献：
  名称：

  Cornforth, Chemistry of Penicillin

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-2-(C-phenyl-acetylamino)-3.3-diethoxy-propionic acid 在 三溴化磷 作用下， 生成 2-benzyl-4-ethoxymethylene-5-oxazolone
  参考文献：
  名称：

  Cornforth, Chemistry of Penicillin

  摘要：

  DOI：

文献信息

• Production method of pyrimidine derivative, intermediate therefor
  申请人：Ajinomoto Co., Inc.

  公开号：EP1529778A1

  公开（公告）日：2005-05-11

  The present invention relates to a production method of compound (XV), which includes hydrolysis of compound (I) to give compound (II), then reaction with reagent (III) to give compound (IV), then reaction with compound (V) to give compound (VI), then condensation with compound (XII) to give compound (XI), and preferably deprotection by an enzyme reaction. This method is an advantageous production method of a pyrimidine derivative and a synthetic intermediate useful as an enzyme inhibitor. wherein P is an alkyl group and the like, M is sodium and the like, R1 and R2 are each an alkyl group and the like, R3 is an alkyl group optionally having substituent(s) and the like, X is a halogen atom and the like, R5 is an alkyl group optionally having substituent(s) and the like, R6 is a hydrogen atom and the like, R7 is an aralkyl group optionally having substituent(s) and the like, and Y is a heteroaryl group optionally having substituents and the like.

  本发明涉及一种化合物（XV）的生产方法，包括将化合物（I）水解得到化合物（II），然后与试剂（III）反应得到化合物（IV），然后与化合物（V）反应得到化合物（VI），然后与化合物（XII）缩合得到化合物（XI），最好通过酶反应脱保护。该方法是一种有利的嘧啶衍生物和合成中间体的生产方法，可用作酶抑制剂。其中P是烷基等，M是钠等，R1和R2分别是烷基等，R3是可选地具有取代基的烷基等，X是卤素原子等，R5是可选地具有取代基的烷基等，R6是氢原子等，R7是可选地具有取代基的芳基烷基等，Y是可选地具有取代基的杂环芳基等。
• An Improved Synthesis of 5-Acylamino-6-oxo-2-phenyl-1(6H)-pyrimidineacetic Acid from Glycine with Readily Removable Protecting Groups
  作者：Daisuke Takahashi、Kunisuke Izawa、Tatsumi Kashiwagi、Hiromi Onoye、Robert M. Williams

  DOI：10.3987/com-12-12518

  日期：——

  Concise synthesis of N-acyl-5-amino-6-oxo-2-phenyl-1(6H)-yrimidineacetic acid was achieved by cyclization reaction of 2-alkyl-4-lkoxymethylene-5(4H)-oxazolone with N-(carboxymethyl)benzamidine, while a similar reaction with sodium salt of 2-alkyl-4-hydroxymethylene-5(4H)-xazolones gave a mixture of regioisomers of the pyrimidinone. N-Acyl groups (acetyl or phenylacetyl) of the pyrimidinone derivatives were readily cleaved under very mild conditions with weak base or enzyme. Thus, the process enabled us to synthesize the drug candidate without exchanging N-protecting group. Since the starting oxazolones were easily prepared from N-acylglycine, the synthetic route can be used for the large scale synthesis of the key intermediate for several enzyme inhibitors.
• Tsukita, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1949, vol. 69, p. 102
  作者：Tsukita

  DOI：——

  日期：——
• EP1553090
  申请人：——

  公开号：——

  公开（公告）日：——
• US2483530
  申请人：——

  公开号：——

  公开（公告）日：——