3-Azido-4-chromanone | 155060-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-Azido-4-chromanone
• 英文别名: 3-azidochroman-4-one；4H-1-Benzopyran-4-one, 3-azido-2,3-dihydro-；3-azido-2,3-dihydrochromen-4-one
• CAS: 155060-17-6
• 化学式: C₉H₇N₃O₂
• 分子量: 189.173
• InChiKey: IZHKRIBZZHYXGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Azido-4-chromanone 在 TEA 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 101.0h， 生成 (3S,3'R)-3'-methylspiro[2H-chromene-3,2'-aziridine]-4-one
  参考文献：
  名称：

  Base-Induced Coupling of α-Azido Ketones with Aldehydes − An Easy and Efficient Route to Trifunctionalized Synthons 2-Azido-3-hydroxy Ketones, 2-Acylaziridines, and 2-Acylspiroaziridines

  摘要：

  DOI：

  10.1002/1099-0690(20021)2002:2<285::aid-ejoc285>3.0.co;2-j
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 在 sodium azide 、 18-冠醚-6 、 溴 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 3-Azido-4-chromanone
  参考文献：
  名称：

  Base-Induced Coupling of α-Azido Ketones with Aldehydes − An Easy and Efficient Route to Trifunctionalized Synthons 2-Azido-3-hydroxy Ketones, 2-Acylaziridines, and 2-Acylspiroaziridines

  摘要：

  DOI：

  10.1002/1099-0690(20021)2002:2<285::aid-ejoc285>3.0.co;2-j

文献信息

• Bifunctional squaramide catalyzed stereoselective Mannich reaction of α-azido ketones with isatin-derived ketimines
  作者：Seda Karahan、Cihangir Tanyeli

  DOI：10.1039/c9ob02208b

  日期：——

  Asymmetric organocatalytic Mannich reaction of α-azido ketones and N-Boc protected isatin-derived ketimines were investigated for the first time. Examination of both 2-adamantyl and 3,5-bis(trifluoromethyl)aniline substituted quinine-based squaramides afforded chiral Mannich bases with two contiguous stereogenic centers in high yields (up to 97%) and stereoselectivity (up to dr = 24 : 1 syn : anti

  首次研究了α-叠氮基酮与N-Boc保护的由靛红衍生的酮亚胺的不对称有机催化曼尼希反应。检验2-金刚烷基和3,5-双（三氟甲基）苯胺取代的奎宁为基础的方酰胺，可得到具有两个连续立体生成中心的手性曼尼希碱，产率高（高达97％）和立体选择性（高达dr = 24：1 syn ：anti和96％ee）。在代表性实例中利用了强杂环前体加合物的叠氮基和掩蔽的氨基官能团。
• α-Azido Ketones, Part 8: Base-Induced Coupling of α-Azido Ketones with a 1,2-Diaza-1,3-diene as a Michael Acceptor
  作者：Tamás Patonay、Éva Juhász-Tóth、Gianfranco Favi、Orazio Attanasi、Attila Bényei

  DOI：10.1055/s-0033-1338655

  日期：——

  Carbanions generated from various acyclic and cyclic α-azido ketones in the presence of bases were reacted with ethyl 3-[(carbamoylimino)amino]but-2-enoate as a Michael acceptor to give the corresponding adducts. The adducts of acyclic azides were unstable and eliminated hydrazoic acid to give the corresponding ethyl 2-[1-[(carbamoylamino)imino]ethyl]-4-oxo-4-phenylbut-2- enoates as (E,E/Z,E)-diastereomeric

  在碱存在下，由各种无环和环状 α-叠氮酮生成的碳负离子与作为迈克尔受体的 3-[(氨基甲酰基亚氨基)氨基]丁-2-烯酸乙酯反应，得到相应的加合物。无环叠氮化物的加合物不稳定并消除了重氮酸，得到相应的 2-[1-[(氨基甲酰氨基)亚氨基]乙基]-4-氧代-4-苯基丁-2-烯酸乙酯，如 (E,E/Z,E )-非对映体混合物。这些非对映异构体的相对构型通过 X 射线分析确定。除 2-叠氮苯并丁酮外，环状 α-叠氮酮的加合物以非对映异构纯形式获得。
• Diastereoselective Aldol Reaction of α‐Azido Ketones with α‐CF3 Pyruvate to Organoazides with Vicinal Tetrasubstituted Carbons
  作者：Yang Gao、Xue‐Xin Zhang、Zhi Tu、Jin‐Sheng Yu、Jian Zhou

  DOI：10.1002/ejoc.202400348

  日期：2024.7.8

  An organocatalytic direct aldol reaction of α-azido ketones and α-trifluoromethyl pyruvate for the diastereoselective synthesis of β-CF3 organoazides with contiguous tetrasubstituted carbons is described, providing access to valuable multifunctional trifluoromethyl organoazides in good to excellent yields, with moderate diastereoselectivities.

  描述了 α-叠氮酮和 α-三氟甲基丙酮酸的有机催化直接醇醛缩合反应，用于非对映选择性合成具有连续四取代碳的 β-CF 3 有机叠氮化物，从而以良好至优异的收率获得有价值的多功能三氟甲基有机叠氮化物，具有中等的非对映选择性。
• Base-Promoted Reactions of .alpha.-Azido Ketones with Aldehydes and Ketones: A Novel Entry to .alpha.-Azido-.beta.-hydroxy Ketones and 2,5-Dihydro-5-hydroxyoxazoles
  作者：Tamas Patonay、Robert V. Hoffman

  DOI：10.1021/jo00113a015

  日期：1995.4

  The base-promoted reaction of alpha-azido ketones with aldehydes and ketones provides a new and simple route to either alpha-azido-beta-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction, The alpha-azido-beta-hydroxy ketones are formed by an aldol reaction between an enolate of the alpha-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the cx-azido ketone enolate.
• A General and Efficient Synthesis of .alpha.-Azido Ketones
  作者：Tamos Patonay、Robert V. Hoffman

  DOI：10.1021/jo00089a043

  日期：1994.5