(2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid methyl ester | 33350-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid methyl ester
• 英文别名: Methyl (2E)-2-(9-oxo-10-oxa-7-azabicyclo[4.4.0]deca-1,3,5-trien-8-ylidene)acetate；methyl 2-(2-oxo-4H-1,4-benzoxazin-3-ylidene)acetate
• CAS: 33350-83-3
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: HYUHHJZPKDHFRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid methyl ester 以 正己烷 为溶剂， 反应 24.0h， 生成 rac-methyl (7aR,8R,10aS)-8-(4-bromophenyl)-6,7,11-trioxo-9-phenyl-6,7,8,9-tetrahydro-7aH,11H-[1,2]oxazolo[5′,4′:2,3]pyrrolo[2,1-c][1,4]-benzoxazine-7a-carboxylate
  参考文献：
  名称：

  Dipolar [3+2]-Cycloaddition of Nitrones to 3-Alkoxycarbonyl- and 3-Pivaloyl-Substituted Hetareno[e]pyrrole-2,3-diones

  摘要：

  DOI：

  10.1134/s1070428022030058
• 作为产物：
  描述：

  2-氨基苯酚 、 丁炔二酸二甲酯 以 甲醇 为溶剂， 反应 0.08h， 以97%的产率得到(2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid methyl ester
  参考文献：
  名称：

  An Efficient Synthesis of Functionalized 6,10-Dioxo-6,10-dihydro-5H-pyrido[1,2-a]quinoxalines and 6,10-Dioxo-6,10-dihydropyrido[2,1-c][1,4]benz­oxazines

  摘要：

  介绍了一种 8-羟基-6,10-二氧代-6,10-二氢-5H-吡啶并[1,2-a]喹喔啉-7-羧酸烷基酯和 8-羟基-6,10-二氧代-6,10-二氢吡啶并[2,1-c][1,4]苯并恶嗪-7-羧酸烷基酯的高效合成方法。这涉及丙二酰氯与 2-[3,4-二氢-3-氧代喹喔啉-2(1H)-亚基]乙酸烷基酯或 2-(2-氧代-2H-苯并[b][1,4]恶嗪-3(4H)-亚基)乙酸烷基酯在 CH2Cl2 中于室温下的反应。

  DOI：

  10.1055/s-0029-1217542

文献信息

• Novel Approach for the Synthesis of Pyrrolo[2,1-c][1,4]Benzoxazines and Pyrrolo[1,2-a]Quinoxalines
  作者：Tayebeh Sanaeishoar、Somayeh Adibi-Sedeh、Saghar Karimian

  DOI：10.2174/1386207316666131227150430

  日期：2014.1.31

  An efficient synthesis of alkyl 4,5-dihydro-4-oxo-2-phenylpyrrolo[2,1-c][1,4]benzoxazine-3-carboxylates and alkyl 4,5-dihydro-4-oxo-2-phenylpyrrolo[1,2-a]quinoxaline-3-carboxylates is described. This involves a three-component reaction between o-aminophenols or o-phenylenediamine, acetylenic esters and β-nitrostyrene derivatives using p-toluene sulfonic acid as a catalyst.

  有效合成烷基4,5-二氢-4-氧代-2-苯基吡咯并[2,1-c] [1,4]苯并恶嗪-3-羧酸酯和烷基4,5-二氢-4-氧代-2-苯基吡咯并描述了[1,2-a]喹喔啉-3-羧酸盐。这涉及使用对甲苯磺酸作为催化剂的邻氨基苯酚或邻苯二胺，炔属酯和β-硝基苯乙烯衍生物之间的三组分反应。
• Trifluoroacetic acid-promoted Michael addition–cyclization reactions of vinylogous carbamates
  作者：Ram Tilak Naganaboina、Amrita Nayak、Rama Krishna Peddinti

  DOI：10.1039/c4ob00437j

  日期：——

  A simple and efficient methodology has been developed for the synthesis of pyrrolobenzoxazine and 3-arylamino coumarin derivatives promoted by trifluoroacetic acid. The initial step in the current protocol involves a Michael addition of the 1,4-benzoxazinone derivatives to the Michael acceptors and subsequent cyclization.

