乙基6H-1,2-恶嗪-3-羧酸酯 | 185223-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 中文名称: 乙基6H-1,2-恶嗪-3-羧酸酯
• 英文名称: Ethyl 6H-1,2-oxazine-3-carboxylate
• 英文别名: ethyl 6H-oxazine-3-carboxylate
• CAS: 185223-40-9
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: VEDAJFIVJOLMQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  乙基6H-1,2-恶嗪-3-羧酸酯 在 potassium permanganate 、 水 、 magnesium sulfate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (4S,5R)-4,5-Dihydroxy-5,6-dihydro-4H-[1,2]oxazine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Stereoselective Preparation of 4,5-Dihydroxy-5,6-dihydro-4H-1,2-oxazines and Their Derivatives

  摘要：

  cis-Dihydroxylation of 6H-1,2-oxazines 1 proceeds efficiently either by potassium permanganate at low temperature (Method A) or by ruthenium trichloride/sodium periodate at 0-5 degrees C (Method B). The resulting 4,5-dihydroxylated 1,2-oxazines 2 were usually obtained as diastereomerically pure compounds with the two newly introduced hydroxy groups positioned trans to the 6-alkoxy group. These products can be protected by standard methods either as acetals 4 or as diacetoxy compounds 5. In addition, the bicyclic orthoesters 7 and 8, dimesylates 15, and cyclic sulfates 19 have been prepared. First experiments dealing with transformations of the oxygen functionalities are described.

  DOI：

  10.1055/s-1999-3524
• 作为产物：
  描述：

  (E)-ethyl 2-oxo-3-pentenoate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 盐酸羟胺 、 potassium carbonate 作用下， 以 四氯化碳 为溶剂， 反应 9.5h， 生成 乙基6H-1,2-恶嗪-3-羧酸酯
  参考文献：
  名称：

  通过Heck环化作用的吲哚-3-丙酮酸肟醚和噻吩类似物。在合成硫氨酸-色氨酸中的应用

  摘要：

  Ñ的-allylation Ñ -BOC取代ø碘苯胺（14A-E ）和thienoamines（16,18,20）采用乙基的甲基或苄基的肟醚（E）-2-氧代-5-溴-3-戊烯酸酯2A然后，钯催化的Heck环化反应生成Bz取代的乙基吲哚-3-丙酮酸酯（15a-f）和噻吩并吡咯（17,19,21–23）的肟醚。尝试将2a转化为相应的甲苯磺隆hydr或肟导致形成哒嗪（10）和恶嗪（13）衍生产品。通过还原肟双键，从相应的甲基肟醚中获得作为乙基酯的噻吨-色氨酸的三种可能的异构体。

  DOI：

  10.1016/0040-4020(96)00909-x

文献信息

• Stereoselective Preparation of 4,5-Dihydroxy-5,6-dihydro-4H-1,2-oxazines and Their Derivatives
  作者：Reinhold Zimmer

  DOI：10.1055/s-1999-3524

  日期：1999.7

  cis-Dihydroxylation of 6H-1,2-oxazines 1 proceeds efficiently either by potassium permanganate at low temperature (Method A) or by ruthenium trichloride/sodium periodate at 0-5 degrees C (Method B). The resulting 4,5-dihydroxylated 1,2-oxazines 2 were usually obtained as diastereomerically pure compounds with the two newly introduced hydroxy groups positioned trans to the 6-alkoxy group. These products can be protected by standard methods either as acetals 4 or as diacetoxy compounds 5. In addition, the bicyclic orthoesters 7 and 8, dimesylates 15, and cyclic sulfates 19 have been prepared. First experiments dealing with transformations of the oxygen functionalities are described.
• Indole-3-pyruvic acid oxime ethers and thieno analogues by Heck cyclisation. Application to the synthesis of thia-tryptophans
  作者：David Wensbo、Salo Gronowitz

  DOI：10.1016/0040-4020(96)00909-x

  日期：1996.11

  thienoamines (16,18,20) employing methyl or benzyl oxime ethers of ethyl (E)-2-oxo-5-bromo-3-pentenoate 2a, followed by palladium-catalysed Heck cyclisation yielded oxime ethers of Bz-substituted ethyl indole-3-pyruvates (15a-f) and thienopyrroles (17,19,21–23). Attempted conversion of 2a into the corresponding tosyl hydrazone or oxime resulted in formation of pyridazine (10) and oxazine (13) derivatives.

  Ñ的-allylation Ñ -BOC取代ø碘苯胺（14A-E ）和thienoamines（16,18,20）采用乙基的甲基或苄基的肟醚（E）-2-氧代-5-溴-3-戊烯酸酯2A然后，钯催化的Heck环化反应生成Bz取代的乙基吲哚-3-丙酮酸酯（15a-f）和噻吩并吡咯（17,19,21–23）的肟醚。尝试将2a转化为相应的甲苯磺隆hydr或肟导致形成哒嗪（10）和恶嗪（13）衍生产品。通过还原肟双键，从相应的甲基肟醚中获得作为乙基酯的噻吨-色氨酸的三种可能的异构体。