diethyl 3,6-dihydro-3-phenyl-2H-1,3-oxazine-4,5-dicarboxylate | 1132783-30-2

• 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: diethyl 3,6-dihydro-3-phenyl-2H-1,3-oxazine-4,5-dicarboxylate
• 英文别名: diethyl 3-phenyl-3,6-dihydro-2H-[1,3]oxazine-4,5-dicarboxylate；Diethyl 3-phenyl-2,6-dihydro-1,3-oxazine-4,5-dicarboxylate；diethyl 3-phenyl-2,6-dihydro-1,3-oxazine-4,5-dicarboxylate
• CAS: 1132783-30-2
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: XWOVNFCMFSPLAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 苯胺 、 丁炔二酸二乙酯 在 ytterbium(III) triflate hydrate 作用下， 以 水 为溶剂， 反应 6.0h， 以70%的产率得到diethyl 3,6-dihydro-3-phenyl-2H-1,3-oxazine-4,5-dicarboxylate
  参考文献：
  名称：

  三氟甲磺酸镱促进3,4,5-三取代-3,6-二氢-2H-1,3-恶嗪的一锅法三组分合成

  摘要：

  描述了一种从乙炔二羧酸盐、芳香族和脂肪族胺以及甲醛中高效一锅法合成 3,4,5-三取代-3,6-二氢-2H-1,3-恶嗪的方法。通过 Yb(OTf)3 促进的多米诺加氢胺化/Prins 反应/环化/脱水反应构建了六元 N,O-杂环核。 

  DOI：

  10.1007/s10562-011-0605-3

文献信息

• l-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines
  作者：Huanfeng Jiang、Ronghuan Mai、Hua Cao、Qiuhua Zhu、Xiaohang Liu

  DOI：10.1039/b914659h

  日期：——

  Highly functionalized multisubstituted 1,4-dihydropyridines 5 have been concisely synthesized in moderate to good yields viaL-proline-catalyzed one-pot multicomponent reactions (MCRs) of alkynoates or alkynones 1, amines 2, β-dicarbonyl compounds 3 and aldehydes 4 under mild conditions. The MCR process involves hydroamination/Knoevenagel condensation/Michael-type addition/intramolecular cyclization

  高度精巧地通过L-合成了高度官能化的多取代1,4-二氢吡啶5。脯氨酸炔烃或炔烃1，胺2，β-二羰基化合物3和醛4在温和的条件下。MCR过程涉及加氢胺化/ Knoevenagel缩合/ Michael型加成/分子内环化过程，并导致形成1,4-二氢吡啶5。通过单晶X射线衍射确认了5ckaa的分子结构。该方法节能环保，可轻松获得各种多取代的多官能多官能1,4-二氢吡啶。
• Ytterbium Triflate Promoted One-Pot Three Component Synthesis of 3,4,5-Trisubstituted-3,6-dihydro-2H-1,3-oxazines
  作者：Francesco Epifano、Caroline Pelucchini、Ornelio Rosati、Salvatore Genovese、Massimo Curini

  DOI：10.1007/s10562-011-0605-3

  日期：2011.6

  An efficient one-pot synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazines from acetylene dicarboxylates, aromatic and aliphatic amines, and formaldehyde is described. The six member N,O-heterocyclic nucleus was constructed via Yb(OTf)3 promoted domino hydroamination/Prins reaction/cyclization/dehydration reactions.Graphical Abstract 

  描述了一种从乙炔二羧酸盐、芳香族和脂肪族胺以及甲醛中高效一锅法合成 3,4,5-三取代-3,6-二氢-2H-1,3-恶嗪的方法。通过 Yb(OTf)3 促进的多米诺加氢胺化/Prins 反应/环化/脱水反应构建了六元 N,O-杂环核。 
• Synthesis of substituted 1,3-oxazines using sulfamic acid as an efficient and eco-friendly catalyst
  作者：M. Damodiran、Paramasivan T. Perumal

  DOI：10.1002/jhet.489

  日期：2010.11

  Sulfamic acid catalyzed the synthesis of substituted 1,3‐oxazines by one‐pot three‐component reaction of aniline, alkynoates, and formaldehyde in excellent yields. The catalyst possesses distinct advantages shows ease of handling, good yields, cleaner reactions, nonhygroscopic, noncorrosive, and high activity. Sulfamic acid is a green alternative for metal‐containing acidic materials, which are toxic

  氨基磺酸通过苯胺，炔酸和甲醛的一锅三组分反应催化合成1,3-恶嗪，收率很高。该催化剂具有明显的优点，显示出易于处理，良好的收率，更清洁的反应，不吸湿，无腐蚀性和高活性。氨基磺酸是一种绿色的替代品，可替代含金属的酸性物质，这种物质对人类健康和环境保护都是有毒有害的。J.杂环化​​学。（2010）。
• Brønsted acid-promoted domino reactions: a novel one-pot three-component synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazines
  作者：Hua Cao、Huan-Feng Jiang、Chao-Rong Qi、Wen-Juan Yao、Huo-Ji Chen

  DOI：10.1016/j.tetlet.2009.01.002

  日期：2009.3

  An efficient and novel one-pot synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazine from alkynoates, anilines, and formaldehyde is described. The six-membered N,O-heterocyclic skeleton was constructed via Brønsted acid-promoted domino hydroamination/Prins reaction/cyclization/dehydration reactions.

  描述了一种高效，新颖的一锅合成法，从炔酸，苯胺和甲醛合成3,4,5-三取代-3,6-二氢-2 H -1,3-恶嗪。通过布朗斯台德酸促进的多米诺加氢胺化/ Prins反应/环化/脱水反应构建了六元的N，O杂环骨架。
• Si-OSO3H catalyzed one-pot three-component synthesis of 1,3-oxazines
  作者：S. Sudha、M. A. Pasha

  DOI：10.1007/s13738-014-0423-9

  日期：2014.12

  A simple and an efficient method for the synthesis of six membered nitrogen containing heterocyclic compounds—1,3-oxazines from diethyl acetylene dicarboxylate, substituted anilines or amines and formaldehyde is reported. A versatile, economical and eco-friendly heterogeneous reagent silica sulfuric acid (Si-OSO3H) is used as a catalyst for this reaction.

  报告采用了一种简单高效的方法，从乙炔二羧酸二乙酯、取代苯胺或胺和甲醛中合成六位含氮杂环化合物-1,3-噁嗪。该反应使用了一种多功能、经济、环保的异相试剂二氧化硅硫酸（Si-OSO3H）作为催化剂。