  已开发出一种简单高效的方法，通过三氟乙酸促进合成吡咯苯并噁嗪和3-芳基氨基香豆素衍生物。当前方案的初始步骤涉及1,4-苯并噁嗪衍生物与Michael受体的Michael加成，然后进行环化反应。
• BF₃·OEt₂-Mediated Synthesis of 2-Arylthio- and (<i>N</i>-Aryl-2,5-dioxopyrrolidin-3-yl)-Substituted 1,4-Benzoxazine Derivatives
  作者：Shivangi Sharma、Pravin Kumar、Arun Sharma、Rama Krishna Peddinti

  DOI：10.1002/ejoc.201700407

  日期：2017.6.8

  1,4-Benzoxazines have been explored as versatile precursors for the synthesis of novel benzoxazine and benzoxazinone derivatives. 2-Hydroxy-1,4-benzoxazines and 1,4-benzoxazinones have been functionalized with thiols and N-arylmaleimides, respectively, in the presence of BF3·OEt2 as a promoter. All the products were obtained in moderate to excellent yields. The Michael reactions of the benzoxazinones

  1,4-苯并恶嗪已被用作合成新型苯并恶嗪和苯并恶嗪酮衍生物的通用前体。在BF3·OEt2作为促进剂存在下，2-羟基-1,4-苯并恶嗪和1,4-苯并恶嗪分别被硫醇和N-芳基马来酰亚胺官能化。所有产品均以中等至极好的收率获得。苯并嗪酮与马来酰亚胺的迈克尔反应提供了加合物的非对映异构混合物，其特征在于标准光谱方法。
• FeCl₃-Mediated Domino Reaction of Benzoxazinones with Aroylmethylidene Malonates: Synthesis to Functionalized Pyrrolobenzoxazines
  作者：Shweta Bisht、Rama Krishna Peddinti

  DOI：10.1021/acs.joc.7b02207

  日期：2017.12.15

  efficient domino approach for the synthesis of pyrrolobenzoxazine derivatives is described. The FeCl3-promoted domino reaction between aroylmethylidene malonates and benzoxazinones has been successfully established to afford the title compounds in good to excellent yield under mild reaction conditions. The domino protocol provides a concise and straightforward access to highly substituted pyrrolobenzoxazines

  描述了一种用于合成吡咯并苯并恶嗪衍生物的有效多米诺方法。已经成功地建立了芳基亚甲基丙二酸酯和苯并恶嗪酮之间的FeCl 3促进的多米诺反应，以在温和的反应条件下以良好或优异的收率提供标题化合物。多米诺协议提供了简洁，直接的途径，可以高效，出色的官能团耐受性来直接访问高度取代的吡咯并苯并恶嗪。
• Zn(OTf)2-Catalyzed 1,6-Conjugate Addition of Benzoxazinones to p-Quinone Methides: Access to 3,3-Diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic Acid Esters
  作者：Rama Krishna Peddinti、Neha Dua、Sonali Ghosh

  DOI：10.1055/s-0040-1706600

  日期：2021.3

  An effective method for the synthesis of 3,3-diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic acid esters is reported. A novel zinc triflate-catalyzed regioselective 1,6-conjugate addition of vinylogous carbamates to p-quinone methides for accessing the title compounds has been developed. This protocol furnished the hybrid compounds in good to excellent yields. The reaction is rapid and has a broad

  报道了一种合成3,3-二芳基-2-（2-氧代-2 H -1,4-苯并恶嗪-3-基）丙酸酯的有效方法。已经开发了一种新的三氟甲磺酸锌催化的乙烯基氨基甲酸酯向对苯醌甲基化物的区域选择性的1,6-共轭加成，以得到标题化合物。该方案为杂种化合物提供了良好的优良收率。该反应是快速的并且具有广泛的底物范围